SMB career

Between the Lines Newsletter
Part 3: Future-Proofing Your B2SMB Career
- December 3, 2025
Part 3: Future-Proofing Your B2SMB Career

Dave Walker

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

December 3, 2025

We’re at an inflection point.

Over the past 18 months, virtually every B2SMB SaaS vendor has added “AI-powered” to their feature lists.

Sales teams tout machine learning capabilities.

Small business owners are being told AI will revolutionize their operations.

There’s just one massive problem: the vast majority of small businesses have no idea how to actually use these AI features effectively.

This gap, this chasm between what’s promised and what SMBs can realistically achieve, represents the most significant career opportunity in B2SMB since cloud computing.

Let’s show you exactly how to capture it.

The Implementation Gap Is Bigger Than Anyone Admits

The statistics should alarm every B2SMB company: while 70% of SMB owners express interest in AI tools, fewer than 20% have successfully implemented AI in any meaningful way. Among those who have adopted AI, most are using only a fraction of available capabilities.

Why is this happening? Three interconnected challenges:
- A Poverty in Time: Small business owners work 50-60 hours weekly handling multiple roles. The idea that they have time to watch tutorials, experiment with prompts, integrate systems, and optimize workflows is fantasy. A dental practice owner purchasing AI-powered patient communication needs to analyze workflows, configure the AI, integrate systems, train staff, and continuously optimize. Even if each task is “simple,” the cumulative time investment is prohibitive.
- A Technical Expertise Gap: AI tools require more sophistication than vendors acknowledge. Setting up automation workflows, connecting APIs, writing effective prompts, and troubleshooting integration issues require knowledge most SMB owners don’t possess. The “no-code” revolution made things easier, but “easier” isn’t the same as “easy.”
- A Strategy + Optimization Challenge: Effective AI implementation requires strategic thinking about workflows, priorities, and change management. An accounting firm might purchase AI document analysis software, but getting value requires rethinking their entire client onboarding process, deciding which documents to process automatically, training staff on reviewing outputs, and iterating based on accuracy.
These gaps create three distinct career opportunities for you:
1. As an employee of a B2SMB company creating implementation-focused roles
2. As an Independent Consultant helping SMBs implement AI
3. As an entrepreneur building “done-for-you” AI services
The professionals who establish themselves as AI implementation experts over the next 12-24 months will have extraordinary career leverage.

The Service Models That Are Winning

Forward-thinking B2SMB companies are shifting from product-centric to service-augmented models. Two approaches are emerging:
- The “Done-For-You” Model: The vendor or consultant takes full responsibility for implementing AI capabilities. A marketing agency might offer a “Done-For-You AI Content System” where they analyze the client’s brand voice, set up and configure AI tools, create custom prompts, establish quality control, train staff, and provide ongoing optimization. The client gets benefits without becoming an AI expert.
- Value proposition: SMBs will pay 2-5x premiums for done-for-you services because they eliminate risk, save enormous time, and deliver faster value. This also creates stickier relationships and additional revenue streams.
- The “Done-With-You” Model: The expert works collaboratively with the SMB, providing guidance while building the owner’s capability. A consultant might offer a 90-day program with bi-weekly implementation sessions, custom templates developed together, training on optimization, ongoing support, and a final session on independent maintenance.
- Value proposition: This balances expert guidance with knowledge transfer. Customers develop genuine competency rather than complete dependence, often resulting in better long-term adoption.
Many successful providers are merging these models and now offering tiered approaches:
- Basic (software only)
- Growth (software plus done-with-you support
- Premium (software plus done-for-you implementation).
This lets SMBs choose based on budget and capability while creating multiple revenue streams for the provider.

Three Emerging Roles You Should Really, Really Consider

1. AI Implementation Consultant: This role combines business strategy, technical capability, and customer success. Unlike traditional consultants who provide recommendations, implementation consultants get hands-on.
- Core responsibilities: workflow analysis, tool selection and configuration, integration architecture, prompt engineering and customization, training and knowledge transfer, ongoing optimization.
- Required skills: APIs and integration platforms, prompt engineering, data analysis, familiarity with SMB software ecosystems, process mapping, ROI analysis, change management, and exceptional ability to explain technical concepts plainly.
- Compensation: Employees earn $75,000-$150,000+ depending on level. Independent consultants charge $150-$300/hour or $5,000-$25,000 for fixed-price packages. The most successful specialize in specific verticals.
2. SMB Success Manager 2.0: the traditional Customer Success Manager role is evolving dramatically. Where CSMs previously focused on adoption and renewals reactively, the 2.0 role is proactive, strategic, and deeply focused on helping customers leverage AI for business outcomes.
- Required Skills: an evolution from reactive skills to proactive skills, from feature adoption to business outcomes, from generalist to AI strategist. These professionals proactively identify AI opportunities, focus on results rather than usage, and become trusted advisors guiding customers through the AI landscape.
- Compensation: $70,000-$160,000+ depending on level, often with bonuses tied to AI adoption rates and customer business impact.
3. AI-Powered Product Marketer: as AI capabilities become table stakes, simply listing features is no longer differentiating. Winning product marketers articulate specific business outcomes AI enables and the services ensuring customers achieve them.
- Required Skills: we are moving from product feature lists to business outcome stories, from software to complete solutions (software plus services), from technical specs to human impact. Instead of “AI-powered analytics,” it’s “Restaurant owners identify their most profitable menu items within the first week and increase margins by an average of 12%.” The skill sets that directly create outcomes will be critical, and highly valuable.
- Compensation: $90,000-$200,000+ depending on level and company stage.
Your 12-Month Development Roadmap

