Question 1

You Made This.

March 10, 2026

You Made This.

From bitching to building, 8 years of B2SMBI

The birth of the B2SMB Institute started as a bitch session.

Actually, multiple bitch sessions. Over years.

In dozens of locations across the country. With dozens of people, always in small groups, always in what felt like the same conference room.

The bitch sessions always had the same players – really, the same job titles – represented in every location. Usually 5-6 attendees at a time.

And I was the only common thread.

The Players were all clients: Advertisers and Sponsors of bizHive.com.

I had started bizHive in 2011 with my co-Founder, Derick Thompson. It was what seemed an innovation at the time: an “informational marketplace” for Small Business.

The platform guided Small Business users from a moment of need or an item on a to-do list to a specific solution. The solutions were offered by our Advertisers and Sponsors, who paid us for the Small Business’ interest in “getting a job done” on a per-lead basis.

Hence the need for me to travel around the country and meet with those who would and did buy said leads from us.

It was on those travels – from Microsoft in Seattle to Austin for Dell to Kansas City and Sprint – I met a host of Execs charged with selling to Small Businesses at scale.

But as different as all of the brands and offerings represented in these meetings were, the bitch session was always the same:

“Small Businesses are so hard to reach…”

“Yeah and once you reach them, they are so hard to engage…”

“They don’t trust us.”

So if you manage to engage them, you can’t qualify them.”

“I’d settle for just a few answers to my questions. They stonewall. Or they don’t even know what they want.”

“And even if you manage to qualify them? Good luck closing them. Pack a lunch. Many lunches. They take forever to say yes.”

“Yeah, and there’s a second “yes,” have you noticed? They buy and then they never use what they bought. They never even break the seal!”

“And the moment the next thing catches their eye, they are gone. No loyalty.”

A collective sigh. Always a collective sigh around the room.

The bitch session was complete, and with eyes cast down, we proceeded to talk SMB lead gen.

One VP of Marketing said – never forget it – SMBs are the toughest sell on Planet Earth.

True that.

And there’s more than 30-million of them.

As fragmented as any Consumer market – maybe moreso. Self-described “snowflakes.”

“There is NO Small Business out there like mine!”

When you hear that 30-million times, you have to wonder what makes one florist so much different than another, but you still respect it.

You learn to embrace the fragmentation of your target market and you get to work, with the occasional visit from an outsider that gives permission to open up a fresh bitch session on the same reach-engage-qualify-close-keep agenda.

A Center of Gravity

Eight years ago, there was no center of gravity for those of us responsible for selling and serving Small Business customers at scale.

None.

When I met Peter Hutto in 2017, we bonded over our shared experience with bitch sessions, but he framed the bitch session in a way that cracked open my head.

“It’s crazy,” he said, “That all these people trying to sell to Small Businesses figure it out on their own time and their own dime.”

Peter’s framing defined for me, for the first time, a center of gravity.

A center of gravity for his work, my work, the people we were meeting, their work.

Really a recognition that there was no center of gravity.

How could all these smart people be struggling so universally, and in such isolation from each other?

More importantly, the framing prompted questions, variations on “Hey, do you ever talk to anyone about these challenges you bitch about?”

Nope. No, not at all.

So the question became obvious.

What if we got all these people in the same room all at once? And we let everybody bitch, and we let them realize they’re all bitching about the same things.

What happened next was… crazy.

Our ambition was hardly ambition: could we get a dozen or so leaders in this “space” of selling to SMBs in the same room, maybe at the Admirals Club in Chicago-O’Hare. Quick in, quick out.

Could we talk about how we find solutions to SMB reach and engagement and sales and service?

Could we frame that whole “own time, own dime” “center of gravity” argument and actually get anyone… to show up?

We started dialing.

And everyone picked up the phone.

Erik Day, the VP of SMB at Dell was literally the first.

Then Laura Goldberg, the CMO of Legal Zoom.

Peter brought Randy Parker, the Founder of Constant Contact.

I was introduced to Raj Mukherjee, the EVP/GM of Indeed.

Then Janet Shijns, the CMO of Office Depot. “I’m so in.”

Christal Bemont, the CRO of SAP/Concur.

Scott Gifis, the President of AdRoll. “Can I bring my team?”

Doug Llewellyn, the CEO of Purch/Business.com. “Do you take Sponsors?”

Jeff Perry of Docusign. Steven Handmaker of Assurance. Pete Steger of Kabbage.

Not only did every one of them have something to say (they understood the “framing” all too well.)

They wanted a stage to talk about it.

I had coined this combination of letters – B2SMB – and I was dubious about how effective it was. I honestly thought it took too long to explain – Business-to-Small-Business.

But during those first few phone calls, everybody got it.

More importantly, when I said that B2SMB was fundamentally different from B2B, a specialization, a genuine skillset and a different operating system (I was rolling) I was met with “Yeah. Yeah!”

And the center of gravity started to take shape.

October 3-4, 2017

The legendary investor, Howard Tullman, an early supporter of bizHive, offered us space inside of 1871, Chicago’s famous start-up incubator inside the Merchandise Mart for Day 1.

And it was there that over 100 of us squeezed into too-small a space to talk and listen about this profession that up to that moment didn’t have a name with people we up to that moment had not met.

It was very, very hard to get people to sit.

Not surprisingly, it was Erik Day of Dell who fixed everyone’s attention. He said something that froze the room: “I’ve taken 100% of my digital ad budget and directed it to SMB Influencers.”

I recall asking “What’s an Influencer?”

But the room had already erupted in questions.

The moment crystalized both the shared pain and the desperate need for new relief. Paid search had grown ridiculously expensive – what was the workaround? Everyone was experimenting. Erik had found something.

The “model” of peer wisdom was manifested.

Day 2 was more of the same, and our crowd grew to over 200.

Steven Aldrich, the CPO of GoDaddy back in 2017, told a story that still resonates.

It came from his early days at Intuit, re-tooling Quickbooks.

Steven’s small QB Dev team was in a windowless office space, like a basement skunk works. And besides the single door in and out, there was a green door on one wall that, for whatever the reason, no one really ever opened.

On the other side of that door was the Quickbooks Customer Service Team.

When the green door between Product Development and the “Room Where Customers Spoke” was opened, magic began to happen.

Steven’s team spent hours sitting right by their CSR counterparts, just listening.

Listening to the SMB, one at a time. Gaining insights. Recognizing patterns. Converging inputs not into a fragmented pile but into a cohesive vision that quite literally made the Quickbooks juggernaut.

The obvious answer – listen to the customer – just needed someone to open that green door.

We didn’t just hear from the Big Names. Howard had suggested 5 start-ups to attend, and we agreed to give each of them 3 minutes on stage to give their pitch. All had Small Business offerings.

3 stood out.

Brian Bar of Victory Lap, fresh from building the Groupon sales organization, he was offering scalable sales training for SMBs. Still going strong.

Nicole Wood of Ama la Vida, a career-coaching start-up, who asked the audience, “What does a Small Business look like? She looks like me.” Still going strong.

And Adam Johnson of Active Campaign. Yes. Right on the cusp of exploding in the unicorn success they enjoy to this day.

From those days forward, it was the people. There wasn’t even an “Institute” yet. But we had the people.

By the end of October, it was beyond clear: we needed to put a structure to the moment and all that we had discovered within it.

Without meaning to, we were transcribing the principles of building and selling products and services at scale to SMBs.

Those 40 leaders who took the stage in October of 2017, the 200+ attendees who listened, were not just bitching.

They were doing serious work.

They were encountering peers who were serious about their work of serving Small Business customers. They were treating each other seriously.

For most, it was a new feeling.

That was especially true for those from the very large companies whose offering to Small Business was a watered down version of their Enterprise offering.

Hutto, Aldrich and Sam Artmann (SVP of Web.com) tag-teamed the breakthrough of that first Summit, articulating a different discipline required to succeed with Small Business.

They planted flags:

-Small Business success requires different approaches in the total absence of Big Customer procurement.
-It requires different service in the absence of IT departments.
-It requires a different native curiosity in the absence of an RFP.
-It requires listening – especially between the lines – of what SMBs say.
-And a different patience. A whole new level of perseverance.

It requires – and still does – building for fragmentation while operating at scale.

This work has always been serious. And so were the professionals who carried out that work.

What was missing pre-2017?

Continuity.

Connectivity.

Collaboration.

A place where what was learned “on one’s own time and dime” could be saved, and shared and celebrated.

A place where those doing the work could multiply the effort together.

The Covid Years

At no time was our community more vital – and alive – than in early 2020, at the onset of Covid.

On March 21 of that Spring, I cancelled our 2020 Leaders’ Forum planned for Calistoga Springs.

I honestly thought we were done for.

But we were not. We doubled our Membership in 9 months, pushing our network past 3000.

Everyone wanted to talk to each other, and we were the forum for top-to-top exchanges, small group hangouts, and capacity-busting Wine Zooms.

Our virtual Leaders Forum in July of 2020 drew over 1000 attendees, and we had our greatest line-up of Speakers ever.

During that time, too, we built a permanent bridge from our world of B2SMB Enterprises to the world of SMB Advocacy Organizations. After all, we shared the same constituencies/customers – our precious Small Businesses.

By mid 2021, nineteen of the Top 25 Small Business Advocacy organizations were pro-bono Members of the Institute – from AEO and NAWBO to the National Hispanic Chamber of Commerce, Small Business Majority and the Kaufmann Foundation.

We aligned on a singular mission: to help SMBs not just survive the pandemic, but to thrive coming out of it.

Not only did B2SMB feel like a Profession. The Profession felt aligned, on a shared mission, and realizing its own continuity.

While not written, the Institute began to live its Principles.

Principles lived by its Members.

What Now Exists

Over the past eight years, the B2SMB profession has begun to see itself more clearly.

And you’ve helped the Institute see itself more clearly.

Through conversations. Through shared experience. Through continuity.

The B2SMB Institute did not create this profession.

It simply recognized it.

And by recognizing it, it helped create the conditions for its continuity.

Today, you ARE the Institute, serving as the lighthouse for the $2.5 trillion B2SMB market.

Not directing it.

Not controlling it.

But ensuring that you and your peers navigating it can see clearly.

What’s on our shared horizon?

You already know that your professions will be shaped by forces even more consequential than those of the past eight years. So will the Institute’s.

Artificial intelligence will reshape how Small Businesses are reached, served, and supported.

New companies will emerge. Existing companies will transform.

But the fundamental reality will remain:

Small Business will continue to be the most important AND most challenging customer in the global economy.

The leaders responsible for serving them will continue to require shared intelligence, shared continuity, and shared recognition.

The Institute exists to steward that continuity.

To ensure that what is learned is not lost.

To ensure that those doing the work can see themselves and each other clearly, as peers and partners and co-authors of this market’s future.

My personal stake grew from a somewhat naive moment: I often said B2SMBI’s origins felt like the movie Footloose, with Peter and I hosting a secret dance in a barn.

Eight years ago, this did not exist.

Today, it does.

And the work continues.

–The Partners Circle was born during Covid, when the instinct to connect proved stronger than the instinct to retreat. It has only deepened since and the numbers are beginning to show why. In a market where the cost of direct customer acquisition keeps climbing, B2SMB leaders who collaborate are outperforming those who go it alone. Not marginally. Meaningfully. The Partners Circle exists to make that collaboration systematic.
–Between the Lines and its companion podcast, Between2Bs are the only sources focused solely on B2SMB. There is no shortage of data, there’s a shortage of interpretation; no shortage of gurus, but a shortage of clarifiers; no shortage of patterns, but an absence of pattern recognition. Our content is built for decision makers. Not followers. Not views. But for leaders looking for clarity, for causation, and for the sometimes contrarian truth.

Eight years ago, we were a room. Then a newsletter. Then a Summit. Then a community. Then a network of Partners. The B2SMBI “product” has never stood still and neither has the market it serves.

Today B2SMBI moves fluidly across channels, with less friction and a wider aperture than at any point in our history.

More ways in. More ways to engage. More ways to belong.

Today we roll out:

-New monthly dues pricing
-New monthly billing options
-A new “cancel anytime policy”
-A new Membership tier for individuals
-And a new Membership tier for Start-ups.

The forces bearing down on the B2SMB market have never been stronger.

Acquisition channels collapsing, AI overwhelming, consolidation looming, fragmentation multiplying and isolation under relentless pressure mounting to figure it the fuck out.

Now more than ever, you need peer wisdom and shared playbooks. You need partners. You need top-to-top collaboration. You need serious connections.

That is what we have refined over 8 years to meet this moment.

With you. For you. Made by you.

Our network IS our value.

Peter. Erik. Laura. Steven. Raj. Cristal.

Eric Groves. Stephanie Gorski. Jill Nelson. Eric Spadafora. Mark Tina. Kush Shrivastava. David Patrick.

And so many more. You know who you are.

You are the Institute’s “Framers.”

You have not only framed your businesses, your careers, you’ve framed this B2SMB profession. This community.

You’ve framed its Principles. And you’ve framed the B2SMB Institute.

We’ve written these Principles down for the first time. They’re yours. Read them here.

One final thanks with some final thoughts for the occasion.

I offer all of this without nostalgia.

I present it as neither pitch nor pivot.

I don’t give it to you as a memorial, nor as a message.

Just “You made this.”

You made this.

Let’s build more.

Dave.

Question 2

UPDATED B2SMB Career Playbook

PART 1, SECTION I.A

I. State of the B2SMB Nation: Market Realities and Opportunities

A. The Economic Headwinds: Reading the Signal, Not Just the Noise

Since November 2025, the enterprise B2SMB landscape has absorbed a series of workforce reductions that, taken together, represent something qualitatively different from the correction cycle of 2023 and 2024. That earlier wave was largely an over-hiring hangover: companies that had gorged on cheap capital and pandemic-era growth finally trimming back to reality. Painful, but familiar. A market finding its level.

This wave is different. And it requires a different kind of reading.

What Has Actually Happened Since November 2025

The list of large B2SMB enterprises announcing layoffs since we first published this guide 3 months ago is not a short one.

Block, the parent company of Square and Cash App and one of the most recognized names in SMB commerce infrastructure, announced in late February 2026 that it was eliminating approximately 4,000 positions, roughly 40% of its total workforce. CEO Jack Dorsey framed the decision not as financial distress but as strategic inevitability. Advances in AI, he wrote to shareholders, have changed what it means to build and run a company. This was not an austerity measure. It was a declaration of a new operating model.

Block was not alone.

Amazon (AWS, Amazon Business) eliminated approximately 16,000 positions in January 2026, explicitly targeting management layers to redeploy capital into AI infrastructure and data centers.
Shopify made cuts to its Partnerships division in January 2026, following a November 2025 round described as removing layers that created complexity. Shopify now requires teams to justify why AI cannot do a job before requesting new headcount. That policy alone tells you something.
Salesforce reduced approximately 1,000 positions in February 2026, consolidating around its Agentforce AI platform and pulling back on customer support staffing.
Microsoft continued an extended phase of operational trimming through November 2025 and into 2026, shifting away from traditional research roles toward AI-driven capability models.
Bank of America signaled in January 2026 that it expects its workforce to shrink through the year, not through formal layoffs but by not replacing people who leave, as AI handles their former functions.

According to Challenger, Gray and Christmas, U.S. employers announced more than 71,000 layoffs in November 2025 alone, the highest for that month since 2022.

The downstream signal is worth watching as well. ADP’s December 2025 report showed that while large enterprises were cutting, the pullback hit small establishments hardest, a contraction of roughly 120,000 jobs among small businesses in November 2025. That number matters because it shows up directly in your customers’ confidence, their spending, and their willingness to invest in new solutions.

What This Wave Is Actually Telling You

The 2023 and 2024 layoffs were a correction. This is a restructuring. The distinction matters for your career.

A correction is cyclical. Headcount returns when the cycle turns. A restructuring is directional. The roles that are disappearing are not being held in reserve. They are being redesigned, automated, or eliminated in favor of smaller teams operating with greater AI leverage. The companies executing these cuts are not struggling. Block’s announcement was confident. Shopify’s policy is assertive. These organizations believe they are moving toward something, not away from something.

For B2SMB professionals, the honest takeaway is this: the organizations you have worked for, or have looked to as anchors of the industry, are actively reconsidering what kind of talent they need and in what volume. That is unsettling. You are entitled to feel it.

What Is Not Changing

The SMB market itself is not contracting. It is growing, at a rate of more than 550,000 new business formations per month in the United States. That number has held with remarkable consistency through every macro disruption of the past several years. The demand for tools, platforms, services, and expertise that helps small businesses operate, compete, and grow is not diminishing. It is expanding.

The large enterprises serving that market are getting smaller. But the market they serve is getting larger. That gap, between a consolidating supplier base and an expanding customer base, is precisely where your opportunity lives.

The Emerging 180, the cohort of rising B2SMB companies the Institute has been tracking across 30 sub-categories, are evidence of that gap being filled. New players are building, hiring, and positioning. They need people who understand this market in their bones: who can sell to, build for, and support small business customers at scale. That expertise is not being automated. It is, if anything, becoming more valuable as the large incumbents shed the organizational depth that used to carry it.

Key Takeaway: The layoff news is real and worth taking seriously. What it signals is structural change in how B2SMB companies are built and staffed, not a collapse of the market those companies serve. The professionals who will navigate this moment well are those who can read the difference between a shrinking employer landscape and a growing opportunity landscape. They are not the same thing.

What This Means for You

Do not anchor your confidence to the incumbents. The stability that once came from working at a recognized B2SMB enterprise is genuinely less reliable than it was three years ago. That is not a reason for panic. It is a reason to reposition.

Reposition toward the market’s durability, not any single player’s permanence. Build expertise that travels: in SMB customer behavior, in AI-augmented workflows, in the specific verticals where small businesses are forming and growing fastest. The professionals who understand why small businesses buy, how they adopt technology, and what makes them stay are going to be in demand regardless of which logo is on the door.

The ground has shifted. Your footing does not have to.

B. The SMB Resilience Factor: The Durability Advantage

New business formations in the United States have averaged more than 550,000 per month over the past two years, a pace that has held through inflation, rising rates, and now enterprise-scale restructuring.

This resilience stems from several factors:

Economic Diversification: Unlike enterprise clients who may operate in a single sector, the SMB market spans every industry imaginable. When one sector struggles (e.g., retail), others thrive (e.g., home services, healthcare).

Adaptability: Small businesses pivoted faster than larger organizations during the pandemic, and they’ve maintained that agility. They’re often early adopters of tools that provide immediate value.

Government Support Infrastructure: Programs like the SBA’s lending initiatives and various state-level support programs have provided a safety net that didn’t exist in previous economic downturns.

Key Takeaway: The SMB market isn’t just surviving. It’s evolving and growing, creating sustained demand for solutions that address their specific needs.

What This Means for You:

Reframe your career narrative around SMB resilience rather than enterprise stability. When interviewing or positioning yourself internally, emphasize your understanding of SMB durability and diversification. Companies serving this market need professionals who see SMBs not as “small enterprise” customers, but as a distinct, sustainable market with unique characteristics. Develop expertise in at least 2-3 SMB verticals (e.g., professional services, restaurants, healthcare practices) so you can speak credibly about their specific challenges and opportunities.

C. The Rise of the “Indie” SMB: The Solopreneur Economy

Perhaps the most significant trend reshaping B2SMB is the explosive growth of solopreneurs and micro-businesses (1-5 employees). The gig economy and remote work revolution have enabled millions to launch independent ventures, from freelance consultants to e-commerce operators to content creators. The current wave of enterprise layoffs, representing tens of thousands of experienced professionals now reconsidering their options, is accelerating that formation rate in real time.

This segment has distinct characteristics:

Technology-Native: Indie SMBs are typically founded by millennials and Gen Z entrepreneurs who expect software-based solutions and are comfortable with digital tools.

Value-Conscious: Without access to enterprise budgets, they scrutinize every subscription and demand clear ROI.

Community-Oriented: They actively participate in online communities, learn from peers, and make purchasing decisions based on recommendations from trusted networks.

DIY Until They Can’t: They’ll attempt to solve problems themselves until complexity or time constraints force them to seek help, and that’s where your opportunity lies.

Key Takeaway: The indie SMB represents the fastest-growing segment within the small business market, but they require fundamentally different engagement strategies than traditional SMBs with employees.

What This Means for You:

Position yourself as someone who understands the solopreneur mindset. This means:

Developing content marketing skills that speak to individual business owners, not procurement teams
Understanding community-led growth and how to engage in spaces like Reddit, Discord, and niche Facebook groups
Recognizing that “ease of use” and “time to value” aren’t just buzzwords. They’re make-or-break factors for this segment
Building expertise in self-service onboarding and product-led growth strategies

If you’re in sales, learn to identify and nurture these customers differently. If you’re in product, advocate for features that reduce friction for solo users. If you’re in marketing, master the art of peer-to-peer influence and user-generated content.

II. The AI Revolution in B2SMB: Threat or Your Greatest Ally?

A. AI as a Job Enhancer, Not a Replacement

The narrative around AI and jobs has been dominated by anxiety, but the reality for B2SMB professionals is far more nuanced. That distinction requires a sharper argument now than it did a year ago, when the layoff news was about over-hiring. Today companies are cutting specifically because AI has made fewer people sufficient. The nuance is not whether AI is displacing work. It is whether it is displacing yours. Recent research suggests that AI tools are augmenting rather than replacing knowledge workers, with professionals who actively incorporate AI into their workflows reporting productivity gains of 20-40%.

In the B2SMB context specifically, AI excels at handling the repetitive, time-consuming tasks that have long plagued go-to-market teams:

For Sales Professionals:

AI-powered prospecting tools can analyze thousands of potential SMB customers to identify those most likely to convert
Conversation intelligence platforms can analyze sales calls and provide real-time coaching
Automated CRM data entry eliminates hours of administrative work weekly

For Marketing Teams:

AI content generation tools can create first drafts of SMB-focused content at scale
Predictive analytics can optimize ad spend across SMB segments
Personalization engines can customize website experiences for different SMB verticals

For Product Developers:

AI can analyze customer support tickets and user behavior to identify friction points
Machine learning models can predict which SMB customers are at risk of churning
Natural language processing can synthesize feedback from thousands of small business users

Key Takeaway: The professionals who will thrive are those who view AI as a co-pilot that handles routine tasks, freeing them to focus on strategic thinking, relationship-building, and creative problem-solving. These are areas where human judgment remains irreplaceable.

What This Means for You:

Start incorporating AI tools into your daily workflow immediately. Not next quarter, not when your company mandates it, but now. Experiment with ChatGPT for drafting customer emails, Claude for analyzing competitor positioning, Jasper for marketing copy, or Gong for sales insights. Document your productivity gains and be prepared to articulate specifically how AI has made you more effective. In your next performance review or job interview, you want to be the candidate who can say: “I increased my output by 30% by using AI for X, which allowed me to spend more time on high-value activity Y.”

B. Must-Have AI Skills for Your Resume

The job market is rapidly bifurcating into two groups: professionals who actively leverage AI and those who don’t. To position yourself in the former category, develop these specific competencies:

1. Prompt Engineering for Business Applications

This isn’t about becoming a technical expert. It’s about knowing how to extract maximum value from AI tools for B2SMB use cases. Can you craft prompts that generate SMB-specific marketing personas? Can you use AI to simulate customer objections for sales training?

2. AI-Augmented Research and Analysis

Learn to use AI tools to synthesize market intelligence, analyze competitor strategies, and identify emerging trends in SMB verticals. Tools like Perplexity AI, Claude, and specialized research assistants can compress hours of research into minutes.

3. Workflow Automation with AI

Understanding how to build AI-powered workflows using platforms like Zapier, Make.com, or native AI features in tools like HubSpot and Salesforce. For SMB-focused professionals, this often means creating scalable processes that can serve hundreds or thousands of small customers efficiently.

4. AI Tool Evaluation

Developing the ability to assess which AI tools are genuinely valuable for SMB customers versus which are overhyped. This is increasingly important as SMB decision-makers look to their vendors for guidance on AI adoption.

5. Ethical AI Usage and Data Privacy

Understanding the limitations and risks of AI, particularly around data privacy. This is a critical concern when dealing with small business customers who may not have sophisticated data governance.

Key Takeaway: AI literacy is no longer optional. It’s a baseline requirement for B2SMB professionals, similar to how digital literacy became non-negotiable in the 2000s.

What This Means for You:

Create an “AI Skills” section on your LinkedIn profile and resume. Be specific: don’t just say “experienced with AI tools.” Say “use Claude and ChatGPT to reduce customer research time by 40%” or “implemented AI-powered lead scoring that improved SMB conversion rates by 25%.” Consider pursuing micro-credentials like:

Google’s AI Essentials certificate
HubSpot’s AI for Marketers certification
LinkedIn Learning’s “AI for Sales” courses

More importantly, build a portfolio of AI-enhanced work examples. If you’re in marketing, show before-and-after examples of AI-improved campaigns. If you’re in sales, document how you used AI to shorten your sales cycle. Make the value tangible and specific.

C. The Emerging AI Service Gap: Beyond the Product

Here’s the uncomfortable truth that most B2SMB SaaS companies are just beginning to confront: selling AI features to small businesses is relatively easy, but helping them actually implement and derive value from those features is exponentially harder. And that’s where the enormous career opportunity lies.

Recent surveys of small business owners reveal that while 60-70% express interest in AI tools, fewer than 20% have successfully integrated AI into their daily operations. The gap between purchase and productive use represents a massive opportunity.

Why SMBs Struggle with AI Implementation:

Lack of Technical Expertise: Small business owners are experts in their craft (plumbing, accounting, retail), not in configuring AI tools.
Time Poverty: They’re running the business day-to-day and lack bandwidth for tool setup and optimization.
Integration Complexity: AI tools rarely work in isolation. They need to connect with existing systems, which requires technical knowledge most SMBs don’t have.
Change Management: Even simple AI tools require workflow changes, and SMBs often lack the organizational capacity to manage that transition.

The “Implementation Gap” Opportunity:

Forward-thinking B2SMB companies are beginning to recognize that their competitive advantage doesn’t lie in having the best AI features. It lies in ensuring customers actually use them successfully. This is creating demand for professionals who can:

Conduct workflow audits to identify where AI can provide the most value
Provide hands-on implementation support beyond typical onboarding
Create industry-specific AI templates and playbooks
Offer ongoing optimization and training services
Build integrations between AI tools and customers’ existing tech stacks

Key Takeaway: The next wave of B2SMB career opportunities won’t be in building or selling AI tools. It will be in the implementation, integration, and ongoing support that bridges the gap between purchase and value realization.

