StaffEng

I Haven't Opened an IDE Since November — Will Maier

David Noël-Romas (@davidnoelromas) and Alex Kessinger (@voidfiles) Season 2 Episode 1

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0:00 | 47:03

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.

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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