Beyond The Prompt - How to use AI in your company

Rebuilding from Inside: How John Waldmann Led an AI Shift Without Breaking His Team


Listen Later

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 |
 

 

For more prompts, tips, and AI tools. Check out our website: https://www.beyondtheprompt.ai/ or follow Jeremy or Henrik on Linkedin:

Henrik: https://www.linkedin.com/in/werdelin
Jeremy: https://www.linkedin.com/in/jeremyutley

 

Show edited by Emma Cecilie Jensen. 

...more
View all episodesView all episodes
Download on the App Store

Beyond The Prompt - How to use AI in your companyBy Jeremy Utley & Henrik Werdelin

  • 4.8
  • 4.8
  • 4.8
  • 4.8
  • 4.8

4.8

48 ratings


More shows like Beyond The Prompt - How to use AI in your company

View all
NVIDIA AI Podcast by NVIDIA

NVIDIA AI Podcast

342 Listeners

Practical AI by Practical AI LLC

Practical AI

189 Listeners

Last Week in AI by Skynet Today

Last Week in AI

297 Listeners

Me, Myself, and AI by MIT Sloan Management Review

Me, Myself, and AI

107 Listeners

AI Chat: ChatGPT & AI News, Artificial Intelligence, OpenAI, Machine Learning by Jaeden Schafer

AI Chat: ChatGPT & AI News, Artificial Intelligence, OpenAI, Machine Learning

149 Listeners

AI Hustle: Make Money from AI and ChatGPT, Midjourney, NVIDIA, Anthropic, OpenAI by Jaeden Schafer and Jamie McCauley

AI Hustle: Make Money from AI and ChatGPT, Midjourney, NVIDIA, Anthropic, OpenAI

69 Listeners

This Day in AI Podcast by Michael Sharkey, Chris Sharkey

This Day in AI Podcast

201 Listeners

Leveraging AI by Isar Meitis

Leveraging AI

56 Listeners

The AI Daily Brief (Formerly The AI Breakdown): Artificial Intelligence News and Analysis by Nathaniel Whittemore

The AI Daily Brief (Formerly The AI Breakdown): Artificial Intelligence News and Analysis

509 Listeners

AI For Humans: Making Artificial Intelligence Fun & Practical by Kevin Pereira & Gavin Purcell

AI For Humans: Making Artificial Intelligence Fun & Practical

254 Listeners

Everyday AI Podcast – An AI and ChatGPT Podcast by Everyday AI

Everyday AI Podcast – An AI and ChatGPT Podcast

96 Listeners

A Beginner's Guide to AI by Dietmar Fischer

A Beginner's Guide to AI

44 Listeners

Using AI at Work: AI in the Workplace & Generative AI for Business Leaders by Chris Daigle

Using AI at Work: AI in the Workplace & Generative AI for Business Leaders

18 Listeners

The Next Wave - AI and The Future of Technology by Hubspot Media

The Next Wave - AI and The Future of Technology

61 Listeners

The TED AI Show by TED

The TED AI Show

45 Listeners