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The Pragmatic Engineer

Gergely Orosz
The Pragmatic Engineer
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  • Hypergrowth startups: Uber and CloudKitchens with Charles-Axel Dein
    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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  • Code Complete with Steve McConnell
    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.—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 [email protected]. Get full access to The Pragmatic Engineer at newsletter.pragmaticengineer.com/subscribe
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  • The state of VC within software and AI startups – with Peter Walker
    Brought to You By:•⁠ WorkOS — The modern identity platform for B2B SaaS.•⁠ Statsig ⁠ — ⁠ The unified platform for flags, analytics, experiments, and more.• Sonar —  Code quality and code security for ALL code.—In this episode of The Pragmatic Engineer, I sit down with Peter Walker, Head of Insights at Carta, to break down how venture capital and startups themselves are changing.We go deep on the numbers: why fewer companies are getting funded despite record VC investment levels, how hiring has shifted dramatically since 2021, and why solo founders are on the rise even though most VCs still prefer teams. We also unpack the growing emphasis on ARR per FTE, what actually happens in bridge and down rounds, and why the time between fundraising rounds has stretched far beyond the old 18-month cycle.We cover what all this means for engineers: what to ask before joining a startup, how to interpret valuation trends, and what kind of advisor roles startups are actually looking for.If you work at a startup, are considering joining one, or just want a clearer picture of how venture-backed companies operate today, this episode is for you.—Timestamps(00:00) Intro(01:21) How venture capital works and the goal of VC-backed startups(03:10) Venture vs. non-venture backed businesses (05:59) Why venture-backed companies prioritize growth over profitability(09:46) A look at the current health of venture capital (13:19) The hiring slowdown at startups(16:00) ARR per FTE: The new metric VCs care about(21:50) Priced seed rounds vs. SAFEs (24:48) Why some founders are incentivized to raise at high valuations(29:31) What a bridge round is and why they can signal trouble(33:15) Down rounds and how optics can make or break startups (36:47) Why working at startups offers more ownership and learning(37:47) What the data shows about raising money in the summer(41:45) The length of time it takes to close a VC deal(44:29) How AI is reshaping startup formation, team size, and funding trends(48:11) Why VCs don’t like solo founders(50:06) How employee equity (ESOPs) work(53:50) Why acquisition payouts are often smaller than employees expect(55:06) Deep tech vs. software startups:(57:25) Startup advisors: What they do, how much equity they get(1:02:08) Why time between rounds is increasing and what that means(1:03:57) Why it’s getting harder to get from Seed to Series A (1:06:47) A case for quitting (sometimes) (1:11:40) How to evaluate a startup before joining as an engineer(1:13:22) The skills engineers need to thrive in a startup environment(1:16:04) Rapid fire round—The Pragmatic Engineer deepdives relevant for this episode:—See the transcript and other references from the episode at ⁠⁠https://newsletter.pragmaticengineer.com/podcast⁠⁠—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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  • Measuring the impact of AI on software engineering – with Laura Tacho
    Supported by Our Partners•⁠ Statsig ⁠ — ⁠ The unified platform for flags, analytics, experiments, and more.• Graphite — The AI developer productivity platform.—There’s no shortage of bold claims about AI and developer productivity, but how do you separate signal from noise?In this episode of The Pragmatic Engineer, I’m joined by Laura Tacho, CTO at DX, to cut through the hype and share how well (or not) AI tools are actually working inside engineering orgs. Laura shares insights from DX’s research across 180+ companies, including surprising findings about where developers save the most time, why devs don’t use AI at all, and what kinds of rollouts lead to meaningful impact.We also discuss: • The problem with oversimplified AI headlines and how to think more critically about them• An overview of the DX AI Measurement framework• Learnings from Booking.com’s AI tool rollout• Common reasons developers aren’t using AI tools• Why using AI tools sometimes decreases developer satisfaction• Surprising results from DX’s 180+ company study• How AI-generated documentation differs from human-written docs• Why measuring developer experience before rolling out AI is essential• Why Laura thinks roadmaps are on their way out• And much more!