The Pragmatic Engineer

Hypergrowth startups: Uber and CloudKitchens with Charles-Axel Dein

24 Sep 2025

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Brought to You By:•⁠ Statsig ⁠ — ⁠ The unified platform for flags, analytics, experiments, and more. Statsig built a complete set of data tools that allow engineering teams to measure the impact of their work. This toolkit is SO valuable to so many teams, that OpenAI - who was a huge user of Statsig - decided to acquire the company, the news announced last week. Talk about validation! Check out Statsig.•⁠ Linear – The system for modern product development. Here’s an interesting story: OpenAI switched to Linear as a way to establish a shared vocabulary between teams. Every project now follows the same lifecycle, uses the same labels, and moves through the same states. Try Linear for yourself.—What does it take to do well at a hyper-growth company? In this episode of The Pragmatic Engineer, I sit down with Charles-Axel Dein, one of the first engineers at Uber, who later hired me there. Since then, he’s gone on to work at CloudKitchens. He’s also been maintaining the popular Professional programming reading list GitHub repo for 15 years, where he collects articles that made him a better programmer. In our conversation, we dig into what it’s really like to work inside companies that grow rapidly in scale and headcount. Charles shares what he’s learned about personal productivity, project management, incidents, interviewing, plus how to build flexible skills that hold up in fast-moving environments. Jump to interesting parts:• 10:41 – the reality of working inside a hyperscale company• 41:10 – the traits of high-performing engineers• 1:03:31 – Charles’ advice for getting hired in today’s job marketWe also discuss:• How to spot the signs of hypergrowth (and when it’s slowing down)• What sets high-performing engineers apart beyond shipping• Charles’s personal productivity tips, favorite reads, and how he uses reading to uplevel his skills• Strategic tips for building your resume and interviewing • How imposter syndrome is normal, and how leaning into it helps you grow• And much more!If you’re at a fast-growing company, considering joining one, or looking to land your next role, you won’t want to miss this practical advice on hiring, interviewing, productivity, leadership, and career growth.—Timestamps(00:00) Intro(04:04) Early days at Uber as engineer #20(08:12) CloudKitchens’ similarities with Uber(10:41) The reality of working at a hyperscale company(19:05) Tenancies and how Uber deployed new features(22:14) How CloudKitchens handles incidents(26:57) Hiring during fast-growth(34:09) Avoiding burnout(38:55) The popular Professional programming reading list repo(41:10) The traits of high-performing engineers (53:22) Project management tactics(1:03:31) How to get hired as a software engineer(1:12:26) How AI is changing hiring(1:19:26) Unexpected ways to thrive in fast-paced environments(1:20:45) Dealing with imposter syndrome (1:22:48) Book recommendations (1:27:26) The problem with survival bias (1:32:44) AI’s impact on software development (1:42:28) Rapid fire round—The Pragmatic Engineer deepdives relevant for this episode:•⁠ Software engineers leading projects•⁠ The Platform and Program split at Uber•⁠ Inside Uber’s move to the Cloud•⁠ How Uber built its observability platform•⁠ From Software Engineer to AI Engineer – with Janvi Kalra—Production and marketing by ⁠⁠⁠⁠⁠⁠⁠⁠https://penname.co/⁠⁠⁠⁠⁠⁠⁠⁠. For inquiries about sponsoring the podcast, email [email protected]. Get full access to The Pragmatic Engineer at newsletter.pragmaticengineer.com/subscribe

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The Pragmatic Engineer

Hypergrowth startups: Uber and CloudKitchens with Charles-Axel Dein

This episode hasn't been transcribed yet

Other episodes from The Pragmatic Engineer

Why Rust is different, with Alice Ryhl

TypeScript, C# and Turbo Pascal with Anders Hejlsberg

Designing Data-intensive Applications with Martin Kleppmann

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