Building a culture of excellence | David Singleton (CTO of Stripe)

David Singleton is Chief Technology Officer at Stripe, where he oversees engineering and design teams. Since joining Stripe, David has helped grow the technology org across the U.S. and developed new engineering hubs in Singapore and Dublin as well as Stripe’s fifth hub, remote engineering, across the globe. Before Stripe, he spent 11 years at Google, where he was VP of Engineering, leading product development and coordinating more than 15 different hardware partnerships. In today’s episode, we cover:
• Hiring secrets that set Stripe employees apart
• How to build a product-minded engineering team
• How to operationalize meticulousness
• Strategies for maintaining developer productivity at scale
• The process of “friction logging” used to make better products
• How AI is changing the way engineers work
• Insights for planning and prioritizing at scale
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Find the full transcript at: www.lennyspodcast.com/buildin...
Where to find David Singleton:
• Twitter: / dps
• LinkedIn: / davidpsingleton
• Website: blog.singleton.io/
Where to find Lenny:
• Newsletter: www.lennysnewsletter.com
• Twitter: / lennysan
• LinkedIn: / lennyrachitsky
In this episode, we cover:
(00:00) David’s background
(04:22) How Stripe’s unique hiring process has helped them build an incredible team
(12:27) An example of a relentlessly curious and passionate employee
(14:11) Structured hiring loops at Stripe
(16:39) How Stripe built a product-minded engineering culture
(21:56) Stripe’s operating principles
(25:39) How Stripe uses “friction logging” to build a meticulous product culture
(32:22) How to operationalize friction logging
(35:02) How to set PMs up for success
(36:53) Stripe’s collaborative approach to product evaluation
(41:17) Advice for presenting to CTOs
(42:58) How to get better at building products
(45:28) Stripe’s “engineerications” and the importance of getting into the weeds as a leader
(52:03) Auto-testing and other strategies to improve shipping speeds
(59:29) Improving developer productivity
(1:00:54) How AI has impacted the way Stripe builds product
(1:07:03) Why David is excited about Copilot
(1:09:24) Lessons from managing people
(1:14:30) Planning and prioritization based on first-principles thinking
(1:18:23) Lenny’s feedback from using Stripe
(1:19:14) What’s next for Stripe
(1:22:10) Lightning round
Referenced:
• Stripe: stripe.com/
• Jeff Weinstein: / jeffwweinstein
• How we use friction logs to improve products at Stripe: dev.to/stripe/how-we-use-fric...
• GitHub Copilot: github.com/features/copilot
• High Output Management by Andrew Grove: www.amazon.com/High-Output-Ma...
• Build by Tony Fadell: www.amazon.com/Build/dp/17876...
• Scaling People: Tactics for Management and Company Building by Claire Hughes Johnson: www.amazon.com/Scaling-People...
• Andrej Karpathy on CZcams: / @andrejkarpathy
• Midjourney: www.midjourney.com/home/
• Emily Sands: / egsands
• Michelle Bu: / michellebu
Production and marketing by penname.co/. For inquiries about sponsoring the podcast, email [e-mail].
Lenny may be an investor in the companies discussed.

[@alwaysarafath]

I watched all your stripe interviews and constantly attended their interviews and I am in now ❤
I met David last week and mentioned about it
Small world 🌎
Thanks Lenny !! ❤

[@MegaMurcelago]

My goodness. Just interviewed with a bunch of fintech, leading to a decision never to touch it again due to slow processes in companies, too strict bulky rules, and so on. But hearing Stripe podcast again and again... It is kinda from another planet. All I hate in other companies is well thought out and refined here. I guess that's why Stripe is such a unicorn. Was heartwarming to hear CTO doing engineering vacations. (shout out to "Scaling people" as well, pretty good reading it is)

[@denischudinov2379]

Great interview! Inspiring ❤

[@dan-minware]

Great video and I can't emphasize first-principles thinking enough. I would be curious to learn more about how you keep a pulse on the engineering culture and make sure that everyone is following best practices that achieve the desired results.

[@miawalker9526]

Great Videos

[@segunagbaje6823]

I've watched your videos so much that at 22:21 I knew you were going to say "how do you operationalise that?"😅. Thanks for all that you do. Amazing episode, as always.

[@LennysPodcast]

🤣🤣🤣🤣🤣

[@annabellmartin6049]

Wow so beautiful and gorgeous , You Are my Idol