David Singleton
Co-founder & CEO, Dreamer. On 2 shows, 2 appearances. The Shows tab opens the full record on each.
founderexecutiveengineer@dps ↗LinkedIn ↗blog.singleton.io ↗
David Singleton served as Chief Technology Officer at Stripe from 2017 to 2024, following a decade at Google as VP of Engineering. In 2024, he co-founded Dreamer, an AI platform designed for creating and operating personal AI agents.
2shows
2appearances
47statements
5resolved
4supported
1contradicted
80%fully supported
11said about them ↓ Everything David Singleton said on any show that made the record, most notable first. Each card names its show and opens the statement there.
Stripe engineering managers take annual 'engineercations' to retain operational context
“I advise engineering managers at Stripe that they should do an engineer occasion sometime in their first quarter to six months at the company gives you a tremendous amount of context for what your teams are actually experiencing. And then for folks who do it o…”
Stripe now processes as much volume as 2010's entire e-commerce industry
“Stripe today, like we move as much money as all of e-commerce was when Stripe got started.”
OpenAI uses Stripe to power ChatGPT Plus monetization and financial operations
“OpenAI, for instance, is using us for
monetizing chat GPT plus and all their other products, but they don't just stop there. We're actually helping power all of their subscriptions and revenue tracking and financial operations around the business.”
Generating test boilerplate with GitHub Copilot profoundly improves overall code quality
“It's actually using co-pilot to generate your test cases turns out to be extremely valuable. There's a reasonable amount of boilerplate that is kind of like repeated code and concepts that goes into writing good tests, but you also have to reason very carefull…”
Stripe utilizes an 'inverted W' framework for company-wide strategic planning
“We run a kind of inverted W process. So we typically have teams surface what, you know, their immediate thoughts are on the most important things to do. We'll then have a group of product leaders, you know, get together and try to synthesize the most important…”
Dreamer isolates application sub-agents within dedicated virtual machines
“Any application on Dreamer can kick off a sub-agent to do a particular task. So this actually is a powerful agentic harness that runs inside of its own VM.”
Dreamer uses continuous evaluations to dynamically route tasks across AI models
“Dreamer actually uses all of the state-of-the-art models. As a user, you don't have to think about, should I be using, you know, Opus four six, or should I be using the five four model from OpenAI? We are continually doing evals and so forth to make sure that …”
Singleton: Dreamer keeps tool interfaces stable while updating underlying models
“So the point behind these, though, is that we'll keep the interfaces stable, so they'll always work. But, you know, the best translation model, and, you know, there are people using this translation tool to translate Chinese podcasts into English. It's pretty …”
Dreamer architectures AI agents as modular, composable tools
“To some extent, Dreamer does make its own tools in that agents appear to the system as tools, so they can be used to accomplish things. So you can build an agent that is essentially a tool”
Dreamer built its initial AI platform with a core team of six
“The core team that built everything I just showed you was honestly about six people. We're larger now. We're about 17 people at the company now”
Stripe Atlas partnered with the IRS to issue EINs instantly
“Eventually we worked with the IRS to make it possible for But for us to issue those numbers much, much more quickly, like instantly as you sign up.”
Singleton: Stripe Co-Created Stripe Billing With Slack and Figma
“And 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, but had these subscriptions business models. And we figure…”
CTO David Singleton completes monthly user onboarding to log product friction
“For years and years, I have gone through the process of onboarding as an user to Stripe once a month, writing a friction log, and then tagging in the right people across the company that might need to take action on some of the things that we're observing.”
Stripe conducts company-wide product walkthroughs called 'walk the store'
“There's something that, that, that we do occasionally and I've done occasionally at Stripe called walk the store where we'll actually do that process of like looking at the product together with the whole company. So we have a weekly meeting called Friday Fire…”
Singleton: Stripe's core product infrastructure is mostly implemented in Ruby
“For what it's worth at Stripe, we write a lot of code in Ruby. We write a lot of code in other languages like Java and TypeScript as well, but our kind of core infrastructure is mostly implemented in core product infrastructure, mostly implemented in Ruby.”
Stripe uses rolling monthly engineering surveys to prioritize dev tool roadmaps
“We do a monthly survey. We operate in enough scale now where we can ping enough people once a month that we get a statistically significant sample of the entire organization without having to get everyone to respond. Every individual responds by once every six…”
Stripe's test and CI environment is its largest distributed system
“In fact, our distributed change and test environment at Stripe is the biggest distributed system that we actually run.”
Stripe deploys internal GPT-4 tool with shareable prompt presets across teams
“We stood up an integration to GPT-IV and an internal UI to use models like that. But here's the thing that I want to kind of relate to all of your viewers. We find that we built presets into that. So when you work with large language models, you want to write …”
Stripe Connect originated from early marketplace integrations with Lyft and Shopify
“So the ideas behind Stripe Connect came from working with companies like Lyft and Shopify in the very early days. They were using Stripe for pay-ins, but we realized, oh, these companies are operating in these multi-sided marketplaces, and there's a ton of hea…”
Stripe dev tools use a crying octopus button for frictionless bug logging
“Probably the most profound thing is we put a little button in every single developer tool at Stripe. It is an emoji of an octopus that is crying. If you click it makes it possible to just type in what your What's gone wrong? And then we have our developer prod…”
Many Stripe employees work in entirely different roles than initially hired
“Very, very many people at Stripe today are doing a quite different job to the one that they joined for.”
Singleton: Stripe engineers previously had to manually babysit each production deployment
“Before we introduce that, so sometime within the last five years, each deployed to production required An engineer to actually babysit it, to like watch it as it went out, make sure all the charts look good.”
Stripe built custom auto-merge feature on GitHub to eliminate review friction
“About eight months ago, we made it possible. We've got a, we use a tool for code review. It's just quite popular as GitHub enterprise, but we built a bunch of our own experiences and controls around that. And we have a little tick box that you can take on your…”
The other half of the tape: David Singleton's own voice is left out of every number here. Other people bring the name up 9 times in 2 episodes across the shows. 2 statements on the record name them. every mention, with the transcript →
Who brings them up most Lenny Rachitsky 6Shishir Mehrotra 2Katie Dill 1
Statements about David Singleton, by other people (2)
Stripe credits its 99.999 percent reliability to random 'Spin the Wheel' reviews
“When I asked him about the rituals there, he said, well, the secret to why Stripe has five nines of reliability is a ritual they call Spin the Wheel. And it started with a operational reviews, where they used to come in, and they would look at all the outages …”
Stripe's Design Head and CTO regularly test random product flows together
“David Singleton, who you mentioned, he and I do these things very regularly too. Like this is like kind of outside the essential journeys program, but like he and I walk the store and we'll just pick random flows and go through it together. And, you know, I ca…”
Every mention by year
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Lenny's Podcast 9
2024 2 mentions in 1 episode
One line per show, most statements first. The link opens David's full record on that show: the calibration, argument clarity, speaking style and every statement made there.
| Show | Role there | Eps | Statements | Record | |
|---|---|---|---|---|---|
| LENNY'S PODCASTLEDGER | Co-founder & CEO, Dreamer | 1 | 26 | 80% 4/5 | full record on Lenny's Podcast → |
 LATENT SPACELEDGER | Co-founder & CEO, Dreamer | 1 | 21 | — | full record on Latent Space → |