What This Means for You:

Start positioning yourself as an “AI implementation specialist” rather than just a marketer, salesperson, or product manager. This means:

Build Technical Competency: You don’t need to become a developer, but you should understand APIs, webhooks, and basic integration concepts. Take courses on platforms like Coursera or Udemy on “APIs for Non-Programmers” or “Introduction to Integration Platforms.”

Develop a Service Mindset: Study how agencies and consultancies structure their engagements. Read case studies on successful AI implementations. Learn to think in terms of “implementation sprints” and “value realization timelines.”

Create Implementation Frameworks: Develop your own repeatable processes for helping SMBs adopt AI tools. Document these frameworks and showcase them in your portfolio or during interviews.

Target the Right Companies: When job hunting, prioritize B2SMB companies that are moving beyond product-only offerings to include services, support, and “done-for-you” solutions. These companies will value your implementation expertise far more than traditional product-first organizations.

III. Actionable Steps for Immediate Career Enhancement

A. “Intrapreneurship”: Innovating from Within

While the job market remains competitive, one of the most effective career strategies is making yourself indispensable in your current role by driving innovation and measurable impact. This “intrapreneurial” approach not only increases your job security but also builds a compelling case study for future opportunities.

How to Become an Intrapreneur in the B2SMB Space:

1. Identify a High-Value Problem

Look for inefficiencies or opportunities that directly impact SMB customer satisfaction, retention, or acquisition. Examples:

“Our onboarding process loses 40% of SMB customers in the first 30 days”
“We have no systematic way to gather and act on feedback from micro-business customers”
“Our sales team spends 60% of their time on administrative tasks instead of selling”

2. Propose a Solution with Clear ROI

Develop a specific, resourced proposal that shows how addressing this problem will impact the bottom line. Use data wherever possible:

“By implementing an AI-powered onboarding assistant, we can reduce time-to-value by 50% and improve 30-day retention by 15%, representing $X in preserved MRR”

3. Start Small and Build Proof Points

You don’t need executive approval to begin. Run a pilot with a subset of customers or within your team. Document results meticulously. Success at small scale gives you credibility to expand.

4. Evangelize and Scale

Once you have results, share them widely within your organization. Write internal case studies, present at company meetings, and create resources others can use to replicate your success.

Key Takeaway: Companies retain and promote people who solve meaningful problems without being asked and who can demonstrate measurable impact on business outcomes.

What This Means for You:

Schedule time this week to:

Identify 3 specific pain points in how your company serves SMB customers
Choose the one you’re best positioned to address
Create a one-page proposal outlining the problem, your proposed solution, required resources, and projected impact
Share it with your manager or relevant stakeholder

Even if your proposal isn’t immediately approved, you’ve demonstrated strategic thinking and initiative. Document this effort. It becomes a powerful interview story about your leadership and problem-solving abilities.

B. Upskilling for the Future: Strategic Learning Investments

Not all professional development is created equal. In a constrained job market, you need to be strategic about which skills you develop, focusing on those that are both in-demand and complementary to the B2SMB market’s evolution.

High-Value Micro-Credentials and Certifications:

For Marketing Professionals:

HubSpot’s Advanced Marketing Certifications (Free)
- Particularly valuable: Inbound Marketing, Content Marketing, and the newer AI for Marketers cert
- Why it matters: HubSpot dominates the SMB martech space; these certifications demonstrate platform expertise that’s immediately applicable
Google Analytics 4 Certification (Free)
- Critical as SMB websites and e-commerce platforms migrate to GA4
- Combines with your B2SMB knowledge to help small businesses understand their customer behavior
Meta Blueprint Certifications (Low cost)
- Essential for SMB social media marketing, where Facebook and Instagram remain dominant channels
- Focus on the “Small Business” specialty certifications

For Sales Professionals:

Sandler Training or Challenger Sales Certifications ($-$$)
- Methodologies that work particularly well in consultative SMB sales
- Widely recognized by B2SMB companies
MEDDPICC or Similar Sales Methodology (Free-$)
- Brings rigor to SMB sales processes, making you attractive to scaling B2SMB organizations
- Many free resources available online; paid certifications available through various providers
LinkedIn Sales Navigator Certifications (Free with Sales Navigator)
- Platform-specific but highly relevant given LinkedIn’s importance in B2SMB prospecting

For Product Professionals:

Product-Led Growth Micro-MBA (ProductLed.com) ($$)
- Essential for understanding how SMB products should be designed for self-service adoption
- Increasingly required knowledge for B2SMB product roles
Pragmatic Institute Certifications ($$-$$$)
- Industry-standard product management training with strong B2SMB applicability
- Consider starting with “Foundations” before moving to specialty certifications
Jobs-to-be-Done Certification (JTBD.info) ($)
- Framework that’s particularly powerful for understanding SMB customer needs
- Differentiates you from feature-focused product managers

For Customer Success Professionals:

Success Coaching Certified (SuccessCoaching.co) ($$)
- Focused specifically on SMB success strategies
- Created by industry leaders with deep B2SMB expertise
Gainsight Certification Programs (Free-$)
- Platform-specific but valuable as Gainsight gains traction in the B2SMB space

Cross-Functional Skills:

SQL for Data Analysis (DataCamp, Codecademy) ($)
- Ability to extract and analyze SMB customer data yourself is increasingly valuable
- Doesn’t require deep technical background
Basic APIs and Integration Knowledge (Zapier University, Make Academy) (Free)
- Critical for the AI implementation specialist role discussed earlier
- Makes you dramatically more valuable in SMB-focused organizations

Key Takeaway: Invest in credentials that combine immediate market demand with long-term relevance to B2SMB trends, particularly those related to product-led growth, AI implementation, and SMB-specific methodologies.

What This Means for You:

Create a 90-day upskilling plan:

Month 1: Choose one free certification most relevant to your current role and complete it. Update your LinkedIn profile immediately upon completion.

Month 2: Begin a paid certification or course that addresses your biggest skill gap relative to where you want your career to go (e.g., if you’re in marketing but want to move toward AI implementation consulting, start learning about APIs and integration platforms).

Month 3: Create a portfolio piece or case study that demonstrates your newly acquired skills. This might be:

A mock project showing how you’d implement AI for a specific SMB vertical
An analysis of a B2SMB company’s go-to-market strategy with recommendations
A sample onboarding playbook for SMB customers in a specific industry

Don’t wait for your employer to fund this development. View it as an investment in your career insurance. Given what is happening at the enterprise level right now, that insurance is not a metaphor.

Do tell your manager about your learning initiatives. Frame it as making yourself more valuable to your current organization while subtly signaling your ambition and forward-thinking approach.

Conclusion: Positioning Yourself for the New B2SMB Reality

The B2SMB landscape has fundamentally changed, but change creates opportunity for those who adapt quickly. The professionals who will thrive are those who:

Understand that SMB resilience creates a sustainable career foundation, even as individual companies and sectors fluctuate
Embrace AI as a force multiplier rather than a threat, actively developing AI literacy and integration skills
Recognize the implementation gap as the next frontier of B2SMB value creation and position themselves accordingly
Take ownership of their career development through intrapreneurship and strategic upskilling

The path forward isn’t about waiting for market conditions to improve or for your company to provide direction. It’s about proactively developing the skills, experience, and positioning that make you indispensable to B2SMB organizations today and essential to where the market is heading tomorrow.

In Part 2 of this series, we’ll dive into tactical job search strategies. We’ll cover how to revamp your professional brand, network strategically in the B2SMB ecosystem, and nail interviews by demonstrating deep SMB market expertise. Until then, begin implementing the actionable steps outlined above. Your future self will thank you.

About This Series

This is Part 1 of a three-part series on navigating the B2SMB career landscape in the age of AI and economic uncertainty. Future installments will cover modern job search strategies (Part 2) and future-proofing your career as an AI implementation specialist (Part 3).

PART 2: The Modern B2SMB Job Search: Standing Out in a Crowded Field

Q: What’s expected of me?

Expected is such a strong word, but here’s our advice. You are experiencing that rare occasion as a professional when no one is evaluating your performance or clipping your wings for sport. It ain’t often you are amongst peers who genuinely want to give and get help . Bring your curiosity, your candor, your humor and your you.

Q: Will I really meet people?

Let’s start at the fact that you will actually meet people – not just grab an obvious glance at their name-tag on the run. We intentionally keep the attendee list limited, so you can actually make genuine connections with everyone. You are amongst peers from a wide spectrum of brands (see 2024’s event page for clues.) We’re all naturally impressed with the fact that you love this B2SMB space as much as we do, and even more the SMBs that we serve. Lastly, many of our attendees have been here before – some for years – and they know how to welcome you. And if all else fails, submit to Dave’s “grab and deliver” with a “Hey, I gotta introduce you to ______.”

Q: How do I meet Attendees ahead of time?

First, try our LinkedIn Company Page , follow and scan our growing community there. Beginning mid-April, we’ll launch registration for our “Meet Your Fellow Forum-Goers” program, where you can choose the attending Brands you’d like to connect with and we’ll make a warm intro via e-mail on your behalf. But like Match.com, this service is opt-in for both parties. As we think everyone would want it. As attendees commit we will update almost daily what new brands are joining us.

Introduction

If you’re reading this, you’re likely in one of two situations: actively searching for your next B2SMB role, or strategically positioning yourself for when the right opportunity emerges. Either way, the traditional job search playbook (polish your resume, apply to dozens of positions, hope for callbacks) is increasingly ineffective in the competitive B2SMB landscape.

The reality is stark: quality B2SMB roles often receive 200+ applications within the first 48 hours of posting. Your resume might get 6 seconds of initial review time. And increasingly, you’re competing not just against other candidates, but against AI-powered applicant tracking systems designed to filter you out.

But here’s the good news: most candidates are still using outdated strategies. They’re applying to every vaguely relevant posting with generic materials, failing to differentiate themselves, and wondering why they’re not getting responses. This creates a massive opportunity for professionals who understand how to position themselves specifically for the B2SMB market.

This installment provides a tactical roadmap for distinguishing yourself in the B2SMB job market. From crafting materials that immediately signal your expertise, to networking strategically, to interviewing in ways that demonstrate you truly understand the small business customer.

I. Revamping Your Professional Brand for the B2SMB Niche

A. Beyond the Generic Resume: Becoming a B2SMB Specialist

Most professionals make a critical mistake: they create one “master resume” and send it everywhere with minimal customization. This approach virtually guarantees you’ll blend into the crowd. In the B2SMB space, you need materials that immediately communicate: “I’m not just a marketer/salesperson/product manager. I’m a B2SMB specialist.”

The Language of B2SMB Expertise

Keywords matter enormously, both for ATS systems and for human reviewers. Your resume and LinkedIn profile should incorporate B2SMB-specific terminology:

Replace Generic Terms:

“Customer acquisition” → “SMB customer acquisition” or “small business onboarding”
“Enterprise sales” → “B2SMB sales” or “small business sales at scale”
“Product development” → “SMB-focused product development” or “product-led growth for small businesses”

Include Specific SMB Indicators:

Average contract value (ACV) ranges you’ve worked with ($50-500/month is classic SMB)
Volume metrics (e.g., “managed portfolio of 500+ small business accounts”)
SMB-specific challenges you’ve solved (e.g., “reduced onboarding time for solopreneurs from 2 hours to 15 minutes”)
Relevant verticals (e.g., “specialized in dental practices, law firms, and accounting offices”)

Quantify Everything in SMB-Relevant Terms

Hiring managers for B2SMB roles care about different metrics than enterprise-focused positions. Structure your achievements accordingly:

Weak Example: “Increased customer satisfaction scores by 15%”

Strong Example: “Increased customer satisfaction scores among small business owners (sub-50 employees) by 15% through implementation of industry-specific onboarding playbooks, resulting in 22% improvement in 90-day retention”

Weak Example: “Led product development initiatives”

Strong Example: “Led development of self-service onboarding features that enabled 10,000+ solopreneurs to implement the platform without human support, reducing customer acquisition cost by 40%”

The SMB Success Story Framework

Every bullet point on your resume should ideally follow this structure:

Action: What you did
SMB Context: Who it affected (size of business, vertical, volume)
Method: How you did it (especially if it involved SMB-specific strategies)
Result: Quantified business impact

Example: “Redesigned email nurture campaign for newly-acquired micro-businesses (1-5 employees) using behavioral segmentation, resulting in 35% increase in feature adoption within first 30 days across 5,000+ customers”

Key Takeaway: Generic resumes get generic results. B2SMB-specific resumes that demonstrate deep understanding of small business economics, challenges, and buying behavior will immediately stand out to hiring managers who understand this market.

What This Means for You:

This week, conduct a resume audit:

Count how many times “SMB,” “small business,” “solopreneur,” or related terms appear in your resume. If it’s fewer than 5 times, you’re not clearly positioning yourself as a B2SMB specialist.
Review every bullet point and ask: “Does this communicate that I understand the unique challenges of serving small businesses at scale?” If not, rewrite it.
Add an “Areas of Expertise” section near the top of your resume that includes phrases like:
- “B2SMB Go-to-Market Strategy”
- “Small Business Customer Journey Optimization”
- “Product-Led Growth for SMB”
- “High-Volume, Low-Touch Sales Models”
- “Solopreneur & Micro-Business Segments”
Create role-specific versions of your resume. You should have at minimum three versions: one emphasizing SMB marketing expertise, one emphasizing sales/customer acquisition, and one emphasizing product/customer success. Each should have the same core achievements but framed differently.

LinkedIn Optimization

Your LinkedIn profile requires similar treatment, with a few additional considerations:

Headline Formula: Don’t: “Marketing Manager at Company X” Do: “B2SMB Marketing Leader | Helping SaaS Companies Acquire & Retain Small Business Customers | AI-Powered Growth Strategies”

About Section Structure:

First paragraph: Your B2SMB passion and expertise (written in first person, conversational)
Second paragraph: Specific SMB challenges you solve
Third paragraph: Notable achievements with SMB-relevant metrics
Fourth paragraph: Your approach/philosophy for serving small businesses
Final line: Clear call-to-action

Featured Section: Showcase B2SMB-specific work:

Case studies of SMB customer success
Articles you’ve written about serving small businesses
Presentations on B2SMB strategies
Portfolio samples of SMB-focused campaigns or products

B. Demonstrating Empathy for the SMB Owner

Understanding SMB economics intellectually is different from demonstrating genuine empathy for the small business owner’s lived experience. The latter is what truly differentiates exceptional B2SMB professionals, and it’s what hiring managers are screening for.

The SMB Owner’s Reality

Small business owners face pressures that are qualitatively different from enterprise executives:

Time Scarcity: According to research from the National Federation of Independent Business (NFIB), small business owners work an average of 50-60 hours per week, often handling multiple roles simultaneously. They’re not just the CEO. They’re also the CFO, HR manager, IT department, and janitor.

Key Takeaway: SMB owners don’t have time for your learning curve, lengthy implementation processes, or “strategic” initiatives that don’t show immediate value.

Financial Vulnerability: Unlike enterprise customers with departmental budgets, every subscription comes directly from the owner’s pocket (or business account, which feels the same). A $500/month tool that enterprises wouldn’t notice can represent a significant investment for a small business.

Key Takeaway: Price objections from SMB owners aren’t about negotiating. They’re about genuine financial pressure and ROI uncertainty. You need to demonstrate value in their language: hours saved, revenue generated, disasters prevented.

Impostor Syndrome and Learning Anxiety: Many small business owners aren’t “tech-savvy” and feel overwhelmed by complex software. They worry about looking incompetent in front of support reps or sales people.

Key Takeaway: Condescension is career-ending in B2SMB. You need to demonstrate patience, clear communication, and the ability to meet customers where they are technologically.

Demonstrating SMB Empathy in Your Materials

Your resume, LinkedIn, and portfolio should include specific evidence of SMB empathy:

Language Choices:

Use terms like “time-strapped business owners” not “unsophisticated users”
Reference “budget-conscious small businesses” not “price-sensitive customers”
Discuss “simplifying” and “streamlining” not “educating” or “training”

Story Selection: Include anecdotes that show you’ve walked in SMB owners’ shoes:

“Having worked in my family’s retail business, I understand firsthand the challenge of evaluating new technology while managing daily operations”
“Spent 30 days working alongside customers in their auto repair shops, dental offices, and restaurants to understand their actual workflows”

Problem Framing: When describing challenges you’ve solved, frame them from the SMB owner’s perspective:

Weak Framing: “Increased product adoption rates”

Strong Framing: “Recognized that busy restaurant owners didn’t have time to watch training videos, so redesigned onboarding as a 15-minute guided setup that could be completed during their slow afternoon hours”

What This Means for You:

Develop what I call your “SMB Empathy Statement,” a concise narrative that explains why you’re passionate about serving small businesses and demonstrates you understand their reality. This should be:

Personal: Connect to your own experience (family business, side hustle, consulting for SMBs)
Specific: Reference actual challenges you’ve observed, not generic platitudes
Outcome-focused: Explain how this empathy has made you more effective

Example: “I got into B2SMB marketing after watching my parents struggle to find affordable, usable technology for their HVAC business. They’d invest in ‘solutions’ that required IT departments they didn’t have, or support teams that treated them like they should already understand everything. That experience drives my obsession with creating marketing that speaks plainly, products that work out-of-the-box, and customer experiences that respect business owners’ time and expertise in their craft.”

Practice delivering this statement in 30 seconds, 60 seconds, and 2 minutes. You’ll use variations of it in cover letters, interviews, and networking conversations.

C. The Power of a Niche Portfolio

While enterprise-focused professionals can often succeed with a traditional resume alone, B2SMB specialists benefit enormously from a portfolio that demonstrates specific, relevant expertise. This is true across disciplines, not just for designers or marketers.

Portfolio Components by Role

For Marketers:

SMB Campaign Case Studies: Document 2-3 campaigns you’ve run targeting small businesses, including:
- Target audience definition (specific SMB segment)
- Channel strategy and rationale
- Creative samples (ads, landing pages, email sequences)
- Results with SMB-relevant metrics (cost per SMB customer acquired, activation rates, etc.)
Content Samples: Create a collection of SMB-focused content:
- Blog posts addressing common SMB challenges
- Email sequences for SMB customer nurture
- Social media campaigns for SMB audiences
- Video scripts or webinar outlines for small business owners
Competitive Analysis: Analyze 3-5 B2SMB companies’ marketing strategies, identifying what works, what doesn’t, and opportunities you see. This demonstrates your analytical skills and market knowledge.

For Sales Professionals:

SMB Sales Playbook: Create a sample playbook showing your methodology:
- Ideal customer profile for a hypothetical B2SMB product
- Prospecting strategies for high-volume SMB sales
- Email and call scripts tailored to small business owners
- Objection handling specific to SMB concerns (price, time, complexity)
- Sample proposal or ROI calculator
Sales Performance Dashboard: Create a visual showing your typical metrics:
- Volume of SMB accounts managed
- Average deal size and sales cycle
- Conversion rates at each stage
- Customer acquisition cost vs. lifetime value
Customer Success Stories: Written case studies (anonymized if necessary) showing how you’ve helped specific SMB customers succeed, focusing on the relationship-building and problem-solving aspects.

For Product Professionals:

SMB Product Teardowns: Analyze 3-5 successful B2SMB products:
- What makes them work for small businesses
- Onboarding flow analysis
- Feature prioritization for SMB vs. enterprise needs
- Areas for improvement
Product Specs/PRDs: Create sample product requirement documents for SMB-focused features:
- Problem statement from SMB perspective
- User stories for solopreneurs and small teams
- Success metrics relevant to SMB customers
- Go-to-market considerations
Design Mockups: Even if you’re not a designer, create basic wireframes or sketches showing how you’d solve a common SMB product challenge (simplified onboarding, better mobile experience, etc.).

For Customer Success/Support:

Onboarding Playbooks: Develop industry-specific onboarding guides:
- “First 30 Days: Getting Started for Dental Practices”
- “Quick Start Guide for Solopreneurs”
- Include timeline, key milestones, success criteria
Support Content Library: Create help center articles, video tutorials, or knowledge base content addressing common SMB questions in clear, non-technical language
Health Score Framework: Design a customer health scoring system specifically for SMB customers, including the unique indicators that predict SMB churn or expansion

Portfolio Presentation Best Practices

Platform Options:

Personal Website: Most professional; use tools like Webflow, Squarespace, or Notion (which now has public pages)
Notion Portfolio: Quick and clean; great for text-heavy case studies
Google Sites: Free and simple; perfectly adequate for most purposes
LinkedIn Featured Section: For shorter pieces that you want maximum visibility

Structure:

Include a brief “About” section emphasizing your B2SMB expertise
Make your best piece the first thing visitors see
Include context for each project (even if hypothetical): what problem you were solving, who the target SMB customer was, what your role was, what the outcome was
Use plenty of visuals (screenshots, mockups, data visualizations)
Make everything downloadable as PDFs

Key Takeaway: In a competitive job market, showing beats telling. A portfolio that demonstrates specific B2SMB expertise eliminates doubt and distinguishes you from candidates who only have a resume.

What This Means for You:

Your 30-day portfolio build plan:

Week 1: Choose your portfolio platform and create the basic structure. Write your “About” section emphasizing B2SMB expertise.

Week 2: Document one existing project from your work history, reframing it with SMB-specific context and results. Anonymize as needed.

Week 3: Create one hypothetical/spec project if you lack sufficient real examples. Choose a real B2SMB company and create something they don’t currently have (a campaign, playbook, product feature, etc.).

Week 4: Add one thought leadership piece, an article analyzing a B2SMB trend, strategy guide, or perspective on where the market is heading.

Share your portfolio link in your LinkedIn profile, email signature, and at the top of your resume. When applying to jobs, mention it in your cover letter: “I’ve compiled several B2SMB case studies that demonstrate my approach. You can view them at [link].”

II. Networking in the New Era: Quality over Quantity

The old networking advice (attend every event, collect every business card, connect with everyone on LinkedIn) was never great, but it’s especially ineffective in today’s job market. With the rise of remote work, the dissolution of many in-person networking events, and the sheer noise on platforms like LinkedIn, you need a more strategic approach.

A. Identifying the “Right” Companies: Looking Beyond the Big Names

Many B2SMB professionals instinctively gravitate toward household names like HubSpot, Intuit, Salesforce, Shopify. While these are excellent companies, they’re also extraordinarily competitive to break into, and their massive scale can mean less opportunity for individual impact and career growth. And, as recent restructurings at Shopify and Salesforce demonstrate, less structurally stable than their brand recognition implies.

Meanwhile, hundreds of smaller, rapidly-growing B2SMB companies are actively hiring. Companies that offer more responsibility, faster career progression, and often better work-life balance.

The “Hidden” B2SMB Job Market

According to data from industry analysts, the B2SMB software market includes thousands of companies beyond the major brands. These include:

Vertical SaaS Players: Companies building software for specific SMB industries:

Healthcare: Tebra, Weave, Solutionreach (dental/medical practices)
Legal: Clio, MyCase, PracticePanther (law firms)
Construction: Buildertrend, CoConstruct, Procore (contractors)
Food Service: Toast, Square for Restaurants, TouchBistro
Professional Services: Honeybook, Dubsado, 17hats (photographers, consultants, etc.)

Key Takeaway: Vertical SaaS companies often have deep SMB expertise and strong economics because they solve specific problems for defined markets. They also tend to value candidates with vertical-specific knowledge.

Horizontal SMB Platforms with Focus: Companies that serve SMBs across industries but with specific functional focuses:

Accounting/Bookkeeping: QuickBooks, Xero, FreshBooks, Wave
HR/Payroll: Gusto, Rippling, Justworks
Payment Processing: Stripe, Square, PayPal
E-commerce: Shopify, BigCommerce, WooCommerce, Squarespace
Marketing: Mailchimp, Constant Contact, ActiveCampaign

Emerging B2SMB Categories: Watch for newer categories where early-stage companies are gaining traction:

AI implementation services for SMBs
SMB-focused fintech (lending, banking, financial management)
Workflow automation tools designed for non-technical users
Industry-specific marketplaces connecting SMBs with customers

How to Identify High-Potential B2SMB Companies

Look for these indicators:

Growth Signals:
- Recent funding announcements (Series A through C are often ideal stages)
- Expansion hiring (opening multiple roles simultaneously)
- Geographic expansion or new product launches
- Positive reviews on G2, Capterra focused on SMB users
SMB-First Indicators:
- Pricing pages showing sub-$500/month plans
- Case studies featuring small businesses, not just enterprises
- Marketing content addressing small business owner challenges
- Self-service signup options (product-led growth model)
Cultural Fit Signals:
- Leadership with SMB backgrounds (founders who ran small businesses or worked at known B2SMB companies)
- Employee reviews on Glassdoor mentioning customer-centricity
- Public content showing empathy for SMB customers

Research Tools and Resources

Crunchbase: Track funding, hiring, and news about B2SMB companies
LinkedIn: Follow companies, monitor who they’re hiring, and see where people in your network work
G2/Capterra/Software Advice: Browse SMB software categories to discover companies
SaaS-focused newsletters: SaaStr, SaaS Weekly, The Hustle cover B2SMB companies
Vertical-specific publications: Follow trade publications for industries you want to serve (e.g., Dental Economics, Restaurant Business, Accounting Today)

Key Takeaway: The best opportunities are often at companies you’ve never heard of. Smaller, focused B2SMB players where you can make significant impact and where competition for roles is less intense.

What This Means for You:

Create your B2SMB target company list:

Identify 3-5 SMB verticals you’re interested in serving (based on personal interest, prior experience, or market potential)
Research 20-30 companies that serve those verticals or the broader SMB market
Tier them:
- Tier 1: Dream companies where you have connections or warm leads
- Tier 2: Strong companies where you’ll need to network your way in
- Tier 3: Backup options or companies to monitor
Follow all target companies on LinkedIn and set up Google Alerts for their names
Identify 3-5 people at each Tier 1 company you want to connect with (more on this in the next section)

Update this list monthly as you learn more and as companies evolve. The goal isn’t to apply to every opening at every company. It’s to be strategic and focused.

B. The Informational Interview is Not Dead: Strategic Relationship Building

Conventional wisdom says informational interviews are outdated, that busy professionals won’t make time for them, and that they rarely lead to jobs. This conventional wisdom is wrong, or at least incomplete.

The truth is that poorly executed informational interviews are useless. But strategic, thoughtful relationship-building conversations remain one of the most effective ways to access unadvertised opportunities and get referrals into competitive roles.

Why Informational Interviews Still Work in B2SMB

The B2SMB community is relatively tight-knit. People who’ve worked in this space tend to know each other, move between companies, and value recommendations from trusted colleagues. According to hiring data, 30-50% of B2SMB roles are filled through referrals rather than direct applications.

More importantly, B2SMB professionals generally care deeply about helping others succeed in serving small businesses. There’s a missionary quality to the best people in this space. They’re often willing to talk to people who demonstrate genuine interest and preparation.

