Recorded live at Trimble Insight 2025 in New Orleans, FreightWaves’ Thomas Wasson sits down with Jonah McIntire, Chief Platform Officer at Trimble Transportation, for a wide-ranging and refreshingly candid conversation about AI, software, and the future of logistics work. Jonah breaks down how Trimble operates at the “plumbing layer” of the supply chain, why tools like PC*MILER are still the industry’s ground truth, and why many past tech hype cycles—blockchain, visibility, buzzword AI—missed the mark. He doesn’t shy away from the hard truth: AI will eliminate back-office jobs, even as it radically increases productivity and reshapes how logistics companies scale. The conversation dives deep into AI-written code, self-connecting systems, rewriting legacy software in days instead of months, and why Trimble is betting on AI colleagues—not just AI features. From creative destruction to AI agents interviewing for dispatcher roles, this episode offers a rare, inside look at how one of the largest supply-chain software companies is rebuilding for the next decade. Follow the Loaded and Rolling Podcast Other FreightWaves Shows Learn more about your ad choices. Visit megaphone.fm/adchoices