GSBN’s Bertrand Chen sits down with Jonah McIntire, CTO and CPO of Trimble Transportation, for a masterclass on the future of LogTech, artificial intelligence, and the shifting economics of software.
Jonah shares his journey from working at LogTech startups to running a more than 1500 strong team of product managers and software engineers. In this episode, he pulls back the curtain on how a multi-billion dollar NASDAQ-listed company like Trimble is transitioning from the internet era to the AI Age on a dual tracks: the Tesla or Waymo way.
Jonah doesn’t mince his words: he explains why AI is a labor replacement tool, not just an “enabler,” and how Trimble is using “AI Colleagues” to automate everything from customer support to engineering. He also dives deep into AI safety, the “discretion problem” in social settings, and why the biggest bottleneck in 2026 isn’t technology—it’s human imagination.
For Jonah, given the Jagged Frontier of AI, the companies who understand what AIs are good and bad, will reap the benefits of deploying the technology for the right use cases first.
Key topics covered:
✅ AI Transformation Strategy – How to lead a large software organization through the “Jagged Frontier” of Generative AI.
✅ AI Safety & Ethics – The terrifying potential for “inhuman scale” sabotage and the challenge of teaching AI social discretion.
✅ Game Theory in Procurement – Why the settlement and negotiation space remains the most interesting “unsolved” problem in logistics.
🎧 A must-listen for product leaders, CTOs, supply chain professionals, and AI strategists looking to understand how the next decade of global trade will be built.
01:01 – Meet Jonah McIntire
02:55 – Path to CPO of Trimble Transportation?
06:02 – Trimble’s GPS humble beginnings
13:20 – AI is Labor Replacement.
14:50 – Trimble’s two AI Adoption Approach: Tesla vs Waymo
19:25 – Fully Automate Junior Devs
23:20 – Test-Driven Development with AI Envelope
33:00 – Expectations for Product Managers in this New AI World.
38:24 – Opportunities that come with AI Jaggedness
42:03 – Can AI Learn to “Lie”?
47:00 – AI Sabotage
50:30 – Is SaaS Cooked? Buy versus Build.
59:03 – The Only Remaining Business Moat
1:12:08 – Procurement Settlement: the Game Theory Frontier
Jonah shares his journey from working at LogTech startups to running a more than 1500 strong team of product managers and software engineers. In this episode, he pulls back the curtain on how a multi-billion dollar NASDAQ-listed company like Trimble is transitioning from the internet era to the AI Age on a dual tracks: the Tesla or Waymo way.