In this episode, John Waldmann, CEO of Homebase, shares how the 10-year-old SaaS company blew up its roadmap and rebuilt around AI—from culture to code. He walks us through the shift from 20-page PRDs to lightning-fast demos, reclaiming product leadership, and pushing teams into their “oh shit” moment with AI.

We explore the leadership reckoning, cultural resistance, and practical playbook behind the transformation—and what it means for the future of SaaS, small businesses, and human-centered AI. If you're leading (or bracing for) an AI shift, this one’s packed with hard-earned lessons and honest insight.

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 AI
00:31 Meet John Waldmann and the Story of Homebase
00:53 Reinventing Homebase as an AI-First Company
01:46 From PRDs to Prototypes: Building Faster, Learning Smarter
05:02 How AI Is Reshaping the Customer Experience
09:19 Culture Shock: Resistance, Skepticism, and AI Adoption
14:03 The End of SaaS as We Know It?
19:34 Leading Through Disruption: Ownership, Urgency, and Org Design
25:12 Forcing the Shift: Getting Teams to Embrace AI
27:50 Hiring the Unemployed—and Other Nontraditional Talent Bets
28:56 Curiosity > Credentials: What to Look for in AI-Ready Teams
31:57 New Expectations, OKRs, and Holding Teams Accountable
37:10 Serving Small Businesses Better with AI
44:52 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.

Season 5 | Episode 6 | Regional Teaching