The Modern Informational Interview Framework

Forget the old “I’m doing career research” approach. Instead, use what I call the “Mutual Value Exchange” method:

Step 1: Identify the Right People

Don’t reach out to random people at target companies. Be specific:

Recent hires in roles similar to what you want (they just went through the hiring process)
People who’ve written articles or shared insights on LinkedIn about B2SMB topics
Second-degree connections where you have a mutual connection who can introduce you
Alumni from your college or people from your previous companies
People who’ve recently spoken on podcasts or at conferences about B2SMB

Step 2: Craft a Compelling Outreach Message

Your initial message (LinkedIn or email) should:

Be specific about why you’re reaching out to them specifically
Reference something they’ve created or shared (article, post, podcast appearance)
Offer value or demonstrate shared interest before asking for anything
Make a small, specific ask (15-minute call, not “pick your brain”)

Weak Outreach Example: “Hi, I’m looking for a job in B2SMB marketing. I saw you work at [Company]. Would you have time to chat about your experience?”

Strong Outreach Example: “Hi [Name], I just read your LinkedIn post about the challenges of marketing to solopreneurs vs. traditional SMBs. The point about attention scarcity really resonated. I’ve been focused on B2SMB marketing for 5 years, most recently at [Company] where we serve micro-businesses, and I’m researching companies that are innovating in this space. Would you be open to a 15-minute call? I’d love to hear about [Company’s] approach to [specific challenge they’ve mentioned or that you’ve observed], and I’m happy to share what’s worked in my experience as well.”

Step 3: Prepare Strategically

Before the conversation:

Research the person thoroughly: LinkedIn, company blog, social media
Research their company: recent product launches, customer reviews, competitive positioning
Prepare 5-7 specific questions that show you’ve done homework
Prepare 2-3 insights or examples you can share that might be valuable to them

Step 4: Structure the Conversation

The ideal 15-20 minute informational interview:

Minutes 1-2: Thank them, explain your background briefly (30 seconds), and reiterate why you wanted to talk to them specifically
Minutes 3-12: Ask your prepared questions, listen actively, and look for opportunities to share relevant insights from your experience
Minutes 13-17: Ask about their path into B2SMB and what advice they’d give
Minutes 18-20: Ask if there’s anyone else they’d recommend you talk to, and how you can be helpful to them

Excellent Questions to Ask:

“What do you think most B2SMB companies get wrong about [specific challenge]?”
“How has your approach to [X] evolved as you’ve learned more about serving small businesses?”
“What surprised you most about working with SMB customers vs. other segments?”
“What skills or experiences do you think will be most valuable in B2SMB over the next 2-3 years?”
“Are there any trends you’re seeing in how SMBs are adopting [technology/strategy]?”

Step 5: Follow Up Strategically

Within 24 hours:

Send a thank-you note that references specific insights from the conversation
Share something valuable: an article, resource, or introduction that relates to your conversation
Connect on LinkedIn with a personalized note

Over time:

Stay in touch periodically (every 6-8 weeks) by sharing relevant content or updates
Make introductions when you can help them
Let them know when you apply to their company (if appropriate) or when something from your conversation proves useful

Key Takeaway: Informational interviews work when you approach them as relationship-building and knowledge exchange, not as thinly-veiled job requests. The goal is to build genuine connections with people in the B2SMB space who can provide insight, advice, and eventually, referrals or opportunities.

What This Means for You:

Start your networking campaign this week:

Identify 10 people from your target company list who fit the profile above
Craft 3-5 different outreach templates customized for different scenarios (alumni, mutual connection, content creator, etc.)
Send 3 outreach messages this week, then 3 more each subsequent week
Track everything in a simple spreadsheet: who you reached out to, when, their response, conversation date, follow-up actions
Set a goal of 2 informational interviews per week once you get into a rhythm

Remember: these conversations are valuable even if they don’t directly lead to job opportunities. You’re building market knowledge, refining your positioning, and creating a network that will serve your entire career.

C. Engaging in B2SMB Communities: Building Visibility and Authority

While one-on-one networking is powerful, community participation allows you to build relationships with multiple people simultaneously and establish yourself as a knowledgeable voice in the B2SMB space.

Where B2SMB Professionals Congregate

LinkedIn Groups and Hashtags:

Search for groups like “B2SMB Marketing,” “Small Business Software,” “SaaS for SMB”
Follow hashtags: #B2SMB, #SMBMarketing, #SMBSales, #ProductLedGrowth
Engage consistently: comment thoughtfully on posts, share insights, ask questions

Key Takeaway: LinkedIn engagement is less about posting constantly and more about being consistently valuable in conversations. Quality comments on others’ posts often drive more visibility than your own posts.

Specialized Communities:

SaaStr Community: Events, forums, and resources focused on B2B/B2SMB SaaS
Product-Led Alliance: Community for product-led growth (PLG) professionals, highly relevant for B2SMB
Pavilion (formerly Revenue Collective): Membership community for GTM leaders, including B2SMB track
Growth.org: Community focused on growth strategies, strong B2SMB presence
Online Geniuses: Slack communities for marketers, including B2SMB focus groups

Industry-Specific Communities: If you’re targeting specific SMB verticals, join their trade communities:

Dental/Medical: Dental Economics, Physicians Practice communities
Legal: ABA groups, legal tech forums
Restaurant/Hospitality: Restaurant owner Facebook groups, industry Reddit threads
Professional Services: Industry-specific associations (photographers, consultants, etc.)

Reddit and Other Forums:

r/smallbusiness: 1M+ members; great for understanding SMB owner perspectives
r/entrepreneur: Startup and small business focus
r/marketing, r/sales: Large communities with SMB-relevant discussions
Industry-specific subreddits for verticals you’re targeting

Strategy for Effective Community Engagement

The 5-3-1 Rule:

For every 5 pieces of content you consume (read, watch, listen)
Comment thoughtfully on 3
Create 1 original post or contribution

This ratio keeps you learning and engaged without burning out on content creation.

High-Value Contribution Types:

Thoughtful Responses: Answer questions with specific, actionable advice based on your experience. Always add context: “When I was at [Company] serving [type of SMB], we faced this exact challenge. Here’s what worked…”
Contrarian Perspectives: Politely challenge conventional wisdom when you have evidence it doesn’t work for SMBs: “I see this advice often, but in my experience working with 500+ small businesses, it rarely works because [specific reason]…”
Resource Sharing: Share useful tools, articles, or frameworks with brief context on why they’re valuable for B2SMB professionals
Case Studies and Stories: Share specific (anonymized if needed) examples of B2SMB challenges you’ve solved
Questions That Spark Discussion: Ask questions that invite others to share their expertise: “For those working with solopreneurs, what’s been your most effective onboarding strategy?”

Building Visibility Without Being Salesy

The goal of community engagement isn’t to promote yourself obviously. It’s to demonstrate expertise consistently so that when people need someone with your skills, you’re top of mind.

Do:

Share specific, actionable insights
Acknowledge others’ contributions
Ask for help when you genuinely need it
Celebrate others’ successes
Be generous with introductions and resources

Don’t:

Constantly mention that you’re job searching
Turn every conversation toward yourself
Pitch your services or promote your portfolio unsolicited
Engage only when you need something

Key Takeaway: Community engagement is a long game. Consistent, valuable participation over 3-6 months builds reputation and relationships that often surface opportunities organically.

What This Means for You:

Launch your community engagement strategy:

Join 3-5 communities this week: 2 general B2SMB communities and 2-3 specific to your discipline or target vertical
Spend 30 minutes daily reading and commenting in these communities (use your coffee break or commute time)
Set a goal of 5 meaningful comments per week to start, scaling to 10-15 as you get comfortable
Create one original post monthly: share a case study, ask a thoughtful question, or offer a perspective on a B2SMB trend
Track connections made: When you have valuable exchanges with people, connect on LinkedIn and note how you met

Remember: people hire people they know, like, and trust. Community engagement is how you build all three in a scalable way.

III. Nailing the B2SMB Interview

You’ve secured an interview at a promising B2SMB company. Now comes the critical part: demonstrating that you don’t just understand B2SMB intellectually, you live and breathe it. Here’s how to stand out in interviews by showing authentic expertise and passion for serving small businesses.

A. Answering the “Why B2SMB?” Question

This question (or variations like “Why are you interested in serving small businesses?” or “What draws you to this market?”) comes up in virtually every B2SMB interview. It’s often one of the first questions, and it’s more important than most candidates realize.

Hiring managers ask this because they’ve hired people who viewed B2SMB as a stepping stone to “real” enterprise work, who didn’t respect SMB customers, or who burned out because they didn’t understand the unique challenges of the segment. They’re screening for genuine commitment and empathy.

What NOT to Say

Avoid these common weak responses:

“I think it’s a growing market” (too generic, could apply to any segment)
“I’ve always wanted to work at [Company]” (doesn’t explain why B2SMB specifically)
“Enterprise sales cycles are too long” (negative framing)
“Small businesses need help” (sounds condescending, implies SMB owners are helpless)

The Framework for a Strong Answer

Your “Why B2SMB?” response should include three elements:

1. Personal Connection: A specific, authentic reason you care about small businesses 2. Professional Insight: Evidence that you understand what makes this market unique 3. Career Commitment: Signals that this isn’t a temporary stop

Strong Example for Someone With Family Business Background:

“I grew up watching my parents run their landscaping business, 10 employees, serving residential and small commercial clients. I saw how much they poured into it, how every hiring decision mattered, how choosing the wrong software vendor could cost them thousands and weeks of productivity. When I got into marketing, I initially worked in enterprise, but I kept thinking about businesses like my parents’. Companies that create most of the jobs in this country but often get treated like second-class customers by the tech industry.

Over the past four years at [Current Company], I’ve focused exclusively on B2SMB marketing, and what I love is the immediacy of impact. When we help a small business owner save five hours a week or increase their revenue by 20%, we’re changing their life, not just moving a metric. I also love the creativity required. You can’t throw massive budgets at problems; you have to be smart, empathetic, and efficient. That’s the kind of marketing I want to do for my whole career.”

Strong Example for Someone Without Family Business Background:

“My path to B2SMB actually started when I was freelancing during grad school. I was doing marketing consulting for local businesses, a dental practice, a gym, a financial advisor, and I became fascinated by how different their needs were from the enterprise clients I’d read about in case studies. These owners weren’t looking for enterprise-scale solutions; they needed tools that worked immediately, didn’t require IT support, and had clear ROI.

When I joined [Current Company], I specifically chose an SMB-focused role because I’d seen firsthand how poorly most vendors serve this market. There’s this gap between what small businesses need and what the tech industry offers them, and I want to spend my career bridging that gap. What excites me about B2SMB is that you have to deeply understand your customers’ reality, not just their business challenges, but their daily lives, to serve them well. That combination of empathy and strategy is what makes this market intellectually fascinating and personally fulfilling for me.”

Key Takeaway: The best “Why B2SMB?” answers demonstrate that you’ve chosen this market deliberately, understand its unique characteristics, and have evidence of your commitment to serving small businesses well.

What This Means for You:

Write out your “Why B2SMB?” answer this week:

Identify your authentic connection to small businesses (family business, side hustle, consulting, passion for entrepreneurship, etc.)
Articulate what you’ve learned that makes B2SMB distinct from other markets
Connect it to your career goals: explain why you want to continue in this space
Practice delivering it in 60-90 seconds until it sounds natural, not rehearsed
Prepare a 30-second version for networking conversations and a 2-3 minute version for formal interviews

Record yourself giving this answer and watch it back. Does it sound authentic and passionate? If not, revise until it does.

B. The “Toughest Sell on Planet Earth”: Preparing for SMB Sales and Marketing Challenges

B2SMB professionals have a saying: “SMBs are the toughest sell on planet Earth.” Interviewers often want to know if you understand why, and more importantly, if you have strategies for overcoming these challenges.

Why B2SMB is Uniquely Challenging

The Budget Reality: Small businesses typically operate on tight margins, with limited discretionary spending for new tools or services. According to small business research, the average SMB uses 40-60 different software tools but constantly evaluates whether each one is worth the cost.

Key Takeaway: In B2SMB, you’re not competing against other vendors. You’re competing against the business owner deciding to hire another employee, purchase inventory, or invest in equipment instead of your solution.

The Decision-Maker Paradox: You’re often selling directly to the business owner (good: one decision-maker, short chain), but that owner is also the person doing the work (bad: they’re time-strapped and hard to reach, and implementation burden falls on them).

Key Takeaway: Traditional B2B sales strategies that assume you’re selling to someone who will delegate implementation to others don’t work in B2SMB.

The Trust Gap: Small business owners have often been burned by vendors who overpromised, provided poor support after the sale, or sold them tools they couldn’t use. They’re skeptical and need substantial proof before committing.

Key Takeaway: Building trust is slower in B2SMB, but once you have it, loyalty can be incredibly strong. The challenge is surviving long enough to build that trust at scale.

How to Address These Challenges in Interviews

When asked about B2SMB sales or marketing challenges, structure your answer using the “Challenge-Strategy-Example” framework:

For Sales Professionals:

“One of the biggest challenges in B2SMB sales is the decision-maker paradox I mentioned. You’re selling to someone who has to be convinced AND has to do the implementation themselves AND is constantly interrupted by their actual business.

My strategy has been to make the buying process mirror the experience they’ll have as a customer, low friction, high value, respectful of their time.

First, I focus prospecting on businesses showing buying signals (searching for solutions, asking questions in communities, experiencing the problem acutely) rather than cold outreach, because SMB owners don’t have time for discovery calls about problems they’re not actively trying to solve.

Second, I use async communication heavily. Video messages showing ROI, calculators they can use on their own time, case studies from their specific industry, so they can evaluate our solution when it works for them, not when I’m available.

Third, I sell outcomes, not features. SMB owners don’t care that we have AI-powered analytics; they care that they’ll be able to identify their most profitable customers without hiring a data analyst.

For example, at [Previous Company], I was selling to restaurant owners, some of the busiest, most time-strapped SMB owners you can find. I created a 3-minute video that showed exactly how our product would help them reduce food waste and increase margins, with specific dollar figures for a restaurant their size. Then I followed up with a one-click ROI calculator customized to their type of restaurant. That approach took my response rate from 15% to 40% because I was making it easy for them to see the value without requiring them to take time out of running their restaurant.”

For Marketing Professionals:

“The biggest B2SMB marketing challenge is what I call ‘the attention-trust-budget triangle.’ SMB owners have no attention for your marketing, no inherent trust in vendors, and no budget for experimentation.

My approach is to focus on education-based marketing that delivers immediate value before asking for anything. At [Current Company], I created industry-specific guides. ‘The Complete Guide to Hiring for Auto Repair Shops,’ ‘The Contractor’s Guide to Managing Seasonal Cash Flow,’ things that solved pressing problems for our target SMBs. These weren’t gated; we gave them away freely.

The result was that we became a trusted resource before we were a vendor. When these business owners were ready to solve the problems our product addressed, we were already top-of-mind as the experts. This strategy took longer to show ROI than performance marketing, but the customers we acquired this way had 60% higher retention and were much more likely to advocate for us in their networks.

I’ve also learned that SMB marketing has to be omnichannel because you need to reach owners where they actually are, and that’s rarely on LinkedIn. For HVAC contractors, we found them on contractor forums and YouTube. For dentists, it was Facebook groups and industry publications. You have to go to them; they won’t come to you.”

For Product Professionals:

“The core B2SMB product challenge is balancing simplicity with power. Small businesses need tools that work immediately without configuration, but they also need solutions that can grow with them. Over-simplify and you lose them when they scale; over-complicate and they never adopt.

At [Previous Company], we faced this when expanding from solopreneurs to businesses with 5-10 employees. Solopreneurs loved our simplicity; small teams needed collaboration features. We solved this by making the core experience remain simple. You could still use the product productively on day one with zero configuration, but we added a ‘Team’ layer that was entirely optional and discoverable over time, not forced during onboarding.

We also learned to design for interrupted workflows. SMB owners rarely complete multi-step processes in one session because they’re constantly being pulled back into their business. Every feature we built had to support ‘save and resume later,’ and we sent strategic reminder emails at natural resume points. That increased our task completion rate by 45%.”

Key Takeaway: Strong answers to challenge questions demonstrate that you understand the difficulties and have developed specific, proven strategies to overcome them. Generic answers about “working harder” or “being persistent” signal lack of real B2SMB experience.

What This Means for You:

Prepare 3-4 “challenge stories” this week:

Identify the top challenges relevant to your role (sales: long cycles and price objections; marketing: attention and trust; product: simplicity vs. power; CS: activation and expansion)
For each challenge, document:
- Why this is particularly acute in B2SMB
- The specific strategy you’ve used to address it
- A concrete example with metrics
Practice telling these stories in 2-3 minutes each
Prepare follow-up details in case they want to go deeper

Also prepare a thoughtful question about how the company you’re interviewing with approaches these challenges. It shows you’re thinking strategically about whether their approach aligns with your experience.

C. Asking the Right Questions: Evaluating Employer Commitment to SMB

Interviews are bidirectional. You should be evaluating whether the company truly understands and is committed to the SMB market. Many companies claim to serve small businesses but actually treat SMB as an afterthought to enterprise, lack authentic SMB expertise in leadership, or are pursuing unsustainable strategies.

Red Flags to Watch For

During your interview process, be alert for these warning signs:

1. Product-Market Fit Issues:

Customer reviews showing high churn or dissatisfaction
Pricing that’s clearly too high for most SMBs ($500+/month for simple tools)
Onboarding processes that require technical expertise or lengthy setup
No self-service option; everything requires sales calls

2. Cultural Signals:

Leadership team with no SMB experience (all come from enterprise backgrounds)
Marketing that talks about features, not outcomes
Case studies that feature only the largest customers
Customer support that’s clearly understaffed or only available during business hours (when SMB owners are busiest)

3. Strategic Misalignment:

Company trying to move upmarket to enterprise while still claiming SMB focus
No clear differentiation from competitors
Rapid executive turnover or sudden large-scale workforce reductions, especially in customer-facing roles.
Unrealistic growth expectations that suggest desperation

Smart Questions to Ask

Ask these questions to assess the company’s true commitment to and understanding of SMB:

For All Roles:

“Can you walk me through your typical customer journey, from first touchpoint to becoming a successful, retained customer?”
- Listen for: understanding of SMB buying behavior, realistic expectations for time-to-value, evidence of customer empathy
- Red flag: vague answers or overemphasis on the sale with little discussion of post-sale success
“What percentage of your customers would you consider ‘highly successful’ with your product, and what defines success?”
- Listen for: honest assessment, outcome-focused definition of success, acknowledgment of challenges
- Red flag: exaggerated success rates, feature-adoption-based definitions rather than customer-outcome-based
“What’s your biggest challenge serving SMB customers right now, and how are you addressing it?”
- Listen for: specific, honest challenge and concrete strategy to address it
- Red flag: “we don’t really have challenges” or vague, generic answers
“How does leadership here think about the trade-off between moving upmarket to larger customers versus deepening your SMB focus?”
- Listen for: clear strategy, understanding of the implications of each approach
- Red flag: signs they’re actually moving away from SMB despite the job posting

For Sales Roles:

“What’s your average customer acquisition cost, and how does that compare to customer lifetime value? How does that vary by customer segment?”
- Listen for: sustainable unit economics, understanding of different SMB segments
- Red flag: unwillingness to share, unsustainable ratios, or no segmentation
“What does your sales team’s relationship with customer success look like after the handoff?”
- Listen for: collaborative relationship, shared accountability for customer outcomes
- Red flag: complete handoff with no ongoing connection or accountability

For Marketing Roles:

“How do you balance demand generation with education and thought leadership for SMB audiences?”
- Listen for: sophisticated understanding of trust-building with SMB audiences
- Red flag: purely transactional, performance-marketing-only approach
“Can you share an example of marketing content that performed particularly well with SMB audiences and why you think it resonated?”
- Listen for: specific example, deep understanding of what makes SMB audiences tick
- Red flag: can’t provide examples or gives enterprise-focused examples

For Product Roles:

“How do you gather and prioritize feedback from SMB customers, and can you give me an example of a feature that came directly from SMB customer feedback?”
- Listen for: systematic feedback processes, evidence that they actually listen to and build for SMB
- Red flag: no clear process or examples, or examples that are clearly enterprise-driven
“What’s your philosophy on product-led growth vs. sales-led growth for SMB?”
- Listen for: thoughtful position aligned with customer needs and company strategy
- Red flag: religious adherence to one model without considering customer segment needs

For Customer Success/Support Roles:

“What does your team structure look like for supporting SMB customers? How is it different from enterprise support?”
- Listen for: dedicated SMB support strategy, understanding that SMB customers have different needs
- Red flag: one-size-fits-all support model
“What are your top drivers of churn, and what are you doing to address them?”
- Listen for: honest assessment, active initiatives to reduce churn
- Red flag: defensiveness or blaming customers (“they weren’t a good fit”)

Reading the Room

Pay attention to how interviewers respond to your questions:

Good sign: Thoughtful, specific answers; willingness to acknowledge challenges; asking follow-up questions about your experience
Warning sign: Defensive reactions; vague, marketing-speak answers; dismissiveness toward SMB challenges; inability to provide specific examples

Key Takeaway: The questions you ask signal your sophistication and help you avoid joining a company that’s not genuinely committed to or equipped for B2SMB success.

What This Means for You:

Before each interview:

Research the company’s SMB commitment:
- Read 20-30 recent customer reviews on G2/Capterra
- Analyze their pricing and positioning
- Review leadership backgrounds on LinkedIn
- Sign up for their product trial if available
Prepare 5-7 questions from the list above that are most relevant to your role and concerns
Bring a notebook and take notes on answers. It shows you’re serious and helps you evaluate later
After the interview, evaluate:
- Did their answers demonstrate deep SMB understanding?
- Were they honest about challenges?
- Do you believe they’re committed to SMB long-term?
- Would you be proud to represent this product to SMB customers?

If you get red flags, trust your instincts. A job that looks good on paper but is at a company that doesn’t truly understand or respect SMB customers will be frustrating and likely short-lived.

Conclusion: Your Strategic Job Search Action Plan

Landing the right B2SMB role in today’s competitive market requires a fundamentally different approach than the traditional “spray and pray” job search. Success comes from strategic positioning, targeted networking, and demonstrating authentic expertise in serving small businesses.

Your 30-Day Action Plan

Week 1: Positioning

Audit and rewrite your resume with B2SMB-specific language and metrics
Optimize your LinkedIn profile for B2SMB search
Begin building your portfolio with at least one case study or project

Week 2: Research and Targeting

Create your target company list (20-30 companies across tiers)
Research each company’s SMB commitment and culture
Identify 3-5 people at each Tier 1 company for outreach
Join 3-5 relevant online communities

Week 3: Networking Launch

Send first round of informational interview outreach (5-10 people)
Begin engaging in online communities (5 meaningful comments)
Attend or watch recordings of B2SMB-relevant webinars or events
Complete one professional development course or certification

Week 4: Interview Preparation

Write and practice your “Why B2SMB?” answer
Prepare 3-4 challenge/strategy stories with specific examples
Develop your list of smart questions for employers
Apply to 5-10 highly-targeted roles at your Tier 1 companies

Ongoing (Monthly):

Send 10-15 new networking outreach messages
Complete 4-8 informational interviews
Apply to 10-20 targeted roles (quality over quantity)
Create 1 new portfolio piece or publish 1 thought leadership article
Engage consistently in communities (15-20 comments/week)
Complete 1 micro-credential or course

Measuring Success

Track these metrics to ensure your job search is progressing:

Response rate to networking outreach (target: 30-40%)
Informational interviews conducted (target: 8-12 per month)
Interview conversion rate (applications to first interviews: target: 10-15%)
Quality of opportunities (are you getting interviews at companies you’re excited about?)

The Mindset Shift

Remember: in a competitive market, you’re not just looking for any job. You’re building a B2SMB career. Every networking conversation, every portfolio piece, every community interaction is an investment in your long-term positioning as a B2SMB expert.

The professionals who succeed aren’t necessarily the most qualified. They’re the ones who most effectively communicate their expertise, build genuine relationships, and demonstrate authentic commitment to helping small businesses thrive.

In Part 3 of this series, we’ll look ahead to the future of B2SMB careers, exploring how the AI implementation gap creates unprecedented opportunities for professionals who position themselves as strategic partners helping small businesses successfully adopt and leverage AI. We’ll cover emerging roles, skill development pathways, and how to future-proof your B2SMB career in an AI-centric world.

Until then, start implementing the strategies outlined above. Your next great B2SMB opportunity is out there, and now you have the roadmap to find it and win it.

About This Series

This is Part 2 of a three-part series on navigating the B2SMB career landscape in the age of AI and economic uncertainty. Part 1 covered the current market landscape and immediate career enhancement strategies. Part 3 will explore future-proofing your career as an AI implementation specialist in the B2SMB space.

Part 3: Future-Proofing Your B2SMB Career: The Rise of the AI Integrator

Introduction

We stand at an inflection point in the B2SMB market. Over the past 2 years, virtually every software vendor serving small businesses has added “AI-powered” to their feature lists. Sales and marketing teams tout machine learning capabilities, intelligent automation, and predictive analytics. Small business owners are being told that AI will revolutionize their operations, save them countless hours, and give them enterprise-level capabilities at SMB prices.

There’s just one problem: the vast majority of small businesses have no idea how to actually use these AI features effectively. They’re paying for capabilities they can’t implement, sitting through demos of features they can’t configure, and feeling increasingly overwhelmed by the gap between what’s promised and what they can realistically achieve.

This gap represents the most significant career opportunity in B2SMB since the shift to cloud computing. The next wave of successful B2SMB professionals won’t be those who build or sell AI tools. It will be those who bridge the implementation chasm, helping small businesses actually realize value from the AI capabilities they’re purchasing.

This final installment explores how to position yourself for this emerging opportunity, whether as an employee of a forward-thinking B2SMB company, an independent consultant, or an entrepreneurial service provider. We’ll examine the new roles being created, the skills you need to develop, and the practical steps to become what I call an “AI Integrator” for the SMB market.

I. The New Value Proposition: From Vendor to Partner

A. The AI Implementation Chasm: Why SMBs Can’t Do This Alone

The statistics are sobering. According to recent small business surveys, while approximately 70% of SMB owners express interest in using AI tools to improve their businesses, fewer than 20% have successfully implemented AI in any meaningful way. Among those who have adopted AI tools, a significant percentage report that they’re using only a fraction of the available capabilities.

This isn’t because small business owners are technophobic or resistant to innovation. The challenges they face are structural and deeply rooted in the realities of running a small business.

