Beyond the Prompt dives deep into the world of AI and its expanding impact on business and daily work. Hosted by Jeremy Utley of Stanford's d.school, alongside Henrik Werdelin, an entrepreneur known for starting BarkBox, prehype and other startups, each episode features conversations with innovators and leaders to uncover pragmatic stories of how organizations leverage AI to accelerate success. Learn creative strategies and actionable tactics you can apply right away as AI capabilities advance exponentially.
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Beyond the Prompt dives deep into the world of AI and its expanding impact on business and daily work. Hosted by Jeremy Utley of Stanford's d.school, alongside Henrik Werdelin, an entrepreneur known for starting BarkBox, prehype and other startups, each episode features conversations with innovators and leaders to uncover pragmatic stories of how organizations leverage AI to accelerate success. Learn creative strategies and actionable tactics you can apply right away as AI capabilities advance exponentially.
Rebuilding from Inside: How John Waldmann Led an AI Shift Without Breaking His Team
Beyond The Prompt - How to use AI in your company
52 minutes 29 seconds
4 months ago
Rebuilding from Inside: How John Waldmann Led an AI Shift Without Breaking His Team
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.
Beyond The Prompt - How to use AI in your company
Beyond the Prompt dives deep into the world of AI and its expanding impact on business and daily work. Hosted by Jeremy Utley of Stanford's d.school, alongside Henrik Werdelin, an entrepreneur known for starting BarkBox, prehype and other startups, each episode features conversations with innovators and leaders to uncover pragmatic stories of how organizations leverage AI to accelerate success. Learn creative strategies and actionable tactics you can apply right away as AI capabilities advance exponentially.
