Will Maier leads growth engineering at Stripe, where he's spent the last five years working across nearly every surface of the product. His background isn't CS — it's the history of science — and he's been through enough industry shifts (racking servers, the cloud transition, DevOps) to know when something really big is happening.
Find us now also on YouTube: @StaffEngPodcoast
In this season premiere of StaffEng, Will joins Alex and David to talk about what changed for him after November 2025, why he spent the holidays building a Lua distribution from his phone while doing laundry, and how he thinks about the organizational dynamics of AI adoption inside a large engineering org.
Topics covered:
- Why Will hasn't opened an IDE since November — and what replaced it
- The psychology of AI adoption: shame, hallucinated PRs, and "AI vegans"
- Skills as the new packages: how improvised markdown files are changing how teams share leverage
- Why measuring token usage (the wrong metric) surfaced the right insights
- The case for making the incident report critic, not the incident report writer
- What the cloud and DevOps transitions teach us about where AI is headed