The Time Poverty Problem

Small business owners work an average of 50-60 hours per week according to NFIB research, often handling multiple roles simultaneously. They’re the CEO, CFO, head of sales, and sometimes the person taking out the trash. The idea that they have time to watch tutorial videos, experiment with AI prompts, integrate systems, and optimize workflows is fundamentally disconnected from their reality.

Consider a typical scenario: A dental practice purchases practice management software with AI-powered patient communication features. To implement it effectively, the practice owner would need to:

Analyze their current patient communication workflows
Configure the AI to match their practice’s tone and policies
Integrate it with their existing scheduling and billing systems
Train staff on how to use and monitor the AI
Continuously optimize based on patient responses
Troubleshoot when things go wrong

Even if each task is “simple,” the cumulative time investment is prohibitive for someone who’s also managing a dental practice, treating patients, and handling the business side of operations.

Key Takeaway: Time poverty isn’t just about being busy. It’s about cognitive load and decision fatigue. Every new tool, no matter how “easy,” adds complexity to an already overwhelming operational environment.

The Technical Expertise Gap

The AI tools marketed to SMBs often require more technical sophistication than vendors acknowledge. Setting up automation workflows, connecting APIs, writing effective prompts, interpreting analytics, and troubleshooting integration issues all require knowledge that most small business owners simply don’t possess.

This is compounded by the fact that AI tools often work best when integrated with multiple systems. A restaurant owner might want to use AI for inventory management, but that AI needs to pull data from their POS system, supplier ordering platform, and accounting software. Creating and maintaining those integrations requires technical skills far beyond what’s reasonable to expect from someone whose expertise is running a restaurant.

Research from various technology adoption studies shows that technical complexity is consistently cited as the primary barrier to SMB technology adoption, even above cost concerns.

Key Takeaway: The “no-code” revolution has made many things easier, but “easier” is not the same as “easy.” What seems simple to a tech-savvy professional can still be insurmountably complex for a time-strapped business owner.

The Strategy and Optimization Challenge

Perhaps the most underestimated challenge is that effectively implementing AI requires strategic thinking about workflows, priorities, and change management. It’s not enough to turn on a feature. You need to:

Identify which problems AI can actually solve versus which require human judgment
Redesign workflows to accommodate AI-generated outputs
Establish quality control processes
Train team members on new procedures
Monitor results and continuously optimize

A small accounting firm might purchase AI-powered document analysis software, but getting value from it requires rethinking their entire client onboarding process, deciding which document types to process automatically versus manually, training staff on reviewing AI outputs, and iterating based on accuracy rates.

This level of strategic implementation is beyond what most SMB owners can manage without guidance, not because they’re not smart enough, but because they lack the combination of time, technical knowledge, and implementation experience.

Key Takeaway: AI implementation isn’t just a technical challenge or a time challenge. It’s a strategy and change management challenge that requires expertise most SMBs don’t have in-house.

What This Means for You:

The implementation chasm creates three distinct career opportunities:

Employee Opportunity: B2SMB companies that recognize this gap are creating new roles focused on customer implementation and success with AI features. These roles combine elements of customer success, technical support, and strategic consulting.
Consulting Opportunity: Independent consultants who can help SMBs successfully implement AI are in increasingly high demand, with the ability to charge premium rates for their expertise.
Entrepreneurial Opportunity: There’s a growing market for “done-for-you” AI implementation services, either as standalone businesses or as service layers added to existing consulting or agency practices.

Start positioning yourself now by developing a point of view on AI implementation challenges in your target SMB verticals. Write about these challenges, discuss them in communities, and begin building case studies of successful implementations. The professionals who establish themselves as AI implementation experts over the next 12-24 months will have extraordinary career leverage.

B. The “Done-For-You” and “Done-With-You” Models: New Service Paradigms

The traditional B2SMB model has been product-centric: sell software, provide basic onboarding, offer technical support when things break, and hope customers figure out how to derive value. This model is increasingly inadequate in an AI-enabled world.

Forward-thinking B2SMB companies are shifting toward service-augmented models that recognize implementation support as a competitive differentiator and revenue opportunity. Two models are emerging as particularly effective for AI implementation.

The “Done-For-You” Model

In this model, the vendor or consultant takes full responsibility for implementing AI capabilities on behalf of the customer. The SMB owner specifies their goals and provides necessary access, but the implementation team handles everything else.

Example Scenarios:

Marketing Agency with AI Services: A marketing agency serving law firms might offer a “Done-For-You AI Content System” where they:

Analyze the law firm’s existing content and brand voice
Set up and configure AI content generation tools
Create custom prompts and templates specific to legal content
Establish quality control workflows
Train a designated firm staff member on basic maintenance
Provide ongoing optimization as part of a monthly retainer

The law firm gets the benefits of AI-powered content creation without needing to become AI experts themselves.

B2SMB SaaS Company: A project management platform serving construction contractors might offer a “Done-For-You AI Setup” premium onboarding package where they:

Conduct a workflow audit to understand how the contractor currently manages projects
Configure AI-powered project templates based on the contractor’s typical job types
Set up automated client communications using AI
Create custom reports and dashboards
Integrate with the contractor’s existing estimating and accounting software
Provide three months of weekly check-ins to optimize and troubleshoot

The contractor gets a fully configured, AI-enhanced system without spending dozens of hours on setup.

Value Proposition: SMBs are willing to pay significant premiums for done-for-you services because they eliminate risk, save enormous time, and deliver faster time-to-value. This model also creates stickier customer relationships and additional revenue streams for service providers.

Key Takeaway: Done-for-you AI implementation services can command 2-5x the price of software-only offerings while simultaneously improving customer satisfaction and retention.

The “Done-With-You” Model

This hybrid approach involves the vendor or consultant working collaboratively with the SMB to implement AI capabilities. Rather than taking complete control, the expert guides the business owner through the process, providing expertise, templates, and support while building the owner’s capability over time.

Example Scenarios:

Fractional AI Consultant: A consultant working with professional services firms might offer a 90-day “Done-With-You AI Implementation Program” that includes:

Initial assessment and strategy session to identify high-value AI use cases
Bi-weekly implementation sessions where consultant and owner work together to set up and configure tools
Custom templates and prompts developed collaboratively
Training on prompt engineering and AI tool optimization
Ongoing Slack or email support for troubleshooting
Final session on maintaining and scaling AI systems independently

The professional services firm develops internal capability while benefiting from expert guidance.

B2SMB Platform: A CRM company serving real estate agents might offer a “Done-With-You AI Adoption Track” as part of their customer success program:

Monthly group training sessions on AI features
Weekly office hours where customers can get live help implementing specific AI capabilities
A library of industry-specific AI prompt templates and workflows
A community where customers share AI implementation strategies
Quarterly 1-on-1 strategy sessions with an AI success specialist

Real estate agents learn to leverage AI while having expert support when they get stuck.

Value Proposition: Done-with-you models transfer knowledge to the customer while providing the scaffolding and support they need to succeed. This approach often results in better long-term adoption because customers develop genuine competency rather than complete dependence.

Key Takeaway: Done-with-you services balance the need for expert guidance with the reality that SMBs benefit from developing internal capabilities. This model is often ideal for customers who want to learn but recognize they need structured support.

Hybrid and Tiered Approaches

Many successful implementations combine both models, offering different service tiers:

Basic Tier: Software only with self-service resources (traditional model)

Growth Tier: Software plus done-with-you support (group training, office hours, templates)

Premium Tier: Software plus done-for-you implementation (full-service setup and optimization)

This tiered approach allows SMBs to choose the level of support that matches their budget, technical capability, and time availability while giving the vendor multiple revenue streams and expansion opportunities.

What This Means for You:

If you’re currently in a B2SMB role, advocate within your organization for moving toward service-augmented models. Present the business case:

Higher customer lifetime value through premium service tiers
Improved retention as customers successfully adopt AI features
Differentiation from competitors still offering software-only
Revenue diversification beyond pure software subscriptions

If you’re considering independent consulting or entrepreneurship, develop packages that incorporate these models. Start by offering done-with-you services (lower risk, easier to deliver) and expand to done-for-you as you build processes and potentially add team members.

Begin testing these concepts now, even informally. Offer to help a few customers implement AI features beyond your normal scope of work. Document the process, track the results, and develop repeatable methodologies. These case studies will become the foundation of your service offerings.

C. Case Study: The AI Implementation Specialist Role

To make this concrete, let’s examine how one professional successfully pivoted into an AI implementation specialist role at a B2SMB SaaS company.

Background: Sarah Chen’s Journey

Sarah spent five years as a Customer Success Manager at a marketing automation platform serving small professional services firms (accountants, lawyers, consultants). She managed a portfolio of 200+ customers, helping them with onboarding, adoption, and renewal.

When her company began adding AI features in early 2024, Sarah noticed a troubling pattern. Customers were excited about AI during sales demos, but adoption of AI features was below 15% even six months after launch. Those who did try the features often gave up quickly, citing confusion about how to use them effectively.

Sarah saw an opportunity. She began spending extra time with a subset of her customers, helping them not just turn on AI features but actually implement them strategically. She documented her approach and the dramatically improved outcomes.

The Pivot

Sarah proposed a new role to her leadership team: AI Implementation Specialist. She presented data showing that customers who received her hands-on AI implementation support had:

85% AI feature adoption (versus 15% company average)
40% higher retention rates
60% more likely to expand to higher-tier plans
Significantly higher NPS scores

The company created the new role for Sarah with three primary responsibilities:

High-Touch AI Implementation: Working directly with new and existing customers to implement AI features through a structured 90-day program
Playbook Development: Creating industry-specific AI implementation playbooks that other team members could use
Internal Training: Teaching sales, marketing, and other CS team members how to position and support AI features effectively

The Approach

Sarah’s implementation methodology involved:

Week 1-2: Discovery and Strategy

Audit customer’s current marketing workflows
Identify 2-3 high-value AI use cases specific to their business
Create custom implementation roadmap with clear milestones

Week 3-6: Hands-On Implementation

Weekly 60-minute working sessions via screen share
Configure AI features together, customizing for customer’s needs
Develop custom prompt libraries for their specific use cases
Set up quality control processes
Create simple documentation for their team

Week 7-10: Optimization and Transfer

Bi-weekly check-ins to refine and optimize
Address challenges and troubleshoot issues
Train additional team members if needed
Develop plan for independent operation

Week 11-12: Independence and Handoff

Final optimization session
Transition to standard CS support
Schedule 90-day follow-up check-in

The Results

Within 12 months, Sarah’s success led the company to hire a team of four AI Implementation Specialists. The program became a competitive differentiator mentioned prominently in marketing materials and a significant driver of customer satisfaction and retention.

Sarah herself was promoted to Director of AI Customer Success, overseeing the team and setting strategy for AI adoption across the customer base. Her compensation increased by 45%, and she became a sought-after speaker at B2SMB conferences on the topic of AI implementation.

Key Takeaways from Sarah’s Story:

She identified a gap: Rather than accepting low AI adoption as inevitable, she recognized it as a solvable problem and a career opportunity.
She tested her hypothesis: Before proposing a new role, she experimented with a small group of customers to prove the approach worked.
She presented data: Her proposal was backed by concrete metrics showing business impact, making it easy for leadership to approve.
She created systems: Rather than keeping her expertise as tribal knowledge, she documented playbooks that scaled beyond her individual capacity.
She positioned herself as indispensable: By combining customer empathy, technical capability, and strategic thinking, she created a role that was difficult to replace.

What This Means for You:

You don’t need to wait for your company to create an AI implementation role. Start by:

Identifying AI adoption challenges in your current customer base or target market
Volunteering to help a small number of customers implement AI features more deeply than your current role requires
Documenting your process and results meticulously
Building a business case for why your company should invest in AI implementation support
Proposing a pilot program either as an expansion of your current role or as a new role entirely

If your current company isn’t receptive, your documented success becomes a powerful case study for your next role at a more forward-thinking B2SMB company or as an independent consultant.

II. Emerging Roles and Skill Sets for the AI-Centric B2SMB World

The AI implementation opportunity is creating entirely new roles and significantly evolving existing ones. Understanding these emerging positions and the skills they require is essential for positioning yourself for the future of B2SMB.

A. The AI Implementation Consultant: Strategic Workflow Design

The AI Implementation Consultant role sits at the intersection of business strategy, technical capability, and customer success. Unlike traditional consultants who provide advice and recommendations, AI Implementation Consultants get hands-on, working directly with SMB customers to deploy, configure, and optimize AI tools for their specific needs.

Core Responsibilities:

Workflow Analysis and Design: The consultant begins by deeply understanding how the SMB currently operates. For a dental practice, this might mean mapping out patient communication workflows, appointment scheduling processes, and billing procedures. The goal is identifying where AI can provide meaningful value without disrupting what already works well.

Tool Selection and Configuration: Many SMBs are overwhelmed by the number of AI tools available. The consultant helps evaluate options based on the business’s specific needs, budget, and technical capacity, then handles the configuration to match the business’s requirements.

Integration Architecture: AI tools rarely work in isolation. The consultant designs and implements integrations between AI platforms and the SMB’s existing systems (CRM, accounting software, communication tools, etc.), ensuring data flows smoothly and reducing manual work.

Prompt Engineering and Customization: Generic AI outputs rarely work well for specific businesses. The consultant develops custom prompts, templates, and configurations that align with the business’s brand voice, industry requirements, and specific use cases.

Training and Knowledge Transfer: The consultant trains the SMB team on using AI effectively, creating documentation, and establishing processes for ongoing optimization. The goal is building capability, not creating dependence.

Ongoing Optimization: Initial implementation is just the beginning. The consultant monitors performance, gathers feedback, and continuously refines AI systems to improve results over time.

Required Skills:

Technical Skills (but not engineering-level):

Understanding of APIs, webhooks, and integration platforms (Zapier, Make, etc.)
Prompt engineering across multiple AI platforms (ChatGPT, Claude, Gemini, industry-specific AI)
Data analysis and ability to interpret AI performance metrics
Familiarity with common SMB software ecosystems (QuickBooks, Salesforce, HubSpot, Square, etc.)
Basic understanding of data privacy and security best practices

Business Strategy Skills:

Process mapping and workflow design
ROI analysis and business case development
Change management and adoption strategies
Industry-specific knowledge for target verticals
Project management and implementation methodologies

Soft Skills:

Exceptional ability to explain technical concepts in plain language
Patience and empathy for non-technical clients
Strong teaching and training capabilities
Problem-solving mindset and troubleshooting skills
Ability to manage client expectations realistically

Career Path and Compensation:

AI Implementation Consultants are commanding premium rates, both as employees and as independent consultants:

Employee path: Starting salaries for AI Implementation Consultants at B2SMB companies typically range from $75,000-$95,000, with senior roles reaching $120,000-$150,000 plus bonuses tied to customer success metrics.

Independent consultant path: Hourly rates range from $150-$300 depending on specialization and experience, with many consultants offering fixed-price implementation packages ranging from $5,000-$25,000 depending on scope.

The most successful consultants often specialize in specific SMB verticals (healthcare, legal, construction, etc.) where they can develop deep expertise and repeatable methodologies, commanding higher rates and achieving better results.

Key Takeaway: The AI Implementation Consultant role requires a unique combination of technical capability, business acumen, and teaching ability. It’s not pure technical work, nor is it pure strategy work. It’s hands-on implementation with strategic thinking.

What This Means for You:

To position yourself for AI Implementation Consultant roles:

Build technical foundations (next 3 months):

Complete courses on APIs and integration platforms (Zapier Academy is free and excellent)
Practice prompt engineering across multiple AI platforms
Learn to connect AI tools to common SMB software
Build 2-3 sample integration projects for your portfolio

Develop vertical expertise (next 6 months):

Choose 1-2 SMB verticals to specialize in
Study their specific workflows, pain points, and regulatory requirements
Build relationships with SMBs in these verticals
Create vertical-specific AI implementation frameworks

Create proof of expertise (ongoing):

Document every AI implementation you work on as a case study
Write articles or create videos about AI implementation challenges and solutions
Speak at industry events or in online communities
Build a portfolio site showcasing your implementation methodology

B. The SMB Success Manager 2.0: Proactive AI Strategy and Optimization

The traditional Customer Success Manager role is evolving dramatically in B2SMB companies. Where CSMs previously focused primarily on adoption, renewals, and reactive support, the SMB Success Manager 2.0 role is becoming proactive, strategic, and deeply focused on helping customers leverage AI to achieve business outcomes.

How the Role is Evolving:

From Reactive to Proactive: Traditional CSMs responded to customer issues and conducted quarterly business reviews. SMB Success Managers 2.0 proactively identify opportunities for customers to leverage new AI capabilities, reaching out with specific, actionable recommendations rather than waiting for customers to ask for help.

From Feature Adoption to Business Outcomes: Instead of tracking whether customers use specific features, the evolved role focuses on the business results customers are achieving. For a restaurant using a reservation platform, the focus shifts from “are you using AI-powered table management” to “has AI helped you improve table turnover and reduce no-shows?”

From Generalist to AI Strategist: SMB Success Managers 2.0 develop deep expertise in AI capabilities and maintain current knowledge of emerging AI tools and techniques. They become trusted advisors who can guide customers through the rapidly evolving AI landscape.

Core Responsibilities:

AI Capability Assessment: Regularly evaluating which AI features and capabilities would provide the most value for each customer based on their business model, challenges, and maturity level.

Strategic Planning: Working with customers to develop AI adoption roadmaps that align with their business goals, showing them a path from basic implementation to advanced optimization.

Hands-On Enablement: Going beyond training to actually work alongside customers in implementing and optimizing AI features, similar to the implementation consultant role but as an ongoing relationship rather than a project-based engagement.

Performance Monitoring: Tracking AI-related metrics for customers (time saved, revenue impact, efficiency gains) and using this data to demonstrate value and identify optimization opportunities.

AI Change Management: Helping SMB owners manage the organizational change that comes with AI adoption, including training team members, updating processes, and addressing resistance or concerns.

Expansion and Upsell: Identifying opportunities for customers to expand their use of AI features or upgrade to higher-tier plans as they derive more value and need more advanced capabilities.

Required Skills:

Many of the skills overlap with the AI Implementation Consultant role, but with some differences in emphasis:

Technical Skills:

Strong understanding of the company’s AI features and how they work
Ability to troubleshoot common AI implementation issues
Familiarity with data analysis and reporting
Basic prompt engineering and AI optimization

Strategic Skills:

Business acumen and understanding of SMB economics
Ability to identify and quantify business impact of AI adoption
Roadmap development and prioritization
Vertical-specific industry knowledge

Relationship Skills:

Long-term relationship building and account management
Consultative approach to customer success
Ability to have difficult conversations about underutilization or value realization
Cross-functional collaboration with sales, product, and support teams

Career Path and Compensation:

The SMB Success Manager 2.0 role typically pays $70,000-$110,000 for individual contributors, with senior positions and team lead roles reaching $120,000-$160,000. Many companies are adding AI-specific bonuses tied to customer AI adoption rates and the business impact customers achieve.

The career path often leads to:

Senior Success Manager specializing in AI strategy
Director of Customer Success or AI Customer Success
Vice President of Customer Experience
Consulting or entrepreneurship leveraging B2SMB and AI expertise

Key Takeaway: The Customer Success Manager role is being transformed by AI from an operational, reactive function to a strategic, proactive role that requires technical knowledge, business acumen, and consulting skills.

What This Means for You:

If you’re currently in a CSM role or aspire to one:

Expand beyond basic customer success (starting now):

Volunteer to become your team’s “AI expert”
Learn about your company’s AI features more deeply than required
Start proactively recommending AI implementations to your customers
Track and document the business impact of AI adoption in your accounts

Develop strategic consulting skills (next 6 months):

Practice conducting business reviews that focus on outcomes, not features
Learn to create customer success plans that include AI adoption roadmaps
Develop proficiency in ROI analysis and value demonstration
Build templates and playbooks for AI implementation

Position yourself as an AI success leader (ongoing):

Share AI success stories in team meetings and with leadership
Create internal resources to help other CSMs support AI adoption
Propose pilot programs or initiatives to improve AI adoption across the customer base
Build relationships with product and engineering teams to provide AI feature feedback

C. The AI-Powered Product Marketer: Marketing Outcomes, Not Features

Product marketing in the B2SMB space is undergoing a fundamental shift. As AI capabilities become table stakes across most software categories, simply listing “AI-powered” features is no longer differentiating. The winning product marketers are those who can articulate the specific business outcomes AI enables and the services that ensure customers actually achieve those outcomes.

The New Product Marketing Paradigm:

From Feature Lists to Outcome Stories: Rather than marketing messages like “Our platform includes AI-powered analytics,” the AI-Powered Product Marketer crafts narratives like “Restaurant owners using our AI-powered analytics identify their most profitable menu items within the first week and increase margins by an average of 12%.”

From Software to Solutions: Marketing shifts from promoting software capabilities to promoting complete solutions that include implementation support, ongoing optimization, and outcome guarantees. The product is no longer just software; it’s software plus services that ensure success.

From Technical Specs to Human Impact: Instead of explaining how the AI works (“uses machine learning algorithms to analyze customer behavior”), the focus shifts to the human impact (“save 5 hours per week on customer communication while improving response quality”).

Core Responsibilities:

Outcome-Based Messaging: Developing marketing messages and positioning that emphasize measurable business results rather than technical capabilities. This requires deep research into customer success stories and the ability to quantify impact.

Service Productization: Working with product and customer success teams to package implementation and optimization services in ways that can be marketed effectively. This might include creating tiered service packages, certification programs, or “done-for-you” offerings.

Vertical Specialization: Creating marketing materials, case studies, and sales enablement content specific to different SMB verticals. AI implementation looks very different for a dental practice versus a construction company, and marketing needs to reflect this.

Education Content Strategy: Developing thought leadership content that educates SMBs about AI implementation best practices, building the company’s authority as an expert in helping small businesses succeed with AI.

Sales Enablement: Creating tools and resources that help sales teams position AI capabilities effectively, including ROI calculators, implementation timelines, and objection handling guides specific to AI-related concerns.

Competitive Differentiation: Identifying and articulating what makes the company’s approach to AI implementation superior to competitors, often focusing on service and support rather than just features.

Required Skills:

Strategic Marketing Skills:

Outcome-based positioning and messaging
Customer research and story development
Competitive analysis and differentiation strategy
Go-to-market strategy and launch planning
Content strategy and thought leadership

B2SMB Expertise:

Deep understanding of SMB buyer psychology
Knowledge of SMB economics and ROI requirements
Empathy for SMB operational challenges
Familiarity with vertical-specific needs and language

AI Knowledge:

Understanding of AI capabilities and limitations
Ability to explain AI in accessible, non-technical language
Awareness of AI trends and emerging capabilities
Knowledge of common AI implementation challenges

Content and Communication Skills:

Exceptional writing and storytelling ability
Video content creation and presentation skills
Ability to create complex concepts simply
Sales enablement and training capabilities

Career Path and Compensation:

Product Marketing roles in B2SMB companies specializing in AI typically pay $90,000-$130,000 for mid-level positions, with senior roles and leadership positions reaching $140,000-$200,000 plus equity in venture-backed companies.

Career progression often leads to:

Senior Product Marketing Manager
Director of Product Marketing
Vice President of Marketing
Chief Marketing Officer
Strategic consulting or advisory roles

Key Takeaway: The AI-Powered Product Marketer role requires combining traditional product marketing skills with deep AI knowledge and a services mindset. Success comes from marketing complete solutions, not just software features.

What This Means for You:

To transition into or excel in AI-focused product marketing:

Build a portfolio of outcome-based content (next 3 months):

Rewrite existing product marketing materials to emphasize outcomes
Create 2-3 case studies showing the business impact of AI implementation
Develop an ROI calculator or assessment tool for AI adoption
Write thought leadership content about AI implementation best practices

Develop service marketing expertise (next 6 months):

Study how services companies market their offerings
Learn about productizing services and creating tiered packages
Interview customer success teams to understand implementation challenges
Create mock service packages for AI implementation

Become an AI storyteller (ongoing):

Master the art of explaining AI in accessible terms
Collect and share customer stories about AI success
Speak at events or in communities about AI marketing
Build a personal brand around outcome-focused B2SMB marketing

III. Building Your Future as a B2SMB Leader

A. Becoming an AI Integration Expert: Your Development Roadmap

Positioning yourself as an AI Integration expert requires a deliberate, systematic approach to building skills, creating proof of expertise, and establishing your reputation. Here’s a practical 12-month roadmap.

Months 1-3: Foundation Building

Technical Skills Development:

Week 1-4: Complete foundational training

Zapier Academy’s full curriculum (free, self-paced)
“APIs for Non-Programmers” course on Udemy or Coursera
Platform-specific training for major AI tools (OpenAI, Anthropic, Google AI)

Week 5-8: Hands-on practice

Build 3-5 simple automations connecting AI tools to common SMB software
Create a personal AI prompt library for different business use cases
Set up test environments for popular SMB platforms (HubSpot free tier, QuickBooks trial, etc.)

Week 9-12: Apply to real scenarios

Offer to help 2-3 small businesses implement AI (friends, family, local businesses)
Document the process thoroughly
Gather testimonials and results data

Business Knowledge:

Choose 2 SMB verticals to specialize in
Interview 5-10 business owners in these verticals about their workflows and challenges
Join industry-specific associations or communities
Read trade publications and understand vertical-specific terminology

What to accomplish by Month 3:

Basic technical proficiency with AI tools and integration platforms
2-3 documented implementation projects
Deep understanding of challenges in 2 target verticals
Initial network in target industries

Months 4-6: Proof of Expertise

Portfolio Development:

Create a professional portfolio site including:

Detailed case studies of your implementation projects
Industry-specific AI implementation frameworks you’ve developed
Video walkthroughs of your methodology
Client testimonials and quantified results
Downloadable resources (prompt templates, checklists, guides)

Thought Leadership:

Write and publish 4-6 substantial articles on topics like:

“The 5 Biggest Mistakes [Vertical] Makes When Implementing AI”
“A Step-by-Step AI Implementation Framework for [Vertical]”
“How [Vertical] Can Use AI to [Solve Specific Problem]”
“Why Most AI Implementations Fail (And How to Succeed)”

Publish on LinkedIn, Medium, or industry-specific publications.

