Brought to You By: • turbopuffer – a vector and full-text search engine built on object storage. It’s fast, cheap, and extremely scalable. • Entire – Git hosting, rebuilt for the agentic era. Every agent session, prompt and tool calls: stored in your repo. • Antithesis – verify your system’s correctness without human review or traditional integration tests – and avoid bugs or outages. — What’s changed in “the unwritten rules” of engineering management since the 2010s, what drove the shift to today, and what has it done to the engineer-to-CTO career path? Today’s guest is one of the best people I know who can tackle these questions. Will Larson is CTO of Imprint, was an engineering executive for 10+ years, and is the author of several popular books on engineering leadership, including ‘The Engineering Executive's Primer,’ ‘Staff Engineer, An Elegant Puzzle,’ and ‘Crafting Engineering Strategy.’ Previously, he was also CTO at Carta and Calm, and an engineering leader at Stripe and Uber. In this episode, we explore how engineering leadership has evolved from management practices shaped in the long post-financial-crisis ZIRP era to the altered expectations of engineers and managers today. Is middle management an increasingly precarious career path, and might managers need to reskill and return to hands-on technical work – or even consider retirement? Will makes the case, and we hear why the traditional path to engineering executive roles is changing, as well as why taking one step backward might sometimes be the best way forward. We discuss Will's early career, and get his first-hand account of Digg's disastrous relaunch, his own path to CTO, and he tells us why career ladders still matter. We also explore how AI is changing engineering roles and bringing technical decision-making back to leadership. Timestamps 00:00 Intro 08:20 Stories from Yahoo! 12:47 Digg’s v4 rewrite: the insider story 26:02 Will’s path to eng leadership 30:03 Uber, Stripe, Carta, and Calm 35:11 What does a CTO do? 38:09 Will’s role at Imprint 42:48 How engineering management has evolved 51:08 ZIRP’s impact on tech 57:21 Career ladders 1:01:03 Eng 1 vs Eng 2 1:06:58 How software engineering roles are changing 1:16:25 Revised rules of engineering leadership 1:21:57 The risks of becoming a bureaucrat as an EM 1:25:57 How to become a CTO? 1:31:33 Middle management vs. line management 1:41:36 Will’s writing 1:52:13 Book recommendations — The Pragmatic Engineer deepdives relevant for this episode: • The end of ZIRP and what it means for startups and the tech industry • Getting an Engineering Executive Job – an excerpt from Will’s book, The Engineering Executive's Primer • What is a Staff+ Engineer? • Inside Stripe’s engineering culture • Engineering career paths at Big Tech and startups • Staying technical as an engineering manager • Performance calibrations at tech companies • Scaling Uber with Thuan Pham (Uber’s first CTO) • Hypergrowth startups: Uber and CloudKitchens — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@pragmaticengineer.com. Get full access to The Pragmatic Engineer at newsletter.pragmaticengineer.com/subscribe
