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LEADERS FORUM 2026
NAPA, MAY 13-14

LEADERS' FORUM 25 GALLERY
JOIN LF 26 WAITING LIST

LEADERS FORUM 2026
NAPA, OCT 7-8

LEADERS' FORUM 25
JOIN LF 26 WAITING LIST
  • Between the Lines Newsletter

    Part 1: Are Small Businesses Moving Faster Than Us?

    • January 6, 2026

    In Are Small Businesses Moving Faster Than Us?, Dave Walker examines how SMBs outpaced B2SMB vendors in 2025, reshaping a $2.5 trillion market. Small businesses quietly adopted AI at unprecedented rates, optimized payments, and integrated embedded finance as essential operations tools. New business formations surged, creating a digitally fluent generation of buyers who expect frictionless onboarding and instant value. Meanwhile, tax incentives like Section 179 offer SMBs tangible financial outcomes that most vendors fail to leverage in their sales strategies. Walker warns B2SMB sellers: SMBs are moving faster than traditional playbooks anticipate, and success in 2026 will favor those who deliver solutions that save time, simplify operations, and reduce friction in immediate, measurable ways.

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  • Between the Lines Newsletter

    Partnership Theater vs. Business Reality

    • December 17, 2025

    In Are Small Businesses Moving Faster Than Us?, Dave Walker examines how SMBs outpaced B2SMB vendors in 2025, reshaping a $2.5 trillion market. Small businesses quietly adopted AI at unprecedented rates, optimized payments, and integrated embedded finance as essential operations tools. New business formations surged, creating a digitally fluent generation of buyers who expect frictionless onboarding and instant value. Meanwhile, tax incentives like Section 179 offer SMBs tangible financial outcomes that most vendors fail to leverage in their sales strategies. Walker warns B2SMB sellers: SMBs are moving faster than traditional playbooks anticipate, and success in 2026 will favor those who deliver solutions that save time, simplify operations, and reduce friction in immediate, measurable ways.

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  • Between the Lines Newsletter

    Part 3: Future-Proofing Your B2SMB Career

    • December 3, 2025

    In Future-Proofing Your B2SMB Career, Dave Walker outlines the massive opportunity arising from the AI implementation gap in small businesses. While most SMBs are eager to adopt AI, fewer than 20% use it effectively, creating demand for skilled professionals who can bridge the gap. Walker highlights three emerging roles—AI Implementation Consultant, SMB Success Manager 2.0, and AI-Powered Product Marketer—and provides a detailed 12-month roadmap to develop skills, build a portfolio, and scale impact. He also explores entrepreneurial and internal transformation paths, emphasizing service-augmented models, done-for-you and done-with-you approaches, and the value of outcome-driven implementation. The key takeaway: acting now to establish AI implementation expertise will create career leverage and long-term market advantage in the rapidly evolving B2SMB landscape.

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  • Between the Lines Newsletter

    The 2026 B2SMB Career Guide – A Special 3-Part Between2Bs Series

    • November 11, 2025

    In Thriving in the Transformed B2SMB Market, Dave Walker explores how the Business-to-Small-Business landscape is rapidly shifting due to AI, solopreneur growth, and economic disruption. He highlights the emerging career opportunities for B2SMB professionals who can bridge the AI implementation gap, providing hands-on guidance and strategic support to SMBs. Walker emphasizes the importance of treating AI as a productivity co-pilot, understanding solopreneur needs, and positioning oneself as an intrapreneur or implementation specialist. The article provides actionable 90-day steps—ranging from skill-building and certification to portfolio creation and pilot projects—helping professionals make themselves indispensable in the evolving market. The key message: B2SMB careers now reward empathy, technical literacy, and initiative.

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  • Between the Lines Newsletter

    Is AI Getting Impatient?

    • November 4, 2025

    In Is AI Getting Impatient?, Dave Walker explores the rapid evolution of AI-native companies in the B2SMB space, likening the surge to a Cambrian Explosion of business software. From autonomous financial systems like Digits to AI-powered sales reps like Artisan AI, Walker highlights how these emerging platforms are rewriting the rules for SMBs. The article emphasizes that traditional software “improvements” are no longer enough—success now demands building AI-first, unified, and industry-specific solutions. B2SMB leaders are challenged to shift from incremental upgrades to fundamentally new approaches, leveraging AI to automate, unify, and drive outcomes across finance, operations, and go-to-market. Walker’s key takeaway: AI isn’t waiting, and those who adapt first will define the next decade of B2SMB leadership.

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  • Between2Bs Podcast

    The AI2SMB Playbook You’ve Been

    • October 15, 2025

    Top SMB Tech Influencer John Lawson has thoughts on AI2SMB. From his early days showing how to tie bandanas on YouTube, to today’s bestseller, The Ultimate AI Marketing Manager, John’s surfed every major tech wave since 2000, and he’s talking why 77% of SMBs are still in their AI infancy.

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  • Between2Bs Podcast

    A Hard Conversation About AI2SMB

    • September 24, 2025

    Tech Pros from Vcita & AWeber reveal why 70% of small businesses feel “completely unprepared” for AI, but are they simply unprepared for the AI Big Enterprises are building for and selling to them? What if those same builders and sellers did the hard work for SMBs? Buckle up for the answers!

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  • Between2Bs Podcast

    Escaping Death Valley: Filling the Gap Between Marketing & Sales

    • September 17, 2025

    In this episode, Dave Walker speaks with Steve Prestidge from Centerfield about the evolving $2.5T B2SMB marketplace, the ever-growing challenge of winning, keeping and growing Small Business Customers at scale, and the ever-present “Death Valley” between enterprise marketing and sales. The conversation also touches on the importance of trust, the future of buying through comparison and deals, and how businesses can navigate the complexities of AI2SMB go-to-market.

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  • Between2Bs Podcast

    Erik Day, SVP of SMB, on How Dell is Solving AI Tech for Small Business

    • September 10, 2025

    90% of SMBs want AI, but only 15% implement it. Dell’s Erik Day reveals why most companies get AI go-to-market wrong and shares battle-tested strategies for moving prospects from experimentation to scale. Essential listening for tech sales pros.

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  • Between2Bs Podcast

    Verizon Business’ AI2SMB Product Team on Keeping It Simple

    • July 10, 2025

    On this week’s Between2Bs podcast, Randy Rector and Derek Peabody – Senior Directors of Product Development for Verizon Business – discuss their first AI offering for millions of Small Businesses: answering customer’s FAQs 24-7 via AI-enabled text. LISTEN NOW!

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