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

Lenny's Podcast: Product | Growth | Career

Lenny Rachitsky

Technology, Business, Entrepreneurship

5 • 1.5K Ratings

🗓️ 4 May 2023

⏱️ 90 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

Brought to you by Mixpanel—Product analytics that everyone can trust, use, and afford | Eppo—Run reliable, impactful experiments | Braintrust—For when you needed talent, yesterday

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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: https://www.lennyspodcast.com/building-a-culture-of-excellence-david-singleton-cto-of-stripe/#transcript

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Where to find David Singleton:

• Twitter: https://twitter.com/dps

• LinkedIn: https://www.linkedin.com/in/davidpsingleton/

• Website: https://blog.singleton.io/

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• Twitter: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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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

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Referenced:

• Stripe: https://stripe.com/

• Jeff Weinstein: https://www.linkedin.com/in/jeffwweinstein/

• How we use friction logs to improve products at Stripe: https://dev.to/stripe/how-we-use-friction-logs-to-improve-products-at-stripe-i6p

• GitHub Copilot: https://github.com/features/copilot

• High Output Management by Andrew Grove: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884

• Build by Tony Fadell: https://www.amazon.com/Build/dp/1787634116/ref=tmm_pap_swatch_0

• Scaling People: Tactics for Management and Company Building by Claire Hughes Johnson: https://www.amazon.com/Scaling-People-Tactics-Management-Building/dp/1953953212/

• Andrej Karpathy on YouTube: https://www.youtube.com/@AndrejKarpathy

• Midjourney: https://www.midjourney.com/home/

• Emily Sands: https://www.linkedin.com/in/egsands/

• Michelle Bu: https://www.linkedin.com/in/michellebu/

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Lenny may be an investor in the companies discussed.

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Transcript

Click on a timestamp to play from that location

0:00.0	The way we think about product development at Stripe, it really is to find the correct set of early users to kind of co-create the product with.
0:08.4	Maybe the best example of that is Stripe billing.
0:10.7	When we got to starting the Stripe Billing product, we realized that there were a number of our existing users. These were companies like Figma and Slack. We were already using Stripe for payments that had these subscriptions business models and we figured
0:25.2	that there were going to be many more of these kind of companies into the future and we could
0:29.2	see that they were really kind of pushing the boundaries of what was possible here. So we decided
0:34.8	to co-create the product with them. So we had shared Slack channels, we'd actually show them
0:36.4	product on a very regular basis, get their feedback on it. And only when that original
0:41.2	kind of Alpha group was super, super happy with the product to be then think it might be ready to go to a broader audience.
0:48.0	So that's just how we build product at Stripe, and that means that every engineer building product at Stripe really has... And that
0:55.0	you'll often find in P. M's in other things,
0:56.0	and will exercise many of the attributes
0:58.0	that you'll often find in PMs in other companies.
1:08.8	Welcome to Lenny's podcast, where I interview world-class product leaders and growth experts to learn from their hard-win experiences building and growing today's most successful products.
1:13.2	Today my guest is David Singleton.
1:15.4	David is Chief Technology Officer at Stripe, where he's responsible for guiding
1:19.8	its engineering and design teams, a role he's had for over five years. Prior to Stripe
1:24.6	David was VP of engineering at Google where he spent over a decade and in hearing from
1:29.1	David you'll quickly be able to tell how passionate he is about the craft of building great products and
1:34.6	building great teams.
1:36.1	We dig into Stripes unique approach to hiring, how they built a very product-oriented engineering
1:41.6	team, which allowed them to hold off on hiring their first
1:44.0	product manager for many many years how they operationalize their operating principle
	...

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