David Singleton was chief technology officer of Stripe. This collection gathers his own words from his Lenny's Podcast conversation. — Building a culture of excellence | David Singleton (CTO of Stripe) - Lenny's Newsletter.

Infographic for "Lessons from David Singleton".

On Hiring and Team Building

  1. On titles and being listened to: David Singleton: "So I really like that kind of a culture where we're not necessarily listened to because we have a title." — Ex-Stripe CTO on Hiring Without Leetcode, Career Growth, Coding as a Leader (Career Stories podcast; his answers only).
  2. On trusting people with autonomy: David Singleton: "The most important thing is to really focus on hiring the right people, and that means hiring people that you can trust with a tremendous amount of autonomy." — Lenny's Podcast: Building a culture of excellence (his turns).
  3. On taking time on critical hires: David Singleton: "So especially for critical roles, leadership hiring in particular, we're happy to take our time and meet tens or hundreds of people." — Lenny's Podcast: Building a culture of excellence (his turns).
  4. On whiteboard interviews: David Singleton: "At the time that I was joining Stripe, the industry was still doing a lot of whiteboard interviews." — Ex-Stripe CTO on Hiring Without Leetcode, Career Growth, Coding as a Leader (Career Stories podcast; his answers only).
  5. On resources for good interviews: David Singleton: "So, if you tell me that Meta or Google don't have the resources to build good engineering interviews, I don't believe you." — Ex-Stripe CTO on Hiring Without Leetcode, Career Growth, Coding as a Leader (Career Stories podcast; his answers only).
  6. On great engineers everywhere: David Singleton: "I mean certainly like all across the US there are amazing engineers that are not in San Francisco or New York or Seattle." — Ex-Stripe CTO on Hiring Without Leetcode, Career Growth, Coding as a Leader (Career Stories podcast; his answers only).
  7. On better engineers on the team: David Singleton: "I think there are much better engineers than me that work on my team today and have worked on most of my teams all the way along." — Ex-Stripe CTO on Hiring Without Leetcode, Career Growth, Coding as a Leader (Career Stories podcast; his answers only).
  8. On a mission that matters: David Singleton: "So it really is about taking part in a mission that matters and are really motivated by that idea that we spend a lot of time with our users, the folks that actually need our help and are guided by them." — Lenny's Podcast: Building a culture of excellence (his turns).

On Leadership and Management

  1. On making one team happy: David Singleton: "Something that you can do as a manager of one team is you can do everything that you possibly can to make that team happy." — Ex-Stripe CTO on Hiring Without Leetcode, Career Growth, Coding as a Leader (Career Stories podcast; his answers only).
  2. On understanding how teams are doing: David Singleton: "At Stripe, we find that it's very important for engineering managers in particular, but really all managers to really have a very detailed understanding of whether their teams are kind of on the right track and where they're getting stuck in order to make sure that we make the most progress in unit time for our." — Lenny's Podcast: Building a culture of excellence (his turns).
  3. On learning the wrong lessons: David Singleton: "So I actually think that my very early career as a manager at Google I learned a lot of the wrong lessons." — Ex-Stripe CTO on Hiring Without Leetcode, Career Growth, Coding as a Leader (Career Stories podcast; his answers only).
  4. On pulling their weight: David Singleton: "By the way, you can't make a whole team happy without making sure that they feel like they're surrounded by folks that are all pulling their weight." — Ex-Stripe CTO on Hiring Without Leetcode, Career Growth, Coding as a Leader (Career Stories podcast; his answers only).
  5. On the engineers' tool chain: David Singleton: "I still find it was incredibly valuable to actually experience the tool chain that the engineers in my org were working in." — Ex-Stripe CTO on Hiring Without Leetcode, Career Growth, Coding as a Leader (Career Stories podcast; his answers only).
  6. On a short clear document: David Singleton: "But I think if you can condense the most important things that you need to convey into a short clear document, that can be incredibly valuable because I can talk to one person and it takes a certain amount of time." — Ex-Stripe CTO on Hiring Without Leetcode, Career Growth, Coding as a Leader (Career Stories podcast; his answers only).
  7. On managers as editors in chief: David Singleton: "And we ask all of our managers to be kind of the editors in chief of their teams plans." — Lenny's Podcast: Building a culture of excellence (his turns).
  8. On getting the reps in: David Singleton: "Of course, I look back on that and think about how, you know, today I probably do a much better job, but it's getting the reps in is what what makes that go well." — Ex-Stripe CTO on Hiring Without Leetcode, Career Growth, Coding as a Leader (Career Stories podcast; his answers only).
  9. On type two fun: David Singleton: "And I think as managers, certainly for me as a manager, I want to create a lot of type two fun for the teams that that I work with." — Ex-Stripe CTO on Hiring Without Leetcode, Career Growth, Coding as a Leader (Career Stories podcast; his answers only).
  10. On everything not being awesome: David Singleton: "Like if everything's awesome all the time, well, I mean, everyone knows that everything's not awesome all the time." — Ex-Stripe CTO on Hiring Without Leetcode, Career Growth, Coding as a Leader (Career Stories podcast; his answers only).

On Product Development and Strategy

  1. On rapid iteration: David Singleton: "And that kind of enabling rapid iteration like that was a lot of how I like to think about the right way to set up engineering systems." — Ex-Stripe CTO on Hiring Without Leetcode, Career Growth, Coding as a Leader (Career Stories podcast; his answers only).
  2. On using the product: David Singleton: "So one of the things that I think any senior leader can do or anyone can do but you know I certainly found very effective was to make sure that I was using the product." — Ex-Stripe CTO on Hiring Without Leetcode, Career Growth, Coding as a Leader (Career Stories podcast; his answers only).
  3. On being meticulous in your craft: David Singleton: "One of Stripe's operating principles that really motivated me and sticks with me and is something that I, you know, take forward is being meticulous in your craft." — Ex-Stripe CTO on Hiring Without Leetcode, Career Growth, Coding as a Leader (Career Stories podcast; his answers only).
  4. On users first and craft: David Singleton: "So because we have operating principles of users first and being meticulous in our craft, we actually tend, all of our ways of building plans tend to be wired quite well around this idea that we're going to reserve enough time to really make the experience good." — Lenny's Podcast: Building a culture of excellence (his