Community Presence:

Join 3-5 communities where your target SMB customers gather
Contribute valuable insights consistently (5-10 comments weekly)
Host a webinar or workshop on AI implementation
Engage with other AI implementation professionals

What to accomplish by Month 6:

Professional portfolio demonstrating expertise
Published thought leadership establishing authority
Growing network in target verticals and AI community
5-7 completed implementation projects with results

Months 7-9: Monetization and Scaling

Service Productization:

Develop clear service offerings:

AI Implementation Audit (2-week engagement, $3,000-$5,000)
Done-With-You Implementation Program (90 days, $8,000-$15,000)
Done-For-You Implementation Package (60 days, $12,000-$25,000)
Ongoing Optimization Retainer ($1,500-$3,000/month)

Create professional service packages with:

Clear scope of work
Timeline and deliverables
Pricing and payment terms
Testimonials and case studies

Marketing and Lead Generation:

If consulting independently:

Launch outreach campaign to target SMBs
Leverage your network for referrals
Partner with complementary service providers (agencies, consultants, accountants)
Run targeted LinkedIn ads to decision-makers in your verticals

If seeking employment:

Apply to 10-15 highly targeted roles at companies building AI implementation services
Leverage your portfolio in interviews
Propose AI implementation roles at companies that don’t have them yet
Network with hiring managers in the B2SMB space

What to accomplish by Month 9:

Clear, packaged service offerings (whether selling independently or to employers)
Active pipeline of opportunities
10-12 total implementation projects completed
Growing reputation as an AI implementation expert

Months 10-12: Refinement and Growth

Methodology Refinement:

Based on your experience:

Document your implementation methodology in detail
Create templates, checklists, and tools that make delivery more efficient
Identify what works and what doesn’t across different verticals
Develop specialization in highest-ROI implementation types

Team Building or Career Advancement:

If consulting:

Consider hiring contractors or partners to expand capacity
Develop training materials to bring on team members
Explore productized offerings (courses, templates, software tools)

If employed:

Position for promotion or expanded responsibilities
Propose building an AI implementation team
Develop training programs for other team members
Seek speaking opportunities to raise your profile

Long-Term Positioning:

Write comprehensive guides or e-books
Speak at industry conferences
Build relationships with AI tool vendors for partnership opportunities
Consider developing software tools to support implementation work

What to accomplish by Month 12:

Established reputation as an AI Integration expert
Sustainable business model (either as consultant or employee)
Refined methodology that delivers consistent results
Clear path for continued growth and scaling

Key Takeaway: Becoming an AI Integration expert is a deliberate process that requires technical skill building, hands-on experience, proof of expertise, and consistent marketing of your capabilities. The 12-month timeline is aggressive but achievable for motivated professionals.

What This Means for You:

Start this week by:

Assessing your current state: Where are you today versus the Month 3 goals?
Creating your personalized roadmap: Adapt the timeline based on your starting point and goals
Committing to specific weekly actions: Block time for learning, practice, and content creation
Finding an accountability partner: Someone also building AI expertise who can provide feedback and motivation
Tracking your progress: Use a simple spreadsheet or project management tool to monitor completion of milestones

B. The Entrepreneurial Path: Launching Your B2SMB AI Consulting Practice

For experienced professionals with entrepreneurial inclinations, launching an independent AI implementation consulting practice offers significant upside. The barrier to entry is relatively low, demand is high and growing, and you can often command premium rates while maintaining excellent work-life balance.

Is Independent Consulting Right for You?

Before diving in, honestly assess whether you have the characteristics that lead to consulting success:

Required Attributes:

Comfort with income variability and client acquisition responsibility
Strong self-discipline and time management
Confidence in your expertise and ability to deliver results
Willingness to handle business operations (contracts, billing, taxes, etc.)
Network or ability to build one in your target market
Financial runway to sustain 3-6 months with limited income

Advantages of the Consulting Path:

Higher earning potential (successful consultants often earn 2-3x employee salaries)
Complete control over client selection, workload, and schedule
Ability to specialize deeply in your areas of interest
Direct connection to the value you create
Flexibility to scale up or down based on lifestyle goals

Challenges:

Income inconsistency, especially in the beginning
Need to manage all aspects of the business yourself
Isolation without team collaboration
Constant need to market yourself and find new clients
Lack of benefits (health insurance, retirement, etc.)

Building Your Practice: A Launch Plan

Phase 1: Pre-Launch (2-3 months before going full-time)

Validation:

Secure 2-3 pilot clients while still employed (evenings/weekends)
Test your service delivery model and pricing
Gather testimonials and case studies
Validate that you can reliably deliver results

Business Foundation:

Form an LLC or appropriate business entity
Open business banking account
Set up basic accounting system (QuickBooks, FreshBooks, or Wave)
Purchase necessary insurance (general liability, professional liability)
Create contracts and standard operating procedures

Brand and Marketing:

Build professional website with portfolio
Establish LinkedIn presence optimized for target clients
Create service packages with clear pricing
Develop core marketing materials (one-pagers, case studies, proposals)

Financial Planning:

Calculate your baseline monthly expenses
Set target monthly revenue goals (typically 2-3x your employee salary to account for taxes, benefits, and business expenses)
Build 3-6 month financial runway
Research health insurance options

Phase 2: Launch (Months 1-3)

Client Acquisition Focus:

Leverage existing network for first clients
Dedicate 50% of time to marketing and sales initially
Set goal of 3-5 discovery calls per week
Target 2-3 active projects to start

Service Delivery:

Over-deliver for initial clients to generate referrals
Document everything you do for process refinement
Request testimonials and case studies proactively
Identify opportunities for productization

Business Operations:

Establish consistent schedule and work practices
Implement project management system
Create client communication rhythms
Track time and expenses meticulously

Phase 3: Stabilization (Months 4-9)

Revenue Stability:

Aim for 60-80% capacity utilization
Balance project work with marketing time
Develop retainer clients for predictable income
Increase rates as demand grows

Process Refinement:

Create templates and tools to increase efficiency
Document your methodology thoroughly
Identify which services have highest ROI and client satisfaction
Eliminate or adjust low-value offerings

Marketing Maturity:

Shift from outbound to inbound lead generation
Increase content marketing efforts
Build strategic partnerships
Develop referral systems

Phase 4: Growth (Months 10-18)

Scaling Decisions:

Evaluate whether to remain solo or build a team
Consider productized offerings (courses, templates, software)
Explore partnership opportunities with tool vendors
Possibly develop vertical specialization offerings

Business Development:

Implement formal sales process
Build pipeline of opportunities
Increase rates based on demand and expertise
Selective client acceptance

Pricing Strategy and Revenue Models

Initial Pricing Considerations:

Start conservatively, then increase:

Implementation Audits: $2,500-$5,000 (2-3 days of work)
90-Day Implementation Programs: $8,000-$15,000
Done-For-You Implementation: $10,000-$25,000
Monthly Retainers: $1,500-$5,000

As you gain experience and reputation, premium practitioners charge:

Strategic Audits: $7,500-$15,000
Comprehensive Programs: $20,000-$50,000
Enterprise SMB Implementations: $30,000-$100,000
Monthly Advisory Retainers: $5,000-$15,000

Value-Based Pricing:

As you mature, shift from time-based to value-based pricing. If you can implement AI that saves a business $50,000 annually, charging $15,000 for implementation is easily justified.

Hybrid Models:

Many successful consultants combine:

Project fees for implementation
Success fees tied to measurable outcomes
Ongoing optimization retainers
Training and workshop revenue
Affiliate income from recommending tools

Key Takeaway: Independent consulting offers significant upside for experienced B2SMB professionals willing to handle the business development and operations responsibilities. Success requires careful planning, financial preparation, and systematic approach to building the practice.

What This Means for You:

If considering the consulting path, take these steps over the next 60 days:

Validate demand: Have conversations with 10 potential clients to assess interest and willingness to pay
Pilot test services: Take on 1-2 small projects while employed to test your delivery model
Build financial runway: Reduce expenses and save aggressively to create 6-month cushion
Create basic infrastructure: Form business entity, set up banking and accounting, get insurance
Make the decision: Either commit to a launch date or decide to build your expertise within an organization first

There’s no universally right answer. Some professionals thrive as consultants, while others prefer the structure, stability, and team environment of employment. Be honest about what will make you happiest and most successful.

C. Leading the Change: Internal Innovation and Advocacy

Not everyone wants to leave their current organization or start a consulting practice. For many professionals, the most impactful path is leading the transformation within their current B2SMB company, positioning themselves as internal champions of AI implementation services.

The Intrapreneur Advantage

Leading change from within offers unique advantages:

Access to existing customers and resources
Ability to test and iterate without personal financial risk
Team collaboration and support
Established brand and credibility to leverage
Opportunity for significant career advancement

Building the Internal Business Case

To successfully advocate for AI implementation services within your organization, you need to present a compelling business case that addresses leadership’s key concerns.

The Financial Argument:

Develop a model showing:

Revenue Opportunity:

Potential service revenue from implementation packages
Premium pricing opportunity for service-augmented tiers
Expansion revenue from higher AI feature adoption

Example: “If we offer AI implementation services to 10% of our 5,000 customers at an average of $5,000 per implementation, that’s $2.5M in new revenue annually.”

Retention Impact:

Improved retention rates for customers who successfully implement AI
Reduced churn from customers frustrated with AI complexity
Increased lifetime value from deeper product adoption

Example: “Customers with high AI adoption have 30% better retention. If implementation services increase AI adoption by 50%, we could reduce churn by 15%, preserving $X million in ARR.”

Competitive Differentiation:

Market positioning advantage
Sales cycle reduction from clearer value proposition
Win rate improvement against competitors offering software-only

Example: “Competitors are still selling features. If we sell outcomes enabled by services, we differentiate and can justify premium pricing.”

The Strategic Argument:

Position AI implementation services as aligned with broader company strategy:

Market Evolution: The B2SMB market is shifting toward service-augmented models. Being early to this trend provides first-mover advantage.

Product Stickiness: Deep AI implementation creates switching costs. Customers who have invested in configured, integrated, optimized AI systems are far less likely to churn.

Customer Intelligence: Implementation services create deeper customer relationships and better feedback loops, informing product development priorities.

The Pilot Proposal:

Rather than asking for massive upfront investment, propose a pilot program:

Phase 1 (60 days): Design and test AI implementation service offering

Select 10-15 pilot customers
Develop implementation methodology
Deliver service and measure results
Gather customer feedback

Phase 2 (90 days): Refine and scale

Update methodology based on learnings
Train additional team members
Expand to 30-50 customers
Develop marketing materials and sales enablement

Phase 3 (120 days): Full launch

Integrate into standard go-to-market motion
Launch marketing campaign
Scale team as needed
Track business impact

Metrics to Track:

Measure success through:

AI feature adoption rates (pilot participants vs. control group)
Customer retention and expansion rates
Net Promoter Score changes
Customer-reported ROI and satisfaction
Service revenue generated
Sales win rate and cycle time impact

Overcoming Internal Resistance

You’ll likely encounter objections. Here’s how to address common ones:

Objection: “We’re a software company, not a services company” Response: “The best software companies recognize that outcomes matter more than features. Implementation services ensure our customers achieve outcomes, which drives retention and advocacy. We’re not becoming a services company, we’re becoming an outcomes company.”

Objection: “Services don’t scale like software” Response: “You’re right that pure services have different economics. That’s why we’re proposing productized services with repeatable methodologies, group delivery options, and self-service components. Think of it as ‘software-enabled services’ with unit economics that work at scale.”

Objection: “Customers should be able to figure this out themselves” Response: “In an ideal world, yes. In reality, our data shows only 15% successfully adopt AI features without help. We can accept low adoption and the churn that follows, or we can help customers succeed and reap the retention and expansion benefits.”

Objection: “This will be expensive to build” Response: “I’m proposing we start with a lean pilot using existing team members who want to learn these skills. We can prove the model works with minimal investment, then scale based on demonstrated ROI.”

Building Your Coalition

Internal change rarely happens alone. Build support across the organization:

Product Team: Share insights about implementation challenges that inform product improvements and new feature development.

Sales Team: Show how implementation services can be a differentiator in competitive deals and justify premium pricing.

Customer Success Team: Frame this as evolution of CS role toward more strategic, valuable work that’s more satisfying for team members.

Finance Team: Present the revenue and retention impact in language they understand, with clear ROI calculations.

Marketing Team: Demonstrate how implementation services can be a core part of differentiated positioning and content strategy.

Executive Leadership: Connect AI implementation services to strategic priorities like market leadership, customer retention, and sustainable growth.

Key Takeaway: Leading internal change requires business acumen, coalition building, and patience. The professionals who successfully advocate for AI implementation services position themselves as strategic leaders, often earning significant career advancement.

What This Means for You:

To lead AI implementation services within your organization:

This Month:

Document current AI adoption rates and challenges
Interview 10-15 customers about their AI implementation experiences
Create a one-page pilot proposal with clear objectives and metrics
Identify 2-3 internal allies who would support this initiative

Next 60 Days:

Refine business case based on feedback
Present to immediate manager or relevant stakeholder
Volunteer to lead pilot program if approved
Begin building implementation methodology even if formal approval pending

Next 90 Days:

Execute pilot if approved
Document results meticulously
Share progress updates across organization
Prepare full launch proposal based on pilot results

Even if your initial proposal isn’t approved, the process of developing it demonstrates strategic thinking, customer empathy, and leadership potential. These qualities will serve your career regardless of the immediate outcome.

Conclusion: Your Path to B2SMB Leadership in the AI Era

The transformation of B2SMB from a product-focused to a service-augmented, implementation-centric industry is not a distant future trend. It’s happening now, and the professionals who recognize and act on this shift will define the next generation of B2SMB leadership.

The Core Insights

The Implementation Gap is Real and Growing: Small businesses want AI capabilities but cannot implement them alone. This gap represents career opportunity for professionals who can bridge it.

New Roles are Emerging: AI Implementation Consultants, evolved Customer Success Managers, and outcome-focused Product Marketers are becoming core functions at forward-thinking B2SMB companies.

Multiple Paths to Success: Whether as an employee, independent consultant, or internal change leader, there are viable paths to building a career around AI implementation expertise.

Technical Skills are Necessary but Not Sufficient: Success requires combining technical capability with business strategy, customer empathy, and communication skills.

Now is the Time to Act: The market is still early enough that professionals who establish themselves as AI implementation experts over the next 12-24 months will have significant competitive advantage.

Your Decision Point

You’ve now read all three parts of this series. You understand the current B2SMB landscape, you know how to position yourself and conduct an effective job search, and you see the emerging opportunity in AI implementation.

The question is: what will you do with this information?

Three Paths Forward:

The Employee Path: Position yourself as an AI implementation specialist within a B2SMB organization, leading the development of services that help customers succeed with AI.

Best for professionals who:

Value stability and team collaboration
Want to leverage organizational resources
Prefer defined structure and support
See opportunity to lead transformation within existing company

The Consultant Path: Launch an independent AI implementation consulting practice serving SMBs directly or through partnerships.

Best for professionals who:

Have entrepreneurial drive and risk tolerance
Value autonomy and flexibility
Have network or ability to generate clients
Want direct connection to value created

The Hybrid Path: Build AI implementation expertise within current role while developing consulting capabilities for future independence.

Best for professionals who:

Want to test consulting without full commitment
Need time to build financial runway
Want to de-risk transition through gradual shift
See value in maintaining employment while building side practice

The 30-Day Action Plan

Regardless of which path you choose, take these steps in the next 30 days:

Week 1: Assessment and Decision

Honestly evaluate your current skills against requirements for AI implementation roles
Decide which path (employee, consultant, or hybrid) aligns with your goals and circumstances
Identify 2 SMB verticals to specialize in
Set specific 3-month, 6-month, and 12-month goals

Week 2: Foundation Building

Enroll in technical training courses (Zapier Academy, API fundamentals)
Join 3-5 relevant communities (LinkedIn groups, industry associations, B2SMB forums)
Begin building AI prompt libraries and integration examples
Reach out to 5 people in target roles for informational interviews

Week 3: Proof of Expertise

Offer to help 1-2 small businesses implement AI
Begin documenting your implementation methodology
Start outlining case studies of your work
Write first article or LinkedIn post about AI implementation challenges

Week 4: Momentum and Planning

Complete first implementation project
Create basic portfolio site or page
Refine your 12-month roadmap based on learnings
Take first concrete step toward your chosen path (job applications, business entity formation, or internal pilot proposal)

The Fundamental Truth

The B2SMB professionals who will thrive over the next decade are not those with the most technical AI expertise. They’re not the best prompt engineers or the deepest machine learning specialists. They’re the professionals who combine moderate technical capability with deep customer empathy, strategic thinking, and the ability to bridge the gap between what’s possible with AI and what small businesses can realistically implement.

If you’ve read this far, you clearly have the curiosity, commitment, and strategic mindset to succeed in this transformation. The only question is whether you’ll act on what you now know.

The Opportunity Window

Market opportunities don’t remain open indefinitely. Right now, in March of 2026, we’re at the early stages of the AI implementation wave in B2SMB. Companies are just beginning to recognize the gap between selling AI features and ensuring customer success with AI. Independent consultants are just starting to build AI implementation practices. The professional services ecosystem around AI for SMBs is nascent.

This creates an unusual window where motivated professionals can establish themselves as experts without decades of experience. The person who starts building AI implementation expertise today will have a head start – albeit a rapidly diminishing one – on the person who waits until 2027 when the market is more crowded.

Your Legacy in B2SMB

Consider the impact you could have over the next 5-10 years. If you successfully help just 50 small businesses implement AI effectively over that time, you’ll have:

Saved thousands of hours of business owner time
Generated millions in increased revenue or reduced costs for those businesses
Preserved jobs and enabled growth at companies serving their communities
Advanced your own career while creating genuine value for others

This is the opportunity before you. Not just a career pivot or a new role, but the chance to be part of the transformation that brings sophisticated AI capabilities to the small businesses that form the backbone of the economy.

The Choice is Yours

You can bookmark this series and return to it “someday when the timing is better.” You can acknowledge the opportunity intellectually while taking no action. You can wait for your current company to create these roles or for the market to mature further.

Or you can start today. Choose one small action from the 30-day plan above. Complete it this week. Then choose another. Build momentum through consistent, deliberate action.

The B2SMB AI implementation opportunity is real. The path to capturing it is clear. The only variable is your commitment to walking that path.

Welcome to the future of B2SMB. Let’s build it together.

About This Series

This concludes the three-part series on navigating the B2SMB career landscape in the age of AI and economic uncertainty. Part 1 covered the current market realities and immediate career enhancement strategies. Part 2 provided tactical job search guidance for B2SMB professionals. Part 3 explored the emerging opportunity in AI implementation and how to position yourself to capture it.

For more resources on building your B2SMB career, join the conversation in B2SMB professional communities, follow thought leaders discussing AI implementation for small businesses, and most importantly, start implementing. Your future self will thank you for the actions you take today.

Question 3

Between the Lines Newsletter

It’s Not a You Thing.

February 26, 2026

The Conundrum of Common Problems, Isolated Solutions

It’s a WE problem.

We wait twenty months to get our CAC dollar back.

We have lost half our marketing email deliverability.

We have lost a third of our organic search.

We bought AI to go faster. We are going slower.

We see our website traffic is down, our post responses are down.

We’re down.

You know what all of these problems have in common?

We.

WE share these problems.

But are WE sharing the solutions?

Rivers burning. Paybacks dropping. Wishful thinking.

Those aren’t just snappy headlines to grab your attention.

We are living the same challenges in the same market at the same moment.

But we seem to be… alone.

The Try Harder Trap

The effort is not in question.

If you are encountering these “challenges” your effort is not in question.

Nor is your intelligence.

Nor is your will or your focus or your skills.

Walk into any enterprise organization right now and you will find smart, seasoned professionals working hardon truly confounding problems.

They are gritting their teeth, driving themselves.

Do more. Test new go-to-market approaches.

Do it differently. Rebuild the channel mix.

Do it over.Recast the forecast.

Do the prompt one more time.

The urgency is not manufactured.

It is everywhere, and it is accelerating.

And that urgency is becoming more urgent.

Nearly half of 4,702 CEOs across 105 countries said they do NOT believe their business will be viable in a decade without significant reinvention.

The hard work gets harder.

We are all trying harder.

Everyone is working on this.

Everyone is working on this.

Separately.

Going it Alone

Between the lines of these common problems lie thousands and thousands of leaders going it alone.

Right now, across this market, at the moment you are reading this, hundreds of leadership executives are trying to solve the same exact problems.

The collapse of search is not a “you problem.”

The cratering of email effectiveness is not a “you problem.”

The explosion of AI is not a “you problem.”

Hundreds of marketing leaders are rebuilding their channel strategy from scratch without knowing that three peers at comparable companies have already tried what they’re about to try, and failed, and learned something critical from it.

Hundreds of senior leaders are wrestling with how to govern AI inside their organizations. Yet 53% of those same C-Suite execs won’t even admit to their teams that they, too, are struggling with their own use of AI. I feel them.

But the shadow cast from this “lonely shame” models the worst in Leadership, and it darkens the culture.

It’s a shadow that an Ernst & Young survey of 1,000 U.S. workers found: 59% spend more time wrestling with AI tools than if they’d done the work by hand. But they keep trying.

The message from the top? Figure it out.

Not, in all honesty, “Hey, I’m struggling with this, too.”

To my kindred Marketing Leaders: the most recent Gartner CMO Spend Survey said that the majority of you do NOT have sufficient budgets to execute your strategy. Across the conference room table, your CFO’s pressure has intensified year over year. 63% of marketing leaders report it.

Grow faster. Get leaner. Raise your game. With less.

And do it yourself.

Without talking to anyone who has solved this.

Under the false assumption that those people can’t be found.

How do you search for it on LinkedIn?

Oh, wait, there are literally thousands telling you they have it ALL figured out!

Based on their years and years of leading big businesses and big teams and big budgets!

Right.

It feels like the Genuine Leaders with Solutions That Work live on the moon.

Listen to Yourself

Over the last few months, In the 100+ direct conversations I’ve had with Senior Leaders across this $2.5 Trillion “niche” market of B2SMB, the same themes surface with a consistency that stopped surprising me a long time ago.

“We’ve been asked to spend half as much to get twice as much,” one CMO of a mid-tier payroll services provider told me. “It was not a gentle ask.”

Another VP Marketing, leader in tech hardware: “We can’t keep up with how fast our site traffic is dropping. We can’t get a click. We know what’s going on but that isn’t helping us solve it.”

Said a Fortune 500 CSO, a woman who has been selling successfully to SMBs for decades : “AI is our competitor. It’s the only salesperson our customers will listen to.”

A phone call with one of my favorite SaaS founders – a call that was a full-scale bitch on our collapsing KPIs – ended with him saying, “Nice drowning with you!”

To be clear: NO ONE is giving up.

These are passionate over-achievers, all of them. They are not wired to surrender to a trend. Or bad numbers. Or job insecurity.

But I’ve now started asking, “Who do you talk to about this?”

And I am met with a shake of the head. Chin down. Clicking on a keyboard.

Look! Over There! Another You!

The 2024 MGI Membership Marketing Benchmarking Report, which surveyed 700 professional associations, found that 67% of professionals cite peer networking as the #1 reason they join.

I can attest. I’ve witnessed it first hand.

My “associations” include: NRF, NTA, SMPTE, 4As, LMA, and the rest of my career’s worth of alphabet noodles.

And then of course B2SMBI for the last 8 years (!)

I am the first to say that my career was built on the shoulders of peers who were generous (and strong) enough to lift me.

So I’m not surprised that the demand for peer connection is rising.

Because peer wisdom works.

The dialogues – the genuine, smartly focused problem solving sessions with fellow practitioners – are not found within your own four walls. Or on LinkedIn. And never on Teams.

We don’t solve problems on earnings calls. Or in performance reviews. Or frankly around every Executive Committee table I have sat around (6 in all) and even led.

The solutions live inside not just a single peer, but in the brains of a few connections, or a dozen, or hundreds.

Or maybe at the end of a long call when someone drops their guard long enough to say what is actually true.

What is actually true: the B2SMB market that I love so dearly is one of the most fragmented professional communities in business.

Peers simply do not talk to peers.

Problems that are universal are being solved as if they are unique.

In a bizarre twist, we take the fragmentation of our 33 Million customers and apply it to our own behaviors.

Lessons already learned the hard way are being learned again, by someone else, at full cost.

Is Isolation a Strategy?

I have to wonder. Because isolation really looks like a strategy.

I suppose in this market, at “this level,” you are supposed to have the answers.

That is the job.

You are the senior person in the room. You are the one the organization looks to when the channels stop working and the numbers go sideways and the board starts asking harder questions.

Admitting you’re not sure what to do next feels like a confession of failure.

So you don’t admit it. You go back to your team and work harder and optimize the funnel one more time and tell yourself the answer is just around the corner.

Small wonder, then. Your behavior.

Research published in Frontiers in Psychology in 2024 found that psychological safety is a prerequisite for sharing behavior.

Without that safety, people hide what they don’t know. At this level, not knowing is the one thing you cannot admit. So the knowledge that could solve the problem stays locked in your office.

61% of Senior Leaders say that isolation is actively impairing their performance.

The U.S. Surgeon General’s 2023 advisory on loneliness and isolation put a clinical frame on it: professional isolation reduces task performance, limits creativity, and impairs reasoning and decision-making.

71% of small and mid-size business Leaders experience that isolation at least occasionally.

I don’t quote those stats to brainstorm a motivational poster with you.

This is not a YOU problem. This is not a ME problem.

I just want to point out another twist of irony: that we value peer wisdom, connections, our network, and yet we take on our job alone.

Sad that in our “industries”, we have few mechanisms for peer-to-peer problem solving at scale.

There are conferences where everyone show-ponies their highlights. There are LinkedIn post-players that are always performatively “right.” There are chats that feel more like video-game trash-talking than anything.

There are few places where real, unguarded collaborative problem solving happens.

So the problems WE are facing compound and remain YOUR problem.

The CAC crisis gets worse because everyone is independently testing the same failed channel strategies without knowing they are duplicating work that has already been done and already failed.

The channel collapse accelerates because no one is coordinating a response to a shared infrastructure problem – I’m looking at you, Google.

The AI confusion deepens because the executives who most need to govern these tools are the least likely to admit they haven’t figured them out yet.

Isolation doesn’t just slow the solutions.

It compounds the damage. Geometrically, down the chain.

Putting Our Heads Together

In 2024, researchers Terekhin and Trinh published a systematic review in the Journal of Organizational Behavior, synthesizing the full body of existing research on peer development groups. Their conclusion: structured peer groups are a legitimate, documented intervention that improves executive effectiveness.

That word – intervention!

Our shared problems – problems that are mounting every day, that are becoming radioactive – require an intervention.

An intervention conducted in a circle.

With people living the same business crises alone.

Here’s what such a gathering is NOT:

a vendor pitching a solution
a consultant diagraming one
a self-proclaimed SME power-pointing one
an influencer with an infographic
anyone who claims expertise based solely on number of followers

We need to re-discover our campfires.

Pull up some logs. Talk. Listen.

The ground rules are simple:

No bullshit.

No performative anything.

No shame.

