The Pragmatic Engineer

Hypergrowth startups: Uber and CloudKitchens with Charles-Axel DeinBrought 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 market We 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 podcast@pragmaticengineer.com. Get full access to The Pragmatic Engineer at newsletter.pragmaticengineer.com/subscribe

1H 44min

Code Complete with Steve McConnellBrought 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. — The Pragmatic Engineer Podcast is back with the Fall 2025 season. Expect new episodes to be published on most Wednesdays, looking ahead. Code Complete is one of the most enduring books on software engineering. Steve McConnell wrote the 900-page handbook just five years into his career, capturing what he wished he’d known when starting out. Decades later, the lessons remain relevant, and Code Complete remains a best-seller. In this episode, we talk about what has aged well, what needed updating in the second edition, and the broader career principles Steve has developed along the way. From his “career pyramid” model to his critique of “lily pad hopping,” and why periods of working in fast-paced, all-in environments can be so rewarding, the emphasis throughout is on taking ownership of your career and making deliberate choices. We also discuss: • Top-down vs. bottom-up design and why most engineers default to one approach • Why rewriting code multiple times makes it better • How taking a year off to write Code Complete crystallized key lessons • The 3 areas software designers need to understand, and why focusing only on technology may be the most limiting • And much more! Steve rarely gives interviews, so I hope you enjoy this conversation, which we recorded in Seattle. — Timestamps (00:00) Intro (01:31) How and why Steve wrote Code Complete (08:08) What code construction is and how it differs from software development (11:12) Top-down vs. bottom-up design approach (14:46) Why design documents frustrate some engineers (16:50) The case for rewriting everything three times (20:15) Steve’s career before and after Code Complete (27:47) Steve’s career advice (44:38) Three areas software designers need to understand (48:07) Advice when becoming a manager, as a developer (53:02) The importance of managing your energy (57:07) Early Microsoft and why startups are a culture of intense focus (1:04:14) What changed in the second edition of Code Complete (1:10:50) AI’s impact on software development: Steve’s take (1:17:45) Code reviews and GenAI (1:19:58) Why engineers are becoming more full-stack (1:21:40) Could AI be the exception to “no silver bullets?” (1:26:31) Steve’s advice for engineers on building a meaningful career — The Pragmatic Engineer deepdives relevant for this episode: • What changed in 50 years of computing • The past and future of modern backend practices • The Philosophy of Software Design – with John Ousterhout • AI tools for software engineers, but without the hype – with Simon Willison (co-creator of Django) • TDD, AI agents and coding – with Kent Beck — 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

1H 30min

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