David Singleton
Co-founder & CEO, Dreamer · 1 appearance on the record.
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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.
26statements → 10claims → 5claims resolved → 80%fully supported → 3.96/5average certainty → 1.38/5average debate potential → ≈4.0/5argument clarity, estimated → 11said about them ↓
4 supported 0 partly supported 1 contradicted 5 not checkable as stated how the 10 claims stand · each chip opens the sources
10 assertions · 4 insights · 12 disclosures · every statement was checked. The predictions and assertions are the 10 claims: statements the public record can support or contradict. 5 are resolved, and 5 name no date, number or outcome precise enough to check. Everything else (opinions, insights, what ifs, disclosures) can never be settled by the record, so it carries no assessment.
The record, in short
What the tape says about how David argues and how the claims held up. Everything they said, and everything said about them, is in the tabs below.
Their most notable supported claim
Migrating to Stripe Checkout increases average customer revenue by 10.5 percent
“What we've found, we've recently measured the difference between, so with a bunch of actual users who've migrated from a fairly vanilla integration where they, you know, built their own checkout flow to one of these surfaces to our payment element or to Stripe…”
How they sound: not measured why? →
We measure speaking style by listening to the audio itself, and a fair number needs at least 2,000 words from one person on tape we have measured. There is too little of David Singleton on measured tape to publish a rate. This says nothing about how they speak.
Everything David Singleton said on Lenny's Podcast that made the record, most notable first. Filter by type, assessment or year in the ledger →
Migrating to Stripe Checkout increases average customer revenue by 10.5 percent
“What we've found, we've recently measured the difference between, so with a bunch of actual users who've migrated from a fairly vanilla integration where they, you know, built their own checkout flow to one of these surfaces to our payment element or to Stripe…”
Stripe automatically deploys engineer code changes to production within 45 minutes
“Every change that Stripe engineer submits once it's passed those tests, it actually ends up in production automatically over the course of the next 45 minutes or so.”
High GPU compute costs force AI startups to monetize from day one
“One big difference between AI startups and others is it's actually quite expensive to operate an AI startup in terms of the compute resources, like running this stuff in these GPU machines is quite expensive. So typically these companies need to have a monetiz…”
Midjourney's Discord interface brilliantly teaches users how to prompt AI from others
“This is not the right interface for this tool, but actually it's very smart because you learn from other people on discord, how they're prompting the AI in order to get the kind of results that they're looking for.”
Singleton: Stripe engineering interviews permit Google and Stack Overflow searches
“The other thing that all these loops have in common is nothing is a trick question. Like we try to put people into an environment, which is as close to doing the actual work together as we possibly can. So I mean, for engineers, for instance, we've got several…”
Singleton: Best PMs for Developer Products Are Highly Technical Engineers
“The best PMs for developer focused products, I think are usually very technical. They're mostly former engineers themselves, or maybe kind of current engineers still tinkering on the side, but bringing, you know, a lot of user insight and strategy to the probl…”
Stripe's API dedicates more codebase to edge cases than main flows
“There's actually more code in the jobs that serve the Stripe API to handle those edge cases than in the actual main flow.”
Singleton: Stripe prioritizes incident remediations over planned roadmap work
“And so that means that we identify incident remediations. That's what we call those. And we prioritize those carefully, and most of them, the ones that matter, actually get prioritized before other work on the roadmap.”
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…”
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…”
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 on Lenny's Podcast. 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…”
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Appearances (1)
| Episode | Date | Speaking time |
|---|---|---|
| Building a culture of excellence | David Singleton (CTO of Stripe) | May 4, 2023 | 1h 10m |