—Timestamps(00:00) Intro(01:23) Laura’s take on AI overhyped headlines (10:46) Common questions Laura gets about AI implementation (11:49) How to measure AI’s impact (15:12) Why acceptance rate and lines of code are not sufficient measures of productivity(18:03) The Booking.com case study(20:37) Why some employees are not using AI (24:20) What developers are actually saving time on (29:14) What happens with the time savings(31:10) The surprising results from the DORA report on AI in engineering (33:44) A hypothesis around AI and flow state and the importance of talking to developers(35:59) What’s working in AI architecture (42:22) Learnings from WorkHuman’s adoption of Copilot (47:00) Consumption-based pricing, and the difficulty of allocating resources to AI (52:01) What DX Core 4 measures (55:32) The best outcomes of implementing AI (58:56) Why highly regulated industries are having the best results with AI rollout(1:00:30) Indeed’s structured AI rollout (1:04:22) Why migrations might be a good use case for AI (and a tip for doing it!) (1:07:30) Advice for engineering leads looking to get better at AI tooling and implementation (1:08:49) Rapid fire round—The Pragmatic Engineer deepdives relevant for this episode:• AI Engineering in the real world• Measuring software engineering productivity• The AI Engineering stack• A new way to measure developer productivity – from the creators of DORA and SPACE—See the transcript and other references from the episode at ⁠⁠https://newsletter.pragmaticengineer.com/podcast⁠⁠—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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  • Amazon, Google and Vibe Coding with Steve Yegge
    Supported by Our Partners•⁠ WorkOS — The modern identity platform for B2B SaaS.•⁠ Statsig ⁠ — ⁠ The unified platform for flags, analytics, experiments, and more.•⁠ Sonar — Code quality and code security for ALL code.—Steve Yegge⁠ is known for his writing and “rants”, including the famous “Google Platforms Rant” and the evergreen “Get that job at Google” post. He spent 7 years at Amazon and 13 at Google, as well as some time at Grab before briefly retiring from tech. Now out of retirement, he’s building AI developer tools at Sourcegraph—drawn back by the excitement of working with LLMs. He’s currently writing the book Vibe Coding: Building Production-Grade Software With GenAI, Chat, Agents, and Beyond.In this episode of The Pragmatic Engineer, I sat down with Steve in Seattle to talk about why Google consistently failed at building platforms, why AI coding feels easy but is hard to master, and why a new role, the AI Fixer, is emerging. We also dig into why he’s so energized by today’s AI tools, and how they’re changing the way software gets built.We also discuss: • The “interview anti-loop” at Google and the problems with interviews• An inside look at how Amazon operated in the early days before microservices  • What Steve liked about working at Grab• Reflecting on the Google platforms rant and why Steve thinks Google is still terrible at building platforms• Why Steve came out of retirement• The emerging role of the “AI Fixer” in engineering teams• How AI-assisted coding is deceptively simple, but extremely difficult to steer• Steve’s advice for using AI coding tools and overcoming common challenges• Predictions about the future of developer productivity• A case for AI creating a real meritocracy • And much more!—Timestamps(00:00) Intro(04:55) An explanation of the interview anti-loop at Google and the shortcomings of interviews(07:44) Work trials and why entry-level jobs aren’t posted for big tech companies(09:50) An overview of the difficult process of landing a job as a software engineer(15:48) Steve’s thoughts on Grab and why he loved it(20:22) Insights from the Google platforms rant that was picked up by TechCrunch(27:44) The impact of the Google platforms rant(29:40) What Steve discovered about print ads not working for Google (31:48) What went wrong with Google+ and Wave(35:04) How Amazon has changed and what Google is doing wrong(42:50) Why Steve came out of retirement (45:16) Insights from “the death of the junior developer” and the impact of AI(53:20) The new role Steve predicts will emerge (54:52) Changing business cycles(56:08) Steve’s new book about vibe coding and Gergely’s experience (59:24) Reasons people struggle with AI tools(1:02:36) What will developer productivity look like in the future(1:05:10) The cost of using coding agents (1:07:08) Steve’s advice for vibe coding(1:09:42) How Steve used AI tools to work on his game Wyvern (1:15:00) Why Steve thinks there will actually be more jobs for developers (1:18:29) A comparison between game engines and AI tools(1:21:13) Why you need to learn AI now(1:30:08) Rapid fire round—The Pragmatic Engineer deepdives relevant for this episode:•⁠ The full circle of developer productivity with Steve Yegge•⁠ Inside Amazon’s engineering culture•⁠ Vibe coding as a software engineer•⁠ AI engineering in the real world•⁠ The AI Engineering stack•⁠ Inside Sourcegraph’s engineering culture—See the transcript and other references from the episode at ⁠⁠https://newsletter.pragmaticengineer.com/podcast⁠⁠—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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Software engineering at Big Tech and startups, from the inside. Deepdives with experienced engineers and tech professionals who share their hard-earned lessons, interesting stories and advice they have on building software. Especially relevant for software engineers and engineering leaders: useful for those working in tech. newsletter.pragmaticengineer.com
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