Rebuilding from Inside: How John Waldmann Led an AI Shift Without Breaking His Team
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What happens when a 10-year-old SaaS company blows up its roadmap and rebuilds itself around AI—from culture to code? In this episode, John Waldmann, Founder and CEO of Homebase, shares exactly how and why they did it. Homebase, a platform serving over 150,000 local businesses, has shifted from traditional development to a radically faster, prototype-driven approach powered by AI. But this isn’t just about new tools—it’s about reshaping the DNA of an entire organization. We explore how Homebase went from 20-page PRDs to live demos, why John had to reclaim product leadership to drive change, and what it means to push employees—gently or not—into their "oh shit" moment with AI. John opens up about the cultural friction, the leadership reckoning, and the tactical moves that made AI real across the company—from engineering to customer support. Plus, we zoom out: what does this transformation mean for small businesses, the future of SaaS, and how AI can actually bring teams closer to the humans they serve? Along the way, we dive into the tension between speed and craftsmanship, the underrated power of vertical software, and why inaction might be the most dangerous leadership choice of all. If you’re navigating an AI shift inside your company—or trying to figure out how to lead your team through one—this conversation is packed with battle-tested insight, hard-earned lessons, and a whole lot of real talk.**Key Takeaways: **

• **You Can’t Wait for Buy-In—Leadership Means Pushing the Shift **— John didn’t wait for excitement or alignment—he took back product leadership and forced the move toward AI. It wasn’t about consensus, it was about momentum. If you’re leading a team through this kind of shift, your job isn’t to ask for permission—it’s to create urgency before it's obvious.
• **Speed Over Specs — Prototypes Are the New Strategy **— Homebase moved from 20-page PRDs to live demos built in hours. That switch didn’t just make shipping faster—it changed the way teams learn, think, and listen to customers. The takeaway? Stop planning in the abstract. Ship something real, now.
• **Culture Is the Real AI Roadblock **— The hardest part of going AI-first isn’t tech—it’s trust, fear, and inertia. From engineers to support teams, John had to help people reach their “oh shit” moment with AI. That’s when change sticks. Until then, it’s just optional homework. Leaders need to make adoption inevitable.
• **AI Should Bring You Closer to Your Customers, Not Farther **— This episode isn’t about chasing shiny tools. It’s about using AI to reduce the noise—so your team can focus more on humans, not less. For John, pragmatic AI is about freeing up time, getting closer to customer problems, and making the org feel smaller, not colder.

LinkedIn: John Waldmann | LinkedIn)Homebase: All-in-one Employee Scheduling, Time Clocks, Payroll, & More | Homebase)

00:00 Introduction and Initial Reactions to AI00:31 Meet John Waldmann and the Story of Homebase00:53 Reinventing Homebase as an AI-First Company01:46 From PRDs to Prototypes: Building Faster, Learning Smarter05:02 How AI Is Reshaping the Customer Experience09:19 Culture Shock: Resistance, Skepticism, and AI Adoption14:03 The End of SaaS as We Know It?19:34 Leading Through Disruption: Ownership, Urgency, and Org Design25:12 Forcing the Shift: Getting Teams to Embrace AI27:50 Hiring the Unemployed—and Other Nontraditional Talent Bets28:56 Curiosity > Credentials: What to Look for in AI-Ready Teams31:57 New Expectations, OKRs, and Holding Teams Accountable37:10 Serving Small Businesses Better with AI44:52 Final Thoughts: Team Dynamics, Founder Risk, and What’s Next

📜 Read the transcript for this episode: Transcript of Rebuilding from Inside: How John Waldmann Led an AI Shift Without Breaking His Team |) 

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Show edited by Emma Cecilie Jensen.