Months 1-3: Foundation Building

Build your technical/practical skills:
- Complete Zapier Academy, APIs for Non-Programmers course, platform-specific AI training
- Build 3-5 simple automations connecting AI to SMB software
- Create personal AI prompt library for business use cases
- Offer to help 2-3 small businesses implement AI (document thoroughly)
Deepen your Business knowledge:
- Choose 2 SMB verticals to specialize in
- Interview 5-10 business owners about workflows and challenges
- Join industry associations and communities
Months 4-6: Proof of Expertise

Develop your portfolio:
- Create professional portfolio site with detailed case studies
- Include industry-specific frameworks you’ve developed
- Add video walkthroughs of your methodology
- Gather client testimonials and quantified results
Stretch your Thought Leadership:
- Write and publish 4-6 substantial articles on topics like “The 5 Biggest Mistakes [Vertical] Makes Implementing AI”
- Join 3-5 communities and contribute consistently
- Host a webinar or workshop
Months 7-9: Scaling

Market what you’ve just built the last 6 months, and continue to build:
- If consulting: launch outreach, leverage network, partner with complementary providers
- If seeking employment: apply to targeted roles, leverage portfolio in interviews, propose new roles at companies
Months 10-12: Refinement and Growth

Practice ABR – “Always Be Refining”:
- Document your process in detail
- Create templates and tools for efficiency
- Develop specialization in highest-ROI implementations
Match the speed of AI growth:
- If consulting: consider hiring contractors, develop training materials, explore productized offerings
- If employed: position for promotion, propose building a team, develop training programs
The Entrepreneurial Path: Building Your Practice

For experienced professionals with entrepreneurial inclinations, independent consulting offers significant upside. Barrier to entry is low, demand is high, and you can command premium rates.

Is it right for you? You must have the following:
- comfort with income variability
- strong self-discipline
- confidence in expertise
- willingness to handle business operations
- a solid network or the ability to build one
- a financial runway of at least 3-6 months.
A sample Launch Plan:
- Pre-launch (2-3 months): Secure 2-3 pilot clients while employed, test delivery model, gather testimonials, form business entity, build website, develop contracts, create financial runway.
- Months 1-3: Focus on client acquisition (50% of time initially), over-deliver for initial clients, document everything, request testimonials proactively.
- Months 4-9: Aim for 60-80% capacity utilization, balance project work with marketing, develop retainer clients, refine processes, create templates.
- Months 10-18: Evaluate scaling decisions (solo vs. team), implement formal sales process, increase rates based on demand, become selective with clients.
Your pricing evolution:
- Start conservatively ($2,500-$15,000 for projects, $1,500-$5,000 monthly retainers), then increase as reputation grows.
- Premium practitioners charge $7,500-$100,000+ for comprehensive implementations and $5,000-$15,000 monthly retainers. Shift to value-based pricing over time.
Leading Change from Within

Not everyone wants to consult or change companies. Leading transformation within your current organization offers unique advantages: access to customers and resources, ability to test without personal financial risk, team collaboration, established brand credibility.

Building the internal business case:
- Financial argument: Show revenue opportunity from implementation services, retention impact from successful AI adoption, competitive differentiation enabling premium pricing.
- Strategic argument: Position as aligned with market evolution toward service-augmented models, product stickiness through deep implementation, customer intelligence informing product development.
- Pilot proposal: Don’t ask for massive investment. Propose 60-day pilot with 10-15 customers, 90-day refinement phase, then full launch. Track AI adoption rates, retention, NPS, service revenue, sales impact.
Overcoming objections:
- “We’re a software company” → “The best software companies recognize outcomes matter more than features”
- “Services don’t scale” → “We’re proposing productized services with repeatable methodologies and unit economics that work”
- “Customers should figure it out” → “Only 15% successfully adopt AI without help. We can accept low adoption and churn, or help customers succeed”
Build coalition across product, sales, CS, finance, marketing, and executive leadership.

The Bottom Line

The transformation of B2SMB from product-focused to implementation-centric is happening now. The professionals who recognize this and act will define the next generation of B2SMB leadership.

And in Conclusion…

Here’s what I hope you’ve learned: the AI implementation gap amongst SMBs is real and represents enormous career opportunity.
- New roles are emerging that combine technical capability with business strategy and customer empathy
- Multiple viable paths exist (employee, consultant, internal change leader)
- The market is early enough that professionals establishing expertise now will have significant advantage
Your next steps:
1. Assess your current skills against AI implementation requirements
2. Decide which path aligns with your goals (employee, consultant, hybrid)
3. Identify 2 SMB verticals to specialize in
4. Take one concrete action (enroll in training, offer to help a business, write your first article)
The opportunity window is open, but it won’t stay open forever.

The professionals who start building AI implementation expertise today will have a two-year head start on those who wait.

You have the roadmap. The question is whether you’ll walk the path.

What’s your first step going to be? I’m here to support you. Let’s do this!

This concludes the three-part series on navigating the B2SMB career landscape in the age of AI and economic uncertainty. Thank you for reading, and I wish you tremendous success in your B2SMB career journey.
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.