Because no one in the circle believes you are doing anything wrong.

YOU ARE NOT DOING ANYTHING WRONG!

The math breaks.

The playbooks burn.

The tools fail.

The solutions escape us.

But I am willing to place any bet on the table.

WE will crack some codes.

WE will walk away more capable.

Won’t call it a comeback.

We’ve been here for years.

Our solutions will come.

As WE return.

Question 4

Between the Lines Newsletter

Part 1: Are Small Businesses Moving Faster Than Us?

January 6, 2026

Part 1: Are Small Businesses Moving Faster Than Us?

Dave Walker

Fortune 50 CMO | Founder, B2SMB Institute | Building the Operating System for Enterprise→SMB Growth | Publisher, Between the Lines

January 6, 2026

Series Introduction

Everyone read the same headlines in 2025.

SMB confidence soared and stayed soaring.

Business formations hit 535,000 in November alone, on track for our 3rd record-setting year in the last five.

SMBs adopted AI (in its purest use form) at rapidly increasing rates. Some say as high as 92%.

That dead-sexy product category – “embedded finance” – suddenly found itself the center of attention, with 90% of SMBs deeming it “essential.”

Meanwhile, 46% of SMBs got hit by cyber-attacks this year, while only 17% had cyber-insurance.

Like you, my head is spinning with digits.

These numbers spiced up McKinsey reports and SMB podcasts and Google pitch decks and our own conference panels.

But here’s what I think most of us missed: we kept track of what was “happening” but we spent far too little time dissecting what it meant, or more to the point, what the numbers are foretelling.

And more importantly, I haven’t seen much conversation yet about what’s carrying forward into 2026 with enough force to reshape the $2.5 trillion small business marketplace.

That’s what momentum is. Not what happened. What’s still happening.

The patterns with mass and velocity.

Over the next three days, I’d like to open the conversation up to “Max Flow.”

Let’s start our series with five stories that show how SMBs are evolving faster than the 100s of the familiar B2SMB names who serve them.

1. SMBs Integrated AI Into Operations – In Huge Numbers

We absolutely blew it here.

Back in August, we read it wrong: the drumbeat of negative AI anecdotes and analysis we heard over the first half of 2025 from our constituency of B2SMB executives.

We heard that AI adoption amongst SMBs – what we named “AI2SMB” – had slowed greatly, even dried up, across our B2SMB Enterprise Member-base.

Made sense, we thought, as we heard endlessly that SMBs were struggling greatly with AI implementation – a struggle they were not getting help addressing from their familiar B2SMB vendors.

We figured that the almost universal observation of “market softness” meant that SMBs were souring on AI.

On the contrary.

SMBs were simply (and very quietly) adopting AI for their own needs and in their own way, and in many cases, outside the channels of major B2SMB Enterprises.

According to the rapidly evolving metrics tracking total AI adoption, Small Businesses are creating their own revolution.

Amongst many reports over the last 6 months, the aggregate numbers are becoming much clearer.

Typical is Counterpart’s Small Business Insights Report, which found 92% of small businesses had integrated AI into their operations.

58% report AI saving them over 20 hours per week.
70% rely on AI for automation.
Over 50% leverage it for research and analysis.
53% percent use AI-powered chatbots for customer service.

Counterpart called it the “fastest technology adoption curve in small business history,” outpacing smartphones and the internet.

SMBs didn’t wait for enterprise-grade or enterprise-generated AI solutions.

They found accessible tools and implemented them faster than Fortune 500s finished their C-Suite alignment debates.

This happened because AI became cheap and simple, not because it became enterprise-ready. Twenty dollars a month. Intuitive interfaces. Immediate value. Fitted to need. And most importantly, usable.

A coffee shop owner can suddenly answer customer, inventory, pricing and other core business questions with the same depth as Starbucks with a billion-dollar data science budget.

The technology that we presumed to require expert implementation and premium pricing is being adopted pragmatically by people who just want to save 5, 10 or 20 hours a week.

They’re not buying AI strategy. They’re buying time back.

For large-scaled B2SMB sellers, the value of your AI is rooted in what problem your AI solves for your SMB customer.

Like so many things “engineered” for SMB purchase, AI has no value if it doesn’t begin and end with an immediate, close-in problem solved.

AI in its most direct form is exactly what SMBs say they need: a problem solver.

If your solution requires explaining why your AI matters, you’ve already lost to the tool they found on YouTube that just works for them.

Q: What are you building that actually saves someone 20 hours a week? And can they get value from it in an afternoon, or do they need your implementation team first?

2. New Business Starts in 2025 Hit Another Record

The US Census Bureau’s December 2025 Business Formation Statistics reported 535,041 business applications in November 2025, up 7.1% from October.

The year averaged 478,800 new business formations per month, representing a 435% increase since 2004 when the average was approximately 110,000 per month.

Umm… your total addressable market grew by 19 million customers since 2020.

This cohort was born digital. They’re fluent in subscription software, expect consumer-grade experiences in business tools, and have zero patience for friction.

They learned about SaaS from Netflix, not from enterprise software sales cycles. They expect to sign up in three clicks, get value immediately, and switch providers without penalty if something better comes along.

Traditional B2SMB sales approaches built around demos, proposals, and annual contracts don’t match how this generation buys. They’re comparison shopping on review sites, testing products through free trials, and making purchase decisions before ever talking to sales.

And their asking Chat GPT for recommendations.

So – incoming reality check here – imagine your SMB customer evaluating your offering with the collective intelligence of all history?

For B2SMB sellers, this TAM-boom creates opportunity and challenge simultaneously. The market is enormous and growing. But your buyer personas from 2020, even 2023, are obsolete.

Your go-to-market strategy, product design, and customer success approaches must evolve to serve entrepreneurs who expect Stripe-level onboarding, Claude-level depth and Amazon-speed everything.

Can someone sign up for your product right now, without talking to sales, and get value in under five minutes? If not, you’re invisible to millions of new entrepreneurs entering the market.

3. 96% of SMBs Plan Payment Technology Upgrades

Business Wire recently reported that 96% of US SMBs accepting in-person transactions plan to upgrade their payments technology in the next 12 months.

Why? Because their customers are demanding it now.

Payments have rapidly evolved from background utility into strategic competitive advantage into tactical, practical necessity.

SMBs view payment innovation as a key driver of customer success and growth, not just a way to collect money.

The commoditization of basic payment processing is complete. SMBs now expect advanced capabilities like instant settlements, integrated financing, fraud protection, and data analytics as standard features.

When 90% of SMBs say they will pay premium prices for better payment efficiency, that’s a market explicitly telling you that payment friction is costing them customers.

The rise of BNPL, digital wallets, and embedded payments created new expectations for flexibility and convenience. Small businesses that offer superior payment experiences gain competitive advantages in customer acquisition and retention. Those that lag behind lose sales to competitors with smoother checkout.

For B2SMB sellers, payment capabilities have become table stakes, especially in retail, hospitality, and service sectors. The willingness of SMBs to pay premium prices for payment efficiency creates opportunities for differentiation and revenue growth, but only for platforms that treat payments as strategic, not operational.

Do you offer instant settlements, BNPL options, digital wallet integration, and fraud protection? If your payment features lag behind consumer expectations, you’re creating friction in the customer experience. What would it take to make payments invisible in your platform?

4. 90% of SMBs Now Call “Embedded Finance” Essential to Everything

In September 2025, PYMNTS found that 90% of SMBs say embedded finance (“the integration of banking and other financial services into nonfinancial apps and services”) is now essential to their operations.

Financial services have stopped being a separate vendor relationship.

SMBs now expect their day-to-day software to provide lending, process payments, and manage cash flow without leaving the platform.

This is about removing friction. When your business software can see your invoices, your revenue, and your cash flow but can’t advance you capital based on that data, that’s not a missing feature.

That’s a broken customer experience.

Shopify didn’t disrupt banking with superior financial technology. They disrupted it by doing what banks should have done years ago: meet customers where they already work.

Shopify proved that software platforms are now financial operating systems, and traditional boundaries between SaaS and financial services have collapsed.

For B2SMB sellers, the strategic question is simple: can your customers access capital, make payments, and manage finances without leaving your platform? If not, you’re creating friction that embedded-finance competitors will exploit. Every SaaS company without a financial services strategy is now competing with one hand tied behind their back.

Are you building embedded finance capabilities, partnering for them, or watching customers consolidate to platforms that already have them?

5. Did You Miss It? The Tax Man Changed Your 2026 Game for the Good

A brief trip into the dense jungle of the US tax code…

The US Chamber of Commerce reported in August 2025 that the Section 179 deduction was doubled to $2.5 million as part of the ‘One Big Beautiful Bill’ provisions. Additional changes included bonus depreciation modifications, R&E deduction updates, and employer credit expansions, all creating significant incentives for SMB capital investment and equipment purchases.

This is the equivalent of a 21% to 37% discount on qualified purchases, depending on tax bracket.

Yet most B2SMB sales teams aren’t leading with this story.

Section 179 allows SMBs to immediately expense qualified purchases rather than depreciating them over years.

For a business in the 30% tax bracket buying $100,000 in equipment, that’s $30,000 in immediate tax savings.

That’s not a nice-to-have benefit. That’s the difference between ‘maybe next quarter’ and ‘send the contract today.’

Most B2SMB sellers mention tax benefits in footnote disclaimers instead of leading with them. This misses fundamental SMB buying psychology.

Small business owners don’t just – and never have – buy product features.

They buy outcomes. And reducing tax liability is a tangible, measurable outcome.

For B2SMB sellers of capital equipment, technology, or other qualifying assets, tax incentives create natural buying windows.

Quarterly-ends aren’t about budget flushes. It’s about tax strategy. Every year-end deal could close faster if you led with ‘this investment pays for itself in tax savings before we even calculate operational ROI.’

Does your sales team know how to calculate Section 179 benefits for your specific solution? Can they articulate it in one sentence? If not, you’re leaving deals on the table while tax-savvy competitors close business.

Tomorrow, part 2 in our 2026 Momentum Report, found right here.

Question 5

Between the Lines Newsletter

Partnership Theater vs. Business Reality

December 17, 2025

Dave Walker

Fortune 50 CMO | Founder, B2SMB Institute | Building the Operating System for Enterprise→SMB Growth | Publisher, Between the Lines

December 17, 2025

Partnership Theater vs. Strategic Reality

Three press releases landed in my inbox over the last few weeks, each one breathless about “strategic partnerships” that would “transform” markets.

Here’s what none of them said: which company was desperate, which one was playing defense, and which one just figured out how to finally make money off the mid-market.

After 40 years watching companies announce partnerships (and sometimes being the person generating those announcements), I can tell you this: the gap between the lines of what they say and what they mean is where the real story lives.

So let’s take a little look…

Salesforce + OpenAI: When Your Competitor Forces Your Hand

What they announced: Expanded partnership bringing OpenAI’s AI into Salesforce Einstein. Better forecasting, smarter automation, personalized everything.

What they didn’t say: “Microsoft is eating our lunch with Copilot, and if we don’t move fast, enterprise customers are going to start wondering why they’re paying us this much for a CRM that feels increasingly… 2019.”

I spent 30+ years in Fortune 50 executive suites. I know what “expanded partnership” means. It means the first partnership wasn’t deep enough, wasn’t fast enough, or wasn’t scaring competitors enough.

Here’s what’s happening.

Salesforce had Einstein GPT, powered by their 2023 OpenAI partnership. It was fine. Respectable.

But then Microsoft went all-in on OpenAI, wiring GPT-4 into everything. Dynamics 365, Office 365, the works. Suddenly they’re not just selling enterprise software; they’re selling the future. And they’re doing it to Salesforce’s customers.

And Salesforce’s AI integration looked tentative, not transformative – sooo 2023.

So Salesforce went back to OpenAI. Not to partner (they were already partners). To partner harder. Deeper integration. More access. Better branding rights. The October announcement was effectively: “We’re still relevant, we promise.”

Industry analysts called it “necessary.” That’s analyst-speak for “they had no choice.”

What This Means If You’re Selling to SMBs

Two things are happening here that matter more than the press release admits.

First, the platform wars just went AI-native. Every B2SMB vendor is going to announce their AI partnership in the next 18 months. Most of them will be theater (a chatbot here, a recommendation engine there). Some will actually rearchitect their platforms. The difference will determine who wins the next decade.

Second, your SMB customers are soon going to expect AI-powered automation everywhere. Not just in their CRM. In their payroll system. In their inventory management software. In their HR. The Salesforce announcement just raised the bar for everyone, including those selling B2SMB.

If you’re running a B2SMB company and you don’t have an AI strategy that goes deeper than “we’re exploring ChatGPT integration,” you just got lapped.

Square + Grubhub: Playing Catch-Up by Skipping the Build

What they announced: Grubhub’s delivery network integrated into Square’s POS. One platform, all your channels, seamless operations.

What they didn’t say: “Square is toast in the restaurant vertical, thanks to Toast. We can’t build delivery infrastructure ourselves, and if we don’t move now, every restaurant is going to pick Toast by default.”

This one’s easier to decode because the competitive pressure is so obvious.

Toast built an all-in-one platform: hardware, software, payments, and integrated delivery. They own the whole stack.

Square owned payments and POS. Good, but incomplete. And in the restaurant world, incomplete means “we’ll look at you after we look at Toast.”

Square had two choices:

Build their own delivery network (2-3 years, $$$hundreds-of-millions)
Partner with someone who already has one (6 months, revenue share agreement)

They picked option 2. Pretty smart – but somewhat obvious – move.

Only one downside – and I’ve lived this one large: when you partner instead of build, you’re sharing the economics forever. Toast keeps all the margin. Square is now splitting it with Grubhub.

That’s fine if it holds the ramparts another day. It’s not fine if it becomes your permanent competitive position.

My second look? It’s Grubhub that needs this more than Square.

DoorDash and Uber Eats dominate delivery. Grubhub’s third place and fading. They needed distribution (access to a huge merchant base that wasn’t already using their competitors). Square gave them that.

This is a defensive partnership for both companies. Square defending against Toast. Grubhub defending against irrelevance.

When two companies team up because they’re both losing to someone else, that’s not innovation. That’s survival.

Not that there is anything wrong with survival.

At Toys R Us we bought an under-capitalized Baby Superstore chain because we absolutely sucked at our first few Babies R Us. We took defensive and made it offense.

What This Means If You’re Selling to SMBs

In B2SMB – and this is a forever thing – vertical-specific beats horizontal general-purpose. Every. Single. Time.

Square is a payments company trying to be a restaurant company. Toast is a restaurant company that happens to handle payments. See the difference?

If you’re selling horizontal infrastructure (payments, CRM, accounting), you’re going to lose to someone who built for a specific vertical unless you can assemble all the pieces they need faster than they can.

Square + Grubhub is what that assembly looks like when you’re playing from behind.

QuickBooks + Aprio & Rehmann: Superman to the Rescue

What they announced: Strategic partnerships with top accounting firms to implement Intuit Enterprise Suite in the mid-market. Accountants become implementation partners, advisory partners, growth partners.

What they didn’t say: “Intuit’s been losing mid-market customers to NetSuite for years, so we finally built an ERP that doesn’t suck, and we just figured out how to sell it without hiring 500 enterprise sales reps.”

Of the three partnerships, this is the only one that’s genuinely strategic.

It’s no secret, sort of a truism: Small businesses start on QuickBooks. They grow. And grow. And eventually after growing into mid-size businesses, QuickBooks can’t handle the complexity. So they switch to NetSuite, Sage Intacct, or Microsoft Dynamics.

Intuit loses them. It’s been happening for 20+ years.

But hang on: Intuit finally built an ERP that can compete: Intuit Enterprise Suite. Only one problem: mid-market buyers don’t trust software-platform companies to implement complex financial systems. They trust their accountants.

So Intuit did something most software companies don’t think of: they made SMEs in implementation (in this case accounting firms) the sales channel and the delivery channel.

This actually works because Accounting firms have three GTM problems:

Compliance revenue is commoditizing (everyone’s going cloud, it’s getting cheaper).
They need higher-margin advisory work.
Their clients keep asking them what system to switch to when they outgrow QuickBooks.

Intuit just solved all three.

Now when a client outgrows QuickBooks, the accounting firm doesn’t send them to NetSuite. They say: “Let me show you the Intuit Enterprise Suite. And we’ll implement it. And we’ll train your team. And we’ll help you redesign your workflows. And we’ll charge you for all of that.”

Accounting firms get advisory revenue. Intuit keeps the customer. The customer gets a trusted partner guiding them through the transition.

That’s not partnership theater. That’s structural GTM change.

What This Means If You Sell to the “M” in “SMB”

Not to be insulting, but for almost every SaaS player I’ve known, the best sales channel isn’t created by your own sales team. It’s someone your customer already trusts.

Intuit didn’t hire enterprise AEs. They didn’t build an inside sales team. They didn’t buy Super Bowl ads. They partnered with the people who already sit in the CFO’s office once a week/month/quarter.

If you’re trying to break upwards to mid-market or enterprise, ask yourself: who does your buyer already trust? And how can you turn them into your channel?

This is the partnership model everyone else should be copying.

So What’s Happening Between the Lines Here?

Three partnerships. Three different strategic rationales:

Salesforce + OpenAI: Defensive move. Microsoft forced their hand. They had to match or lose.
Square + Grubhub: Catch-up play. Toast was winning. This closes the gap but doesn’t win the war.
QuickBooks + Accounting Firms: Offensive move. This creates a structural advantage that competitors will struggle to replicate.

Here’s the pattern I see in our little $2.5Tril slice of heaven called B2SMB: partnerships announced as “strategic” are usually one of three things:

Integration Theater – API connection dressed up as transformation
Tactical Defense – Plugging a hole so customers stop leaving
Channel Innovation – Actually rethinking how you go to market

Which one do you think matters long-term?

If you’re selling to or serving SMBs, here’s my point: don’t read these Partnership press releases as if they’re honest. They’re not lying, exactly. But they’re not telling you what’s really happening. The real question is always: did a competitor force this move?

Watch who’s partnering because they have to vs. who’s partnering because they saw something first. The first group is playing defense. The second group is playing offense. Bet on offense.

If you’re thinking about partnerships, ask the Intuit question: who does my customer already trust? That’s your channel.

And if you’re a services firm serving the B2SMB space (accounting, legal, payroll – whatever), pay attention to what Intuit just did. They turned their biggest churn problem into their biggest competitive advantage by integrating the trusted advisor into the sales channel.

That’s replicable. You should be thinking about how to replicate it.

What I’m Watching Next in Partnerships

Salesforce will need to announce something else in Q1. The OpenAI integration won’t be enough. They’re going to acquire or partner with someone in the vertical space (probably construction, healthcare, or professional services). They’ve learned from Toast that vertical focus wins.

Square will either announce another vertical partnership (I’m guessing contractors or professional services), or Block will spin Square out and let it actually become a restaurant company. They can’t keep playing horizontal against vertical players.

Intuit will sign 3-5 more large-network accounting firms by March. This model prints money once you prove it works. Every top-50 firm will want in.

You already know this: when one company figures out a better GTM model, everyone else copies it within 18 months.

So watch the Partnership announcements like you watch Knives Out. Read between the lines. Always something.

Next Between The Lines Newsletter Drop on 12/30: I’m tracking layoffs in B2SMB. Not the human story – which sucks – but the market signal story.

When three payroll companies cut headcount in the same quarter, they’re telling you something about where the SaaS payroll market is going. I’ll tell you what I’m seeing.

Meanwhile, what are you seeing between the lines? Where’s the competitive pressure forcing partnerships in your world?

I want to know, and the comments, like Kwik Stop, are always open.

PS – Watch for our Between the Lines “Year in Review” dropping January 7 in the big two-six.

Question 6

Between the Lines Newsletter

The 2026 B2SMB Career Guide – A Special 3-Part Between2Bs Series

November 11, 2025

The 2026 B2SMB Career Guide – A Special 3-Part Between2Bs Series

Dave Walker

Fortune 50 CMO | Founder, B2SMB Institute | Building the Operating System for Enterprise→SMB Growth | Publisher, Between the Lines

November 11, 2025

Part 1: Thriving in the Transformed B2SMB Market

If you work in the Business-to-Small-Business space, you’ve felt the ground shifting beneath your feet.

Tech layoffs.

AI disruption.

SMBs! Toughest sell on Planet Earth!

It’s a lot.

But here’s what I’ve learned after 14 years in this Business-to-Small-Business market: transformation always creates opportunity for those who know where to look.

Let me share what I believe is really happening in the “niche” of B2SMB right now and, more importantly, what you can do about it today to advance your highly-specialized career.

The Reality Check (And Why It’s Not All Bad News)

Yes, the tech layoffs hit hard. Countless B2SMB companies trimmed their teams. The ripple effects are real. Budget scrutiny has intensified, sales cycles have lengthened, and the job market is more competitive than it’s been in years.

But here’s the thing nobody’s talking about enough: this is also revealing who has sustainable business models. Companies that truly understand how to serve small businesses profitably are thriving. The ones that have just been riding the post-pandemic wave? Not so much.

More importantly, small businesses themselves are proving remarkably resilient. New business formation is still well above pre-pandemic levels. While enterprise clients cut budgets en masse, the SMB market is diversified across every industry imaginable, and spending more on technology and automation than ever.

$1.5 Trillion according to Gartner’s latest.

What this means for your B2SMB career: Stop chasing “stability” at big-name companies and start pursuing genuine B2SMB expertise. The professionals who deeply understand how to serve small businesses at scale will always be in demand, regardless of economic cycles.

The Solopreneur Revolution You Need to Understand

The fastest-growing segment in B2SMB isn’t traditional small businesses with employees. It’s solopreneurs and micro-businesses (1-5 people). Millions of people have launched independent ventures as freelance consultants, e-commerce operators, content creators, and specialized service providers.

These customers are technology-native, value-conscious, and community-oriented. They’ll DIY until complexity forces them to seek help. And here’s the key: they require completely different engagement strategies than traditional SMBs.

If marketing speaks to procurement teams instead of individual owners, if onboarding assumes someone has IT support, if pricing doesn’t acknowledge SMB budget reality, a massive opportunity is missed.

Action step: Choose 2-3 solopreneur-heavy verticals (think photographers, consultants, e-commerce sellers) and spend time in their communities this week. Reddit, Facebook groups, Discord servers. Listen to how they talk about their challenges. This is market research gold you can make your own.

AI Is Your Career Accelerant (If You Use It Right)

Let’s address the elephant in the room: AI and your job security.

The narrative around AI has been dominated by anxiety, but the reality for B2SMB professionals is far more nuanced. AI tools are augmenting our work, not replacing us. Professionals actively incorporating AI into their workflows are reporting 20-40% productivity gains.

Think about it: AI can handle prospect research, draft customer emails, analyze competitive positioning, generate content drafts, and synthesize customer feedback.

What it can’t do is build genuine relationships, exercise strategic judgment, or understand the emotional reality of a stressed small business owner making a buying decision.

The B2SMB professionals winning right now are treating AI like a co-pilot (not you, Microsoft.) They’re using it to eliminate the grunt work so they can focus on the high-value activities that actually require human EQ and empathy.

But here’s the uncomfortable truth: the job market is rapidly splitting into two groups.

Those who actively leverage AI and those who don’t. You need to be in the first group.

Must-have AI skills for your resume:

Prompt-engineering – or Promptsmanship – for business applications (not coding, just knowing how to get value from AI tools)
AI-augmented research and analysis
Workflow automation using platforms like Zapier with AI features
The ability to evaluate which AI tools actually help SMB customers
Expertise in AI-implementation and integration – not just systems but users/people
Understanding of AI ethics and data privacy

Start this week: Pick one AI tool relevant to your role. I have favorites and you will too. Test-drive ChatGPT for prospecting emails. Try Claude for research and analysis. Try Jasper for strategic insights. Use at least 3 daily for two weeks. Document your productivity gains. This becomes your interview story: “I increased my output by X% using AI for Y, which freed me to focus on Z.”

The Implementation Gap: Your Biggest Career Opportunity

No secret: I love me some AI.

I believe it as revolutionary for SMBs as the internet. As ubiquitous as electricity.

I have cheered as B2SMB companies race to add AI features to their products. Sales decks are full of “AI-powered” capabilities.

But 70% of SMB owners who purchase these tools can’t actually implement them successfully.

This gap between purchase and productive-use is massive.

And it represents the most significant career opportunity in B2SMB since – well – forever.

Small business owners don’t have time to configure AI tools, don’t have technical expertise to integrate systems, and don’t have organizational capacity to manage change.

They need help. Real, hands-on, “let me do this with you” help.

The next wave of successful B2SMB professionals won’t be those who build or sell AI features. It will be those who bridge the implementation gap. Who can conduct workflow audits, provide hands-on setup support, create industry-specific templates, and offer ongoing optimization.

Forward-thinking companies are already creating roles like “AI Implementation Specialist” and “AI Customer Success Manager.” Independent consultants are charging premium rates for implementation services. Agencies are adding “done-for-you” AI packages.

Position yourself now: Start thinking of yourself as an AI implementation specialist, not just a marketer/salesperson/product manager. Learn basic APIs and integration concepts. Study how agencies structure their engagements. Create repeatable frameworks for helping SMBs adopt AI tools. Document and publish. Share on social. Shout it from the rooftops.

Two Actions That I Believe Will Make You Indispensable – They Did for Me

1. Become an Intrapreneur

The most effective career strategy right now isn’t job hopping. It’s making yourself invaluable in your current role by solving meaningful problems without being asked.

Look for inefficiencies that directly impact SMB customer satisfaction or retention. Maybe your onboarding loses 40% of customers in the first month. Maybe your sales team spends 60% of their time on admin instead of selling. Pick one problem, propose a specific solution with clear ROI, run a small pilot, document results, and evangelize success.

Even if your proposal isn’t immediately approved, you’ve demonstrated strategic thinking and initiative. That’s powerful in any future interview.

2. Upskill Strategically

Not all professional development is created equal. Be strategic about which skills you develop.

For marketers: HubSpot certifications (free), Google Analytics 4, Meta Blueprint
For sales: Sandler or Challenger methodology, MEDDPICC, Sales Navigator certifications
For product: Product-Led Growth Micro-MBA, Pragmatic Institute, Jobs-to-be-Done
For everyone: Basic SQL for data analysis, APIs and integration fundamentals

But a bit of gentle advice: don’t just collect certificates.

Create portfolio pieces that demonstrate your new skills in action…

Mock projects showing how you’d implement AI for a specific SMB vertical…

Analyses of B2SMB companies’ strategies with your recommendations…

Sample playbooks for SMB customers in a specific industry.

Your 90-Day Action Plan

Month 1:

Complete one free certification relevant to your role
Start using AI tools daily and documenting productivity gains
Identify three pain points in how your company serves SMB customers

Month 2:

Begin a paid course that addresses your biggest skill gap
Propose a solution to one of those pain points you identified
Join 3-5 B2SMB communities and start engaging

Month 3:

Create a portfolio piece demonstrating your new skills
Run a pilot of your proposed solution (even informally)
Apply your AI skills to a real work challenge and track results

The Bottom Line

The B2SMB landscape has fundamentally changed, but change creates opportunity.

The professionals who will thrive are those who:

Embrace SMB resilience as a career foundation
Treat AI as a force multiplier, not a threat
Recognize the implementation gap as their next big opportunity
Take ownership of their development instead of waiting for permission

You don’t need to wait for market conditions to improve or for your company to provide direction. Start today. Pick one action from this article and do it this week.

The future of B2SMB belongs to professionals who combine deep customer empathy with AI literacy and implementation expertise.

That can be you.

What’s one action you’re committing to this week?

I’d love to hear in the comments.

This is Part 1 of a three-part series on navigating the B2SMB career landscape. Part 2 covers modern job search strategies (November 18 Newsletter Edition 25-46), and Part 3 explores the emerging AI implementation opportunity (November 25 Newsletter Edition 25-47.)

The expanded 82-page B2SMB Career Guide will be released in full on Wednesday, November 25.

Question 7

Partners Circle

BRIDGING INNOVATION WITH IMPACT

If You Serve SMBs at Scale
You Need Partners.

Join a dynamic community of Business Development Leaders
collaborating to create partnerships that align and accelerate real market growth.

・FIND・ LINK・ALIGN・SHARE・ALLY・ADVANCE・WIN・

The 2025 B2SMB Institute Leaders’ Forum

Kickstart Your
B2SMB Partnerships

Elevating B2SMBI’s founding principles of peer-to-peer networking, we offer an exclusive platform to work together with B2SMB peers .

・DISCOVER・BRIDGE・TEAM UP・COLLABORATE・SHARE・

PARTNERSHIP EVENTS

Live & virtual meet-ups that foster intros, inspire collaboration, and drive powerful alliances.

PARTNERSHIPS INTEL

Research, insights, and playbooks that focus on the “practice” of strategic B2SMB partnerships.

SHARED GROWTH

Moving AI2SMB from experimentation to scale via the collaborative effort of industry Leaders.

Join 100s of B2SMB Brands Now

Your Next Partner Is Inside Our B2SMB 300

THE B2SMB 300 IS YOUR PARTNERSHIP INTELLIGENCE HUB, POWERED BY AN AGENTIC FRONT-END TO FACILITATE USE AND VALUE.

Our exclusive “intelligent directory” of 300 B2SMB Enterprises spans Finance, Operations & Sales/Marketing offerings. Find pre-qualified partnership targets, market intel, and contact info, supported by a powerful Agentic interface. Access to Partners Circle Members only.

300 AI2SMB Sellers

30 1000+

LINKS

50+

PROMPT TEMPLATES

Partnership Resources on a Mission

Our mission is simple: to drive your Partnerships success in the $2.5 Trillion Small Business
marketplace. Tap into our online community, our tools, our library, and more.

Strategic Partnership Intelligence

WE KEEP YOU PARTNERSHIP-READY WITH MARKET INSIGHTS, COLLABORATION TRENDS, AND OPPORTUNITY MAPPING.

B2SMB Partnership Execs need data-driven insights to guide strategy, to identify ideal collaborators, and to structure successful agreements. We help anticipate common barriers, point out gaps, and offer case studies proven in our network. We deliver.

Partnership Development Guides

WE CROWD SOURCE - THEN LEVERAGE - WHAT OUR MEMBERS SAY WORKS, WHAT DOESN’T, AND WHAT'S POSSIBLE.

What’s the best way to develop best-in-class Partnership Guides? Partner with a best-in-class SME, like Bernhard Friedrichs of PartnerStandard. You need proven frameworks and methods to accelerate spark to fire, including playbooks on co-marketing, technology integration, and allied distribution. You’ll find them all here.

The First Network of B2SMB Brands

SINCE 2017, OUR B2SMB INSTITUTE NETWORK HAS BEEN PEER-POWERED. OUR PARTNERS CIRCLE IS MADE TO ELEVATE ALL.

We like being first: our Partners Circle is first in recognizing the power – and challenges – of B2SMB collaborations. Linking B2SMB Sellers, B2SMB technology platforms, and B2SMB service orgs, we “fill the briefcase” of your sales team. It’s time to get connected.

POWERFUL NETWORK OF STRATEGIC PARTNERS

LIKE OUR B2SMB INSTITUTE NETWORK, WE BELIEVE IN PEER-POWER. OUR PARTNERSHIP CIRCLE IS MADE TO ELEVATE ALL.

As a first-ever hub for B2SMB partnerships, we focus on how enterprises can collaborate with complementary B2SMB providers, technology platforms, and service organizations to accelerate capabilities for their SMB customers. Our connection point? A dedicated partnership matching platform and structured collaboration framework powered by PartnerStandard Council – where industry leaders define verified partnership standards and best practices.

CONNECT & COLLABORATE

Exclusive Partners Circle Events

OUR B2SMBI MEMBERS KNOW IT: LEADERS LEARN BEST FROM LEADERS - LIVE. JOIN YOUR PARTNERSHIPS PEERS FOR AN INSTANT UPGRADE.

Peer-to-peer, top-to-top, face-to-face. Our platforms for high-level networking, knowledge exchange, and direct engagement with B2SMB Leaders are must-make. Share challenges, solutions, best practices, resources and more with your Partnership counterparts.

Partners Circle Orientation

Virtual Partners
Circle Meet-ups

Small Group
Partner Workshops

Partner Ready?
Take Our Assessment

How ready are you for your next Partner, especially in the dynamic new AI2SMB
marketplace? Our 10-question diagnostic will help you assess.

Get in touch

Have more questions?

We love connecting with you and answering your questions about our events, our resources and our network. We’ll even chat you up on the Institute itself! If you don’t see your question in the FAQs, you can email us directly and we’ll return the favor within 24 business hours.

Question 8

AI2SMB

BRIDGING INNOVATION WITH IMPACT

It’s Time to Realize
AI’s Potential For Small Business.

Join a powerful new community of B2SMB professionals
collaborating to drive scaled AI2SMB adoption and success.

・Meet・Connect・Network・Learn ・Partner・Grow・

A FIRST OF ITS KIND HUB FOR AI SELLERS

If You Sell AI to SMBs You Need to Join Us.

Combining B2SMBI’s founding principles of peer-to-peer networking, shared learning and leadership growth, we turn our attention to AI2SMB. .

・SHARE・ SIMPLIFY・GUIDE・FOSTER・LINK・ACCELERATE ・

LIGHTHOUSE EVENTS

Live & virtual gatherings that foster AI2SMB understanding, best practices and collaboration.

THOUGHT LEADERSHIP

Research, insights, and playbooks that avoid hype and focus on the practical application of AI2SMB.

REAL MARKET GROWTH

Moving AI2SMB from experimentation to scale via the collaborative effort of industry Leaders.

Join 100s of B2SMB Brands Now

The hard numbers on AI2SMB adoption

OUR RECENT STATE OF AI2SMB REPORT OFFERS A PICTURE OF AI’S USE AMONGST SMBS. IT RAISES ALARMS FOR ALL.

Our purpose? To validate with hard numbers the current reality of AI adoption amongst SMBs. To identify the root causes and systemic barriers to AI use. And to offer B2SMB Enterprise Sellers recommendation on how to fully realize AI2SMB’s full potential.

92% SMBs

PLAN AI INVESTMENT

37% SMBs

PLAN TO USE AI IN 2025

70% SMBs

FEEL UNREADY FOR AI

49% Fewer

SMBs ADOPTING AI

A Growing Array of AI2SMB Resources

From live virtual meet-ups to our online community, from our newsletter and podcasts to our case study library, we’re a peer-driven hub for AI2SMB success – a bridge between Sellers and Buyers.

OUR VALUE

If You Are Selling AI to SMBs, You’ve Found a Trusted GTM Partner.

With a primary audience of senior-level Leaders at enterprises that sell at scale to SMBs, AI2SMB CoE helps:

Trusted Insights Into AI2SMB Trends

WE KEEP YOU AI2SMB FUTURE PROOF WITH ADOPTION TRENDS, USE CASES, PLAYBOOKS AND MORE.

AI2SMB Enterprise execs need data-driven insights to guide product development, messaging, and sales strategies, including insights into common barriers (cost, skills gap, uncertainty) and opportunities (productivity gains, marketing automation, etc.) We deliver.

Trusted Insights Into AI2SMB Trends

WE KEEP YOU AI2SMB FUTURE PROOF WITH ADOPTION TRENDS, USE CASES, PLAYBOOKS AND MORE.

AI2SMB Enterprise execs need data-driven insights to guide product development, messaging, and sales strategies, including insights into common barriers (cost, skills gap, uncertainty) and opportunities (productivity gains, marketing automation, etc.) We deliver.

Best-Practice Playbooks for Selling AI2SMB

WE SCOUR THE MARKET TO BRING YOU WHAT’S WORKING, WHAT’S NOT AND WHAT’S POSSIBLE TO WIN SMB AI BUYERS AT SCALE.

AI2SMB Enterprise execs need sales messaging frameworks and methods designed to help explain the value of AI for SMBs, and how their products embed AI in ways that actually matter. Bonus: we focus on ways to overcome both barriers and objections so prevalent in AI2SMB.

Best-Practice Playbooks for Selling AI2SMB

WE SCOUR THE MARKET TO BRING YOU WHAT’S WORKING, WHAT’S NOT AND WHAT’S POSSIBLE TO WIN SMB AI BUYERS AT SCALE.

AI2SMB Enterprise execs need sales messaging frameworks and methods designed to help explain the value of AI for SMBs, and how their products embed AI in ways that actually matter. Bonus: we focus on ways to overcome both barriers and objections so prevalent in AI2SMB.

A Powerful Network of AI2SMB Partners

LIKE OUR B2SMB INSTITUTE NETWORK, WE BELIEVE IN PEER-POWER. OUR TOP-TO-TOP COMMUNITY IS MADE TO ELEVATE ALL.

As a first-ever hub for AI2SMB, we focus on how enterprises can partner with AI startups, LLM platforms, and AI service providers to accelerate AI capabilities for their SMB customers. Our connection point? A dedicated networking platform powered by Key.ai.

Trusted Insights Into AI2SMB Trends

WE KEEP YOU AI2SMB FUTURE PROOF WITH ADOPTION TRENDS, USE CASES, PLAYBOOKS AND MORE.

AI2SMB Enterprise execs need data-driven insights to guide product development, messaging, and sales strategies, including insights into common barriers (cost, skills gap, uncertainty) and opportunities (productivity gains, marketing automation, etc.) We deliver.

Best-Practice Playbooks for Selling AI2SMB

WE SCOUR THE MARKET TO BRING YOU WHAT’S WORKING, WHAT’S NOT AND WHAT’S POSSIBLE TO WIN SMB AI BUYERS AT SCALE.

AI2SMB Enterprise execs need sales messaging frameworks and methods designed to help explain the value of AI for SMBs, and how their products embed AI in ways that actually matter. Bonus: we focus on ways to overcome both barriers and objections so prevalent in AI2SMB.

Best-Practice Playbooks for Selling AI2SMB

WE SCOUR THE MARKET TO BRING YOU WHAT’S WORKING, WHAT’S NOT AND WHAT’S POSSIBLE TO WIN SMB AI BUYERS AT SCALE.

AI2SMB Enterprise execs need sales messaging frameworks and methods designed to help explain the value of AI for SMBs, and how their products embed AI in ways that actually matter. Bonus: we focus on ways to overcome both barriers and objections so prevalent in AI2SMB.

A Powerful Network of AI2SMB Partners

LIKE OUR B2SMB INSTITUTE NETWORK, WE BELIEVE IN PEER-POWER. OUR TOP-TO-TOP COMMUNITY IS MADE TO ELEVATE ALL.

As a first-ever hub for AI2SMB, we focus on how enterprises can partner with AI startups, LLM platforms, and AI service providers to accelerate AI capabilities for their SMB customers. Our connection point? A dedicated networking platform powered by Key.ai.

CONNECT & COLLABORATE

Exclusive AI2SMB Events

OUR B2SMBI MEMBERS KNOW IT: LEADERS LEARN BEST FROM LEADERS - LIVE. JOIN YOUR PEERS TACKLING AI2SMB FOR AN INSTANT UPGRADE.

You are not alone! Our platforms for high-level networking, knowledge exchange, and direct engagement with the COE are must-make. Share challenges, solutions, opportunities, best practices, resources and more with your AI2SMB peers.

Top-to-Top Live Meetings

Virtual Meet-ups for Sellers

Small Group Roundtables

Healthy AI2SMB?
Take Our GTM Test Now!

The AI2SMB market will reach $48.5B by 2026, yet many Sellers are missing key GTM strategies and tactics to win their share. Take our simple 5-question diagnostic to identify strengths and gaps in your Playbook.

Get in touch

Have more questions?

We love connecting with you and answering your questions about our events, our resources and our network. We’ll even chat you up on the Institute itself! If you don’t see your question in the FAQs, you can email us directly and we’ll return the favor within 24 business hours.

Question 9

Leaders Forum 25 Agenda

THE NEW SELL OF
AI2SMB

THE B2SMBI 7th ANNUAL
LEADERS' FORUM DAY 1

If you sell AI-based products or services at scale to Small Business, this is your must-attend event.

The B2SMBI Leaders’ Forum brings together top executives from dozens of major brands to deliver actionable AI2SMB insights you can implement immediately.

Day 1 Delivers:
– Proven AI2SMB GTM Strategies — take home battle-tested approaches that have driven measurable AI2SMB acquisition and retention
– AI2SMB Implementation Roadmaps — receive practical blueprints for leveraging your AI offering to increase SMB acquisition and retention
– Complete Playbooks — leave with comprehensive frameworks you can deploy immediately
– Strategic Partnerships — connect with potential partners that force-multiply your GTM efforts

All while enjoying one-of-a-kind, fae-to-face networking in the beautiful Sonoma setting.

9:00AM-10:30AM

REGISTRATION

CHECK IN
You don’t need to present tickets – we got you! Pick up your badge, your swag, and your Speaker instructions (if you are indeed on stage.) If you haven’t already, please inform us of any dietary restrictions you might have.

9:00AM

SMART MUFFIN MEET-UP

PRE-EVENT WORKSHOP
We all have thoughts about AI’s impact, import and implication to SMBs, so let’s talk over coffee and “Smart Muffins” – see LI post for recipe! Join as you arrive, or arrive early – it’s a casual talk-around of what each of us is seeing, hearing and thinking about this revolution we’ve enjoined called AI2SMB. Bonus: a special surprise announcement.

Dave Walker

Co-Founder,

B2SMB Institute

10:30AM-10:45AM

"EVENT KICKOFF: WHAT TO EXPECT"

WELCOME
Nothing like that feeling of “lift-off” at one of our events! Dave Walker gives the 411 on our Leaders’ Forum 2-day agenda, on logistics of the venue, on our format and activities, on ground-rules for “no pressure” engagement, and on how to make the most out of your next 24 hours with your B2SMB Leadership peers. Let’s go!

Stefanie Lau

Community Director,

Key.ai

10:45AM-11:00AM

ONE BIG THING

MEET & GREET
As always, we start our event with an informal greeting on a mission – to work with a fellow-attendee to identify what’s the “one big thing” YOU want to take away from the Leaders’ Forum – with a little help from your friends!

Sangram Vajre

Co-Founder,

GTM Partners

11:00PM-11:25PM

WHEN HORSES GAVE WAY TO CARS:
A GTM FRAMEWORK

KEYNOTE
Over the course of two successful exits of more than $100Mil each, Sangram Vajre has been teaching the business of marketing with his signature frameworks. His best-seller, “Move” focuses on creating and executing effective go-to-market (GTM) strategies at any stage of a business’ lifecycle, a systematic approach to align and to grow effectively. He illustrates his concepts through real-world examples and practical guidance for implementation. As the B2SMB market continues to experience revolutionary change, GTM Playbooks have to change ahead of the waves impacting products, marketing, selling and delivery. Sangram’s framework is more than a guide, it helps you and your teams – well – MOVE!

Michel Rau

WW Director of Strategy,

Microsoft

Christopher Rubin

CCO,

BrandMultiplier.ai

Krishna Gandikota

Leader, Agentforce Customer Engineering - SMB,

Salesforce

11:25PM-11:50PM

GO-GO-GOING TO MARKET WITH AI

PANEL
Those three little letters – GTM – are most often followed by the word “plan.” But how do actually plan your GTM when your Market, and your product, and your customer are all undergoing daily change because of two little letters – AI? In the midst of what feels like a full-scale revolution brought about by “AI2SMB,” our panel will explore some ideas on how to frame GTM as a process, not a plan, and offer some specific ideas on taking your AI offering to market.

11:50PM-12:20PM

MOVE YOUR GTM

WORKSHOP
We’ll mix the bowl pretty good here in small groups of attending B2SMB Marketers, Developers and Sales Leads to apply the framework of Sangram Vajre’s “Move” to a hypothetical Seller of AI at scale to SMBs. We’ll step out of our own offerings to find means and methods of validating our GTM approach, and how to improve it.

12:20PM-12:50PM

FUEL FOR LEARNING

EARLY LUNCH
We won’t load you down with lots of carbs, but instead get your brains fueled for what promises to be a jammed Day 1. Grab a plate, enjoy the view, and start your engines!

Chris Shank

Vice President - Small Business Sales,

Verizon Business

Brian Bar

Founder/CEO,

Victory Lap

Rich DeGuzman

VP Sales

VensureHR

1:00PM-1:25PM

SALES LIGHTNING

PLAYBOOKS
Let’s talk Sales. And with so much Sales talent in our B2SMBI community, its an “embarrassment of riches” when selecting Leadership Execs to talk the front lines of winning SMB Business. We’ve tapped 4 of our best-and-brightest to “Inform – Instruct – Inspire” all of us from their highly successful Sales Leadership Playbooks. Buckle up!

Dave Raggio

VP,

Intuit SMB MediaLabs

Michael Marino

SVP - Commercial Sales,

Equifax

David McKie

VP BD/DataLicensing,

Yelp

Kelly Peters

VP Marketing,

Tomorrow.io

1:25PM-1:50PM

ON THE WINGS OF DATA

PANEL
Is your next AI2SMB opportunity hidden in plain sight? Our Panelists will share strategies for identifying overlooked data assets, overcoming implementation barriers, and measuring market impact—revealing that some of the most valuable data for innovation already exists within your organization.

Ivan Ostojic

Chief Business Officer,

InfoBip

1:50PM-2:15PM

THE SHAPE OF CX IN AN AI WORLD

KEYNOTE
In his recent column for the Forbes Business Council, InfoBip’s Chief Business Officer, Ivan Ostojic wrote: “The race to redefine customer experience (CX) is accelerating. As interactions between businesses, brands and their customers shift, I believe we will see significant developments across the critical layers of infrastructure, application and experience this year… From ever-evolving technology, business models, and delivery to hybrid AI deployment and scaling strategies, here are 10 predictions that I believe will shape CX in 2025.” Prepare for a provocative view ahead.

2:15PM-2:35PM

SMART COOKIES

BREAK

Venkat Krishnamurthy

Co-Founder/ President

Alignable

Carrissa Reiniger

Founder/CEO

Small Business Silver Lining

Amir Blich

CBDO

vcita.ai

2:35PM-3:00PM

A VIEW FROM THE TOP: 2025 EDITION

PANEL
By this point in our agenda, we’ll have digested a LOT. So now it’s time to get the perspective of the visionaries. We’ll talk the long view (well into next week!) of AI2SMB, managing the speed of change, picking winners, and negotiating all those curves!

Raj Mukherjee

Former Head of Product Development

GoDaddy & Indeed

3:00PM-3:15PM

THE AI2SMB IMPACT ZONES

Legendary Product Builder Raj Mukherjee (Indeed, GoDaddy) believes AI’s impact on SMBs hits 3 key areas: first, lowered barriers to customer acquisition. Second, lowered cost of operations. Then third? Greater opportunities for SMBs to radically re-imagine and transform their business. A tour of a visionary’s futures.

Take the Survey
Pre-Event!

3:15PM-3:40PM

ARE YOU AI2SMB READY?

WORKSHOP
We’ll once again break into small groups of attendees to answer our recent B2SMBI Survey, “Are You AI2SMB Ready?” Candid assessments are required! Let’s see how ready we think we are!

Kush Shrivastava

Founder/CEO,

Key.ai

Dave Walker

Co-Founder/CEO,

B2SMBI

3:40PM-4:05PM

HOW B2SMBI CAN DRIVE AI2SMB

DISCUSSION
If not us, who? As the global marketplace of Small Business continues to face rapid and radical change, The B2SMB Institute is keen to play a leadership role in what we’re calling “AI2SMB.” Dave Walker is joined by Kush Shrivastava to lead an all-hands discussion and feeback session on what our community needs to be successful in this enormous, volatile and challenging AI revolution.

Roland Ligtenberg

Co-Founder,

Housecall Pro

4:05PM-4:30PM

THE TRUST ACCELERATOR

Roland Ligtenberg, Housecall Pro Co-Founder, has built a community of 100K+ SMB customers by using “Community” as a “Trust Accelerator” to overcome skepticism toward tech sellers. From early Fuddruckers meet-ups with adopters to today, his community strategy has reduced sales friction, shortened cycles, and improved retention among solopreneurs. His playbook transforms tech introductions from pitches into dialogues, demonstrating why community-led growth is a foundational B2SMB strategy rather than just marketing jargon.

Dan Gliatta

Founder/Strategist

Cargo Agency

Cherie Edilson

Co-Founder/CEO

Member Marketplace

Patrick Foster

Co-Founder

Rada

Bryce Colburn

Moderator

Forbes

Ajay Moturi

Netflix ML Incubator

Nate Herkelman

Co-Founder

True Horizon AI

Joe Brown

Co-Founder/CEO

SMB.co

4:30PM-5:15PM

"INVALUABLE VERBATIMS" FROM NEW GEN/NOW GEN"

PANEL
A new twist to one of our event’s most popular segments. Dan Gliatta and Bryce Colburn moderate a group of 5 Small Businesses – who happen to be players in the B2SMB marketplace! All are young, hungry and facing the challenges of running an enterprise as both Operators and as Purveyors. We’ll talk about what they do to win SMB Business, AND what it takes to win their business. This highly interactive session allows all of us to hear from fresh voices: what moves an SMB to “Yes.”

5:15PM-6:30PM

"LET US ALWAYS BE FRIENDS..."

RECEPTION – WINE TASTING & CHARCUTERIE
“… or at least until this bottle ends!” It’s time to unwind as the Kunde Family Winery offers their very best to the weary attendees of the Leaders’ Forum. With long and beautiful views of the Sonoma Valley at sunset, we’ll share the day.

6:30PM

LEADERS' LEAGUE
EVENT DINNER
Sponsored by Verizon Business

We cordially invite ALL event attendees to join your peers for an extraordinary dinner in Kunde’s wine caves. We’ll be fed by Italian-trained culinary master, Chef Carlo Cavallo. After serving as Executive Chef for Giorgio Armani restaurants (earning “Best New Chef” from Los Angeles Magazine), Chef opened Meritage in Sonoma in 1999. The restaurant won “Best Seafood Restaurant” in Napa & Sonoma Counties for 14 consecutive years (2000-2014), alongside Thomas Keller’s Bouchon. Carlo won the “Best Beef in America Chefs Challenge” (2009) and three consecutive “Best Overall Martini” awards. In 2014, he launched Bistecca & Vino, an upscale Italian steakhouse. Selected for the prestigious Culinary Enrichment and Innovation Program (2018), he’s appeared on Food Network shows and has been featured in prominent publications like the New York Times and Wine Spectator. MANGIA!

THE NEW SELL OF
AI2SMB

THE B2SMBI 7th ANNUAL
LEADERS' FORUM DAY 2

Our agenda on Day 2 of the Leaders’ Forum dives deep into two key elements of “The New Sell”: Reach and Partnerships.

We’ll begin the day with with Intuit SMB Media Labs (sponsors of our Day 2 Brunch.) Our Speakers will talk optimizing an SMB-targeted Media Strategy and Plan.

We’ll also talk SMB Influencers – specifically turning them into some of your most efficient and effective lead sources.

Then we’ll convene our B2SMBI Partnerships Circle to talk collaboration within the explosive AI2SMB Marketplace. We’ll move beyond the theory of successful partnerships and get down into the nuts and bolts of finding, launching, managing and measuring cooperative marketing, selling, development and distribution.

We’ll start the day relatively early (been up late?) with a classic Sonoma brunch, wrapping our event up by noon.

8:30AM-9:25AM

BRUNCH

SPONSORED BY INTUIT SMALL BUSINESS MEDIALABS
A good evening demands a great brunch. Join us for a variety of fresh quiches, a local cheese + charcuterie board, fresh sliced fruits, yogurt / granola / blueberry parfaits and fresh baked croissants. Oh, and coffee. We’re going to need coffee.

Dave Walker

Co-Founder,

B2SMB Institute

9:25AM-9:30AM

INTRO TO DAY 2

INTRODUCTION
A key initiative for the Institute in the back-half of 2025: to help our Member organizations achieve breakthrough performance in reaching and engaging small business decision-makers through data-driven media strategies, innovative channel optimization, and deep audience understanding.

We’ll both present and seek feedback on the components of each “pillar of deliverables” from our nascent Media Resource Center:
– SMB Audience Intelligence
– Media Strategy Excellence
– Channel Innovation

Dave Raggio

Vice-President,

Intuit Small Business MediaLabs

9:30AM-9:55AM

A NEW KIND OF AUDIENCE SELECTION

KEYNOTE
Last year, Dave Raggio introduced Intuit’s Small Business MediaLabs, and we wondered why no one had really thought of the idea before: leverage your existing customer base like a media channel, rich with media strategic and tactical insights. Over the last 12 months, not only has the concept taken hold, it’s established a powerful and now proven way to grow your top of funnel.

Sagar Ganapaneni

Data Science & Analytics Leader,

Intuit Small Business MediaLabs

9:55AM-10:10AM

HOW SMBS ARE GOING TO MARKET

KEYNOTE
Small businesses in 2025 are treating advertising as a growth engine—driven by strategic intent, expanding budgets, and increasing confidence in their ability to reach the right audiences and measure real results. Across industries and firm sizes, SMBs are becoming more sophisticated advertisers, adopting advanced marketing technologies, diversifying their channel mix, and expecting ROI visibility as standard. In this session, we’ll explore the latest small business advertising trends shaping 2025—and what they mean for your strategy.

Melinda Emerson

President

SmallBizLady Enterprises

10:10AM-10:35AM

THE POWER OF INFLUENCE

PANEL
We’ve certainly heard that Partnerships can be “ships to nowhere.” Maybe that’s because we still struggle to understand the form, the function and the fundamentals of Partnership that really sail. We’ve assembled both SMEs and Partnership leads to unpack how to engineer collaboration for a complex B2SMB marketplace.

Rich Hargrave

Sr. Directory- Partnerships,

vcita

Alex Bellini

Founder/CEO,

Get Dandy

Sanjiv Parikh

VP of Client Growth,

Position2

Steve Strauss

Board Member,

SCORE

Suresh Madhuvarsu

Founder/CEO,

SalesTable

Jonathan Reisman

Founder,

Modwell

Juraj Pal

Head of Partnerships,

OpenPhone

Ben Pashman

Head of BD,

Creatify

10:35AM-10:55AM

PARTNER SHOWCASES

We’re dedicating time to hear from “Newbies” to B2SMBI alongside long-standing Members with “New News.” We’ve asked each of them to give a brief 5-minute-max pitch of their business, or update on their offerings, and most importantly what they both offer and need from our Partnerships Circle. Qs welcome!

10:55AM-11:30AM

PITCH FOR PARTNERS

Back by popular demand: we’ll invite attendees to stand and introduce their company, their partnership opportunities and what they’re looking for.
3-Minute time limit per Pitch!

11:30AM-11:45PM

RECAP OF PARTNERSHIPS CIRCLE MEET-UP

We’ll end Day 2 with summary take-aways and a commitment to meet within 14-days with prospective partners we’ve identified during the time together.

11:40AM-12:00PM

STEPS TOWARDS PARTNERSHIP

WALKABOUT
The Kunde Family Winery grounds afford us a number of paths to stroll – perfect places to casually engage in small group walkabouts. It’s an opportunity to meet and greet more of your Partnerships Circle attendees.

Question 10

Leaders’ Forum 25

The 2025 B2SMB Institute Leaders’ Forum

AI2SMB: The New Sell
To Small Business

If you sell AI-infused products at scale to Small Business, you need to be here. The B2SMBI Leaders’ Forum May 14th & 15th in Sonoma gathers Business-to-Small-Business peer-execs from dozens of brands to talk shop: the building, marketing, selling and future of AI2SMB.

・GROW BUSINESS・LEARN FROM PEERS ・ MAKE LIFE CONNECTIONS・

THE NEW SELL
How we grow at scale in a transformed SMB marketplace.

THE B2SMBI 7th ANNUAL
LEADERS' FORUM AGENDA

If you sell AI-based products or services at scale to Small Business, this is your must-attend event.

The B2SMBI Leaders’ Forum brings together top executives from dozens of major brands to deliver actionable AI2SMB insights you can implement immediately.

Day 1 Delivers:
– Proven AI2SMB GTM Strategies — take home battle-tested approaches that have driven measurable AI2SMB acquisition and retention
– AI2SMB Implementation Roadmaps — receive practical blueprints for leveraging your AI offering to increase SMB acquisition and retention
– Complete Playbooks — leave with comprehensive frameworks you can deploy immediately
– Strategic Partnerships — connect with potential partners that force-multiply your GTM efforts

All while enjoying one-of-a-kind, face-to-face networking in the beautiful Sonoma setting.

・DEVELOPMENT・MARKETING・SALES・DATA・SERVICE・INNOVATION・

Meet Your Peers

40+ Brands Attending LF25

We’ll continue to update our list of attending brands joining us in Sonoma.
And stay tuned for our Attendee List releasing the week of April 14!

YOU'VE FOUND YOUR PEEPS

SMBs Are the Toughest Sell on Planet Earth. We Got You.

Tough to reach, tough to engage and qualify, tough to close and keep – and 19 Million (!) new Entrepreneurs set up shop since 2020! No doubt B2SMB Pros like you are facing a challenging “New Sell.” We gather your Peers to learn from each other what’s working – and what’s not. Join us.

You’ve done a ton of work to understand your SMB customers and prospects, but they’re changing rapidly.

Since 2020, Small businesses have undergone a tsunami of change in the world around them, and like you, they’re trying to keep up with their customers. Think you’re alone? Think you’re the only one trying to get ahead? We got you.

You’re tired of learning EVERYTHING on your own time and dime. But who do you trust for expert advice?

Our own research suggests there are more than 150K pros like you whose job it is to win, keep and grow SMB customers at scale. And you thought you were alone! Our events introduce you to peers eager to share. We got you.

You’re gob-smacked every day by Small Business market complexity and fragmentation. You need responses that work.

Small businesses come in a vast variety of forms, sizes, and industries. You know snowflakes. Identifying the specific needs of these diverse customers can be complex and requires nuanced market research. We got you.

You’ve got competitors, sure - but some days you don’t know where the next big challenge is coming from - or how fast.

It’d sure be easier if everyone stayed in their lane, but new rivals are popping up all over, and often an SMB’s “share of wallet” is diverted into wholly new tech or solutions. So what is your competitive landscape? We got you.

Let’s Grow Us Some Leaders Like You.

Our events gather B2SMB peers to find and share success - winning Playbooks to take home, fresh ideas and perspectives, a shot in the arm and a partner on the journey.

・PART SUMMIT・PART MASTER CLASS ・PART FOOD FEST・ALL GOOD・

What Are We Talking About?

New Sell to SMBs

01. The Fluid State of AI2SMB

Revolutions move fast: how does AI impact what & how we sell to SMBs? Keynote SMEs, Practitioner Panels & Workshops.

02. A View from the AI2SMB Peers

Leaders want to hear from Leaders. As always, we bring you the most Senior-Execs, and time for Q&A/discussion.

03. Mastering Your AI2SMB GTM Plan

We’re in Go-to-market-choice overload, so we’re bringing in the Experts & Practitioners doing the work to sort it.

04. Defining Dev Excellence in AI2SMB

Builders will talk building AI2SMB products & services in all their forms – and how they plan to keep up the pace.

Featured AI2SMB Speakers:

Our roster of Sonoma Presenters are leading the AI2SMB revolution, providing essential insights into the products, services and Go-to-Market strategies and Playbooks that underlie a New Sell to SMBs.

KEYNOTE SPEAKER

WSJ Bestselling Author

Sangram Vajre - B2B GTM Guru

Named one of the Top 21 B2B Influencers in the world, with two $100Mil exits to his name, Sangram Vajre reveals the MOVE framework (Market, Operations, Velocity, Expansion) for transforming your GTM strategy at any stage of your business. He’ll teach us how to align our organizations and drive growth through practical examples that are pitch-perfect for our New Sell B2SMB Marketplace.

TRANSFORMING AI2SMB CX

Ivan Ostojic

CBO, InfoBip
Forbes Business Council

“The race to redefine customer experience is accelerating. We’re about to see significant developments across critical layers of infrastructure, application and experience.”

AN AGENT OF AGENTIC AI2SMB

Krishna Gandikota

Leader, Agentforce Engineering - SMB

“Our goal is to drive an Agent-first transformation of both Salesforce and of our many SMB customers across the globe, maximizing business value & digital transformation.”

A PLAYBOOK FOR AI2SMB GROWTH

Michel Rau

WW Director of Business Strategy, Microsoft

“The temptation to over-describe AI capabilities is counterproductive. I propose a consumer-centric approach, focusing on the benefits rather than technical details.”

Building to Billions

Roland Ligtenberg

Co-Founder/SVP Growth & Innovation, HouseCall Pro

“In under 6 years we’ve grown to 100,000+ home service professionals using our platform on average 7.25 hours a day – all through relentless zero-to-one execution.”

#1 SMB Influencer

Melinda Emerson

The Small Business Lady

“Your network equals your net worth. Develop deep, meaningful relationships with people who can help your business grow. And remember to look for ways to help them too.”

AI with Wisdom

Christopher Rubin

Chief Creative Officer, BrandMultiplier.AI

“When you marry the unparalleled efficiency of AI with real human insight you can elevate your brand with wisdom and warmth. Only true experience can offer both.”

Driving AI2SMB Scale

Michael Marino

SVP Commecial Sales- Emerging Markets, Equifax

“We have data assets for thinking more strategically about solving complex business challenges in the SMB Market, especially when it comes to Risk and Fraud prevention.”

In 76 Countries

Carissa Reiniger

Founder/CEO, Small Business Silver Lining

“We work relentlessly because when small businesses thrive their families are given opportunities, jobs are created, communities are invested in and the economy grows.”

TRUE EXPERIENCE

Chris Shank

Vice President, SMB Sales, Verizon Business

“When you marry the unparalleled efficiency of AI with real human insight you can elevate your brand with wisdom and warmth. Only true experience can offer both.”

Building from the Inside

Dave Raggio

Vice President, Intuit SMB Media Labs

“3 lessons as an Intrapreneur: socialize your idea early and often. Listen early and often. And don’t underestimate the consequences. Millions of SMBs are counting on us.”

Telling Stories of AI2SMB

Bryce Colburn

Managing Editor, SMB, Forbes Advisor

“The headlines are all about how AI is reshaping small businesses, helping them compete, innovate, and build stronger relationships. The story is just beginning.”

The Weather Channeler

Kelly Peters

VP Marketing, Tomorrow.io

“We want to help every business – large and small – manage their weather challenges and opportunities. We’re using AI to unlock one of the most dynamic data sets anywhere.”

Real Speed to Market

Amir Blich

Chief Business Development Officer, vcita

“One of the best life tips I picked up was given in a cult movie called Operation Grandma: You start the fastest you can and then slowly you pick up the pace.”

The Data Behind the Hub

David McKie

VP of BD & Data Licensing, Yelp

“Yelp was founded to bridge the gap between consumers looking for great local businesses and the entrepreneurs who run them. The data we’ve collected is powerful.”

Mining Connections

Raj Mukherjee

Former CPO, Indeed

“By analysing 100s-of- millions of qualifications and preferences from job seekers and employers, we make better connections. AI is a data-connection super-accelerant.”

27 Years of Selling
SMBs Fact-Based Choices

Erik Trusler

SVP, Sr. Marketing Officer & Business Development, Equifax

“Even from my days at YP, I learned every decision a Small Business makes counts. So we help them not just make decisions, but make informed, profitable, and secure choices.”

From Good to Great

Kush Shrivastava

Co-Founder/CEO, Key.ai

“The biggest difference I’ve observed between Good Product Managers and Great Product Managers is that the Great PMs understand and care for revenue equations.”

TRUE EXPERIENCE

Chris Shank

Vice President, SMB Sales, Verizon Business

“When you marry the unparalleled efficiency of AI with real human insight you can elevate your brand with wisdom and warmth. Only true experience can offer both.”

Featured AI2SMB Contributors:

Our Sonoma Attendees are leading AI2SMB in product development, marketing, sales and service. They’ll bring their experiences, their ambitions and their savvy to our time together. Find your next partner here!

Gavan Thorpe

CEO, Boostability

Michelle Winnett

Channel Partnerships, Square

Mark Kabana

Founder/CEO, Places Scout

Ashwin Ramesh

CEO, Synup

Elsa Chan

Head of Partnerships, Next Insurance

Vai Arunachalam

VP Product & Strategy, Turbify

Richard Lumsden

SVP, Soci

Robert Vogt

RVP - Strategic Partnerships, Yext

Giancarlo Gialle

VP Sales & Success, OpenPhone

Meg Beaudet

Head of Sales, Intuit SMB MediaLabs

Rich DeGuzman

VP Sales, VensureHR

Kimelyn Harris

Head of SMB Growth - Philanthropy, Wells Fargo

Sagar Ganapaneni

Data Science, Intuit SMB MediaLabs

Stefanie Lau

Community Director, Key AI

Ben Pashman

Head of Business Development, Creatify.ai

Sanjiv Parikh

VP of Client Growth, Position2

Steve Strauss

Board Member, SCORE

Ced Simpson

Founder, SMBConnect.co

Josh May

CEO/Founder, Powr.io

Everyone Leaves with One Big Thing - Plus...

We are very intentional at the Leaders’ Forum - we want our attendees to leave our events with the Big Things that make a mark, that make a breakthrough, that make a year.

Welcome to Kunde Family Winery, a successful small business since 1907.
What better spot to host our 7th annual Leader’s Forum!

LF25 HIGHLIGHT

“The Voice of
the Customer”
Live SMB Panel

We’ll reprise our most popular Leaders’ Forum segment of 2024 – our “Voice of the Customer” panel of local Small Businesses, in partnership with Alignable.

THIS LIVE DIALOGUE BETWEEN OUR AUDIENCE AND REAL SMBS PROVIDES INVALUABLE VERBATIMS.

7 Years of “The Favorite Event I Go To”

What if We Told You This Is NOT Your Typical B2B Event?

We’ve heard it so many times we’re truly humbled: the B2SMBI Leaders’ Forum is the year’s favorite event for many of our repeat-attendees.

Uniquely focused on B2SMB. Peer-SME Speakers. Future-forward content. Nice people. Casual. Fun. Your perfect fit.

Module 2

Your Module Headline Is Here

Cupcake ipsum dolor sit amet bear claw pie. Powder ice cream ice cream cake tart tart. Ice cream cupcake apple pie pastry shortbread sweet roll halvah caramels pudding.

Mention what your audiences will achieve after going through this module:

Module 3

Your Module Headline Is Here

Cupcake ipsum dolor sit amet bear claw pie. Powder ice cream ice cream cake tart tart. Ice cream cupcake apple pie pastry shortbread sweet roll halvah caramels pudding.

Mention what your audiences will achieve after going through this module:

Module 4

Your Module Headline Is Here

Cupcake ipsum dolor sit amet bear claw pie. Powder ice cream ice cream cake tart tart. Ice cream cupcake apple pie pastry shortbread sweet roll halvah caramels pudding.

Mention what your audiences will achieve after going through this module:

Hear from our students

"Highlight Testimonials from Your Amazing Students."

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Unlimited Access to the Tools Vault

Monthly Live Coaching Sessions

Accountability to Stay On Track

Study at the pace that works for you

Choose the payment options

Total Value of over $1,500

Best Value (Save $94)

One-time payment of

$647

The Online Course Name
Lifetime Access + Future Updates
BONUS: Tech Resource Library
BONUS: Done-for-you Swipe File
BONUS: Exclusive Access to Private Facebook Group for Students
BONUS: Weekly Live Q&A Call
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BONUS: Weekly Live Q&A Call
Payment plan does NOT include Pay In Full Bonuses

SINCE 2018, 1OOs OF EVENT-GOERS AGREE

The Voice of the Customer: Attendees Talk B2SMBI Events

“The keynotes, the panels, the breakouts and the 1:1 discussions at dinner all left us with wheels turning on how we can better help SMBs.”
– Kylie Raven, Google

“I am so incredibly impressed on who you’ve gathered together to talk about how we better support the SMB Community.”
– Eric Day, SVP/GM, DELL

“Everyone I speak with gives your events a “five star” rating – they really are very well done (and productive!)”
– Rich Hargrave,
Sr. Channel Sales Director,
vcita/inTandem

“It was a great event. The bar has been set even higher again.”
– Chris Shank, VP Sales, Verizon Business

“There was this great energy in the room and lots of good opportunities to network.”
– Kelly Thomas Nojaim, VP Partner Development, Microsoft

How it works

What Happens After You Purchase:

Step 1:

Enroll in the Course Now

Muffin wafer jujubes cake sweet roll apple pie donut sugar plum macaroon.

Step 2:

Check Your Email Inbox

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Step 3:

Get an Instant Access

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Join 100s of B2SMB Brands Now

LET’S TALK ABOUT FIT

Is the Leaders’ Forum for Me?

We like to think the B2SMB Institute is a hub for anyone who cares about Small Business – whether a large-scaled Seller, or a two-man Start-up, or an SMB Advocacy Org or policymaker, or an Influencer or a Media provider, or an Academic or student. If any of those remits describe you, we ARE you.

This Is RIGHT for You If:

You want to succeed at the job of winning, keeping and growing SMB customers at scale for a long, long time.
You alternately love and hate the challenge that is the Small Business. You are all-in to crack their code.
You feel a little lonely as a B2SMB pro. You’d like to meet some fellow travelers and share the journey.

This Is NOT for You If:

You Asked, We Answered

Frequently Asked Questions

We’ve been doing this for a spell, and we got some answers for the most FAQs lobbed our way.

What’s the dress code?

We like to call it Cali-Casual but you are as likely to see jackets and stylish outfits as you are polo shirts and sundresses. We do scissor gentlemen’s neck ties so you are forewarned! IT GETS COLD in the morning and at night, so dress in layers and for heaven’s sake bring a sweater/coat if you are naturally cold-blooded. Expect sunshine-soaked highs of 78-82 F and nights 50-55 F.

What’s expected of me?

Expected is such a strong word, but here’s our advice. You are experiencing that rare occasion as a professional when no one is evaluating your performance or clipping your wings for sport. It ain’t often you are amongst peers who genuinely want to give and get help. Bring your curiosity, your candor, your humor and your you.

Will I really meet people?

Let’s start at the fact that you will actually meet people – not just grab an obvious glance at their name-tag on the run. We intentionally keep the attendee list limited, so you can actually make genuine connections with everyone. You are amongst peers from a wide spectrum of brands (see 2024’s event page for clues.) We’re all naturally impressed with the fact that you love this B2SMB space as much as we do, and even more the SMBs that we serve. Lastly, many of our attendees have been here before – some for years – and they know how to welcome you. And if all else fails, submit to Dave’s “grab and deliver” with a “Hey, I gotta introduce you to ______.”

How do I meet Attendees ahead of time?

First, try our LinkedIn Company Page, follow and scan our growing community there. Beginning mid-April, we’ll launch registration for our “Meet Your Fellow Forum-Goers” program, where you can choose the attending Brands you’d like to connect with and we’ll make a warm intro via e-mail on your behalf. But like Match.com, this service is opt-in for both parties. As we think everyone would want it. As attendees commit we will update almost daily what new brands are joining us.

I’d like to set up some sales meetings at the event. Cool?

No. The Leaders’ Forum is a “sales pitch free” zone. We strongly discourage organizations and individuals whose sole reason for attending is to sell services to our Attendees. And we check all of our attendees ahead of time. While some may feel put off, we started the Institute as an antidote to a typical B2B event, where those being “sold” played duck-and-cover from the Sales folks. We don’t have Sponsors buy time on our stage to say/pitch whatever they want. That said, we do heartily encourage Partnership discoveries and dialogues, and we hope our attendees can and will draw the distinction and respect the no-pressure vibe we work so hard to create.

What events outside the main agenda are there?

First let’s talk about food. And wine. Those are events. We’ll be catering morning and noon and end-of-day (reception) on Day 1, morning and noon on Day 2. And karaoke or some such nonsense later on Night 1. Our Leaders’ League hosts an invite only Dinner on our first day as well (RSVPs are sent out about a week before the event.) We will try again to host a golf outing the afternoon of Day 2, so raise your hand if interested early please. Lastly, we purposely time the event for perhaps the most beautiful week in Wine Country. Arrive early, stay the weekend.

How do I best prepare for the logistics of the event?

You’ll see a list of hotels near the bottom of our event page. So there’s that. We’ll also send you an Attendee kit about 2 weeks before the event that features descriptions of our venue, maps of Sonoma and the wider Bay area, links to all our social platform and our in-event networking app. We have a great on-site and back-at-home team to help you get the most out of your Leaders’ Forum.

Will copies of presentations be provided?

Yes – our site will post the slideware presented within a week of the event. Our current plan is to video our keynotes and provide with their permission. If you are looking for a great handheld AI transcription tool, we really like Plaud.

Can you provide links to your social channels?

We thought you’d never ask. Find and connect to the Institute, Dave, Magic, et al. here here and here:

LINE UP FOR YOUR TICKET - NO CUTTING

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General Admission

NOW THRU 5/14

$1995

GENERAL ADMISSION $1995

Newbie Bird (Save 50%)

now thru 5/14

$997.50

If you've never been

By attending this event, you acknowledge and agree that the host organization, its partners, and affiliates may capture, record, and use photographs, video, or other visual or audio recordings of attendees, including your image, likeness, voice, and/or statements, for promotional, marketing, educational, and other purposes. These materials may be used in various media formats, including but not limited to social media, websites, brochures, advertisements, and other promotional or informational materials, without further notification, consent, or compensation to you. If you have concerns or wish to opt out, please notify the event organizers in advance or upon arrival.

LISTEN TO THE VOICE OF B2SMB

The Between2Bs Podcast

Join the growing audience of B2SMB Professionals listening every week to new episodes of Between2Bs. Added bonus? We release over a dozen new episodes around the Leaders’ Forum, featuring our event Speakers, Panelists and Special Guests, so stay tuned!

Sonoma -
The Chill One

After years in Napa, we came over the hill to the perfect vibe for our Leaders’ Forum. Sonoma is calm and cool, fresh and tasty, and so easy to love. Here just a few recommendations for your stay.

Host’s Pick 2025

Sonoma Valley Inn, Tapestry Collection By Hilton

550 2nd St W
Sonoma, CA 95476
(707)938-9200

4.5 star hotel

The Lodge at Sonoma Resort, Autograph Collection

1325 Broadway at Leveroni & Napa
Sonoma, CA 95476
(844)631-0595

4.5 Star hotel

The Inn at Sonoma, A Four Sisters Inn

630 Broadway
Sonoma, CA 95476
(888)568-9818

4 Star hotel

Fairmont Sonoma Mission Inn & Spa

100 Boyes Blvd
Sonoma, CA 95476
(888)905-8769

4 star hotel

The Meritage Resort And Spa

875 Bordeaux Way
Napa, CA 94558
(844) 521-8792

4.5 star hotel

The Knoll Hotel Napa Valley, Tapestry By Hilton

320 Soscol Ave
Napa, CA 94559
(877) 835-3680

Get in touch

Have more questions?

We love connecting with you and answering your questions about our events, our resources and our network. We’ll even chat you up on the Institute itself! If you don’t see your question in the FAQs, you can email us directly and we’ll return the favor within 24 business hours.

Searching for "playbooks"

You Made This.

From bitching to building, 8 years of B2SMBI

A Center of Gravity

October 3-4, 2017

The Covid Years

What Now Exists

I. State of the B2SMB Nation: Market Realities and Opportunities

A. The Economic Headwinds: Reading the Signal, Not Just the Noise

B. The SMB Resilience Factor: The Durability Advantage

C. The Rise of the “Indie” SMB: The Solopreneur Economy

II. The AI Revolution in B2SMB: Threat or Your Greatest Ally?

A. AI as a Job Enhancer, Not a Replacement

B. Must-Have AI Skills for Your Resume

C. The Emerging AI Service Gap: Beyond the Product

III. Actionable Steps for Immediate Career Enhancement

A. “Intrapreneurship”: Innovating from Within

B. Upskilling for the Future: Strategic Learning Investments

Conclusion: Positioning Yourself for the New B2SMB Reality

PART 2: The Modern B2SMB Job Search: Standing Out in a Crowded Field

I. Revamping Your Professional Brand for the B2SMB Niche

A. Beyond the Generic Resume: Becoming a B2SMB Specialist

B. Demonstrating Empathy for the SMB Owner

C. The Power of a Niche Portfolio

II. Networking in the New Era: Quality over Quantity

A. Identifying the “Right” Companies: Looking Beyond the Big Names

B. The Informational Interview is Not Dead: Strategic Relationship Building

C. Engaging in B2SMB Communities: Building Visibility and Authority

III. Nailing the B2SMB Interview

A. Answering the “Why B2SMB?” Question

B. The “Toughest Sell on Planet Earth”: Preparing for SMB Sales and Marketing Challenges

C. Asking the Right Questions: Evaluating Employer Commitment to SMB

Conclusion: Your Strategic Job Search Action Plan

Part 3: Future-Proofing Your B2SMB Career: The Rise of the AI Integrator

I. The New Value Proposition: From Vendor to Partner

A. The AI Implementation Chasm: Why SMBs Can’t Do This Alone

B. The “Done-For-You” and “Done-With-You” Models: New Service Paradigms

C. Case Study: The AI Implementation Specialist Role

II. Emerging Roles and Skill Sets for the AI-Centric B2SMB World

A. The AI Implementation Consultant: Strategic Workflow Design

B. The SMB Success Manager 2.0: Proactive AI Strategy and Optimization

C. The AI-Powered Product Marketer: Marketing Outcomes, Not Features

III. Building Your Future as a B2SMB Leader

A. Becoming an AI Integration Expert: Your Development Roadmap

B. The Entrepreneurial Path: Launching Your B2SMB AI Consulting Practice

C. Leading the Change: Internal Innovation and Advocacy

Conclusion: Your Path to B2SMB Leadership in the AI Era

The Conundrum of Common Problems, Isolated Solutions

The Try Harder Trap

Going it Alone

Listen to Yourself

Look! Over There! Another You!

Is Isolation a Strategy?

Putting Our Heads Together

Part 1: Are Small Businesses Moving Faster Than Us?

Series Introduction

1. SMBs Integrated AI Into Operations – In Huge Numbers

2. New Business Starts in 2025 Hit Another Record

3. 96% of SMBs Plan Payment Technology Upgrades

4. 90% of SMBs Now Call “Embedded Finance” Essential to Everything

5. Did You Miss It? The Tax Man Changed Your 2026 Game for the Good

Partnership Theater vs. Strategic Reality

Salesforce + OpenAI: When Your Competitor Forces Your Hand

What This Means If You’re Selling to SMBs

Square + Grubhub: Playing Catch-Up by Skipping the Build

What This Means If You’re Selling to SMBs

QuickBooks + Aprio & Rehmann: Superman to the Rescue

What This Means If You Sell to the “M” in “SMB”

So What’s Happening Between the Lines Here?

What I’m Watching Next in Partnerships

The 2026 B2SMB Career Guide – A Special 3-Part Between2Bs Series

Part 1: Thriving in the Transformed B2SMB Market

The Reality Check (And Why It’s Not All Bad News)

The Solopreneur Revolution You Need to Understand

AI Is Your Career Accelerant (If You Use It Right)

The Implementation Gap: Your Biggest Career Opportunity

Two Actions That I Believe Will Make You Indispensable – They Did for Me

Your 90-Day Action Plan

The Bottom Line

BRIDGING INNOVATION WITH IMPACT

If You Serve SMBs at Scale
You Need Partners.

Kickstart Your
B2SMB Partnerships

Virtual Partners
Circle Meet-ups

Small Group
Partner Workshops

Partner Ready?
Take Our Assessment

It’s Time to Realize
AI’s Potential For Small Business.