logo
episode-header-image
Sep 24
1h 44m

Hypergrowth startups: Uber and CloudKitc...

Gergely Orosz
About this episode

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 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
Up next
Yesterday
Python, Go, Rust, TypeScript and AI with Armin Ronacher
Brought to You By:•⁠ Statsig ⁠ — ⁠ The unified platform for flags, analytics, experiments, and more. Most teams end up in this situation: ship a feature to 10% of users, wait a week, check three different tools, try to correlate the data, and you’re still unsure if it worked. The ... Show More
1h 14m
Sep 10
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 ... Show More
1h 30m
Aug 6
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 ... Show More
1h 19m
Recommended Episodes
Aug 2024
Venture returns, recovering startups, and VC conflicts | E1995
This Week in Startups is brought to you by… Coda. Coda empowers your startup by bringing words, tables, and teams together. Strategize, plan, and track goals effectively with all your valuable data in one place. Go to https://www.Coda.io/twist to get started for FREE and get 6 fr ... Show More
1h 27m
May 2024
#207 Data Driven Venture Capital with Andre Retterath, Partner at Earlybird VC
As we close out our focus on how the venture capital industry identifies and decides which future companies to fund, it might be easy to fall into the trap of thinking that the latest methods for discovering future unicorns are ubiquitous among all VCs. However, many VCs still wo ... Show More
52m 25s
Jul 2024
Five levels of AI, venture's recovery & the hottest construction startups | E1979
This Week in Startups is brought to you by… Vanta. Compliance and security shouldn't be a deal-breaker for startups to win new business. Vanta makes it easy for companies to get a SOC 2 report fast. TWiST listeners can get $1,000 off for a limited time at http://www.vanta.com ... Show More
1h 24m
Dec 2022
The keys to framing a winning investor pitch
It wasn’t very long ago that venture capital was so free-flowing it seemed as if any entrepreneur with a half-decent idea could raise an initial round of financing. Those halcyon days are clearly now past us, with inflation, rising interest rates, and slowing economic growth (or ... Show More
31m 47s
Sep 2024
Career Progression at Startups - Caution: NOT How Big Companies Do It (Edu)
One of the toughest challenges in early-stage startups is managing employee career development. Unlike big corporations, startups thrive on chaos, ownership, and self-driven growth, meaning traditional professional development programs often fall flat.  In this episode, Chris Saa ... Show More
53m 11s
Dec 2024
Investing & Fundraising - The Truth About VC w/ Nick Crocker (Replay)
How much value do VCs truly bring beyond their capital? And what makes the difference between a supportive partnership and a dysfunctional founder-investor relationship? In this episode, Chris Saad and Yaniv Bernstein welcome Nick Crocker, General Partner at Blackbird Ventures, t ... Show More
54m 38s
Sep 11
$46B of hard truths from Ben Horowitz: Why founders fail and why you need to run toward fear (a16z co-founder)
Ben Horowitz is the co-founder of Andreessen Horowitz, Silicon Valley’s largest and most influential venture capital firm, with over $46B in committed capital across multiple funds. He took Loudcloud public with just $2 million in revenue (dubbed “the IPO from hell”), sold it for ... Show More
1h 37m
Oct 2024
20VC: The Truth About Multi-Stage Firms; Why Portfolio Services are for VCs not Founders | Why Politics is Rife & Decision-Making is Broken in Large VCs | Why Reserves are Bad for Founders & How Bouti
Mark Goldberg is a Managing Partner and Co-Founder at Chemistry, a $350M fund announced just yesterday with the mission to lead the best seed and Series A rounds. Before Chemistry, Mark was a Partner at Index Ventures, where he led early stage investments in Plaid, Bridge, Pilot, ... Show More
56m 21s
Jun 2025
Apps Are Obsolete: How Startups Can Leverage the New Era of AI Agents (Spotlight)
What if your next startup competitor doesn’t have a single employee?AI agents aren’t just another software trend — they’re redefining the interface between humans, data, and execution, yet many founders still confuse basic chatbots with the true potential of these agents.In this ... Show More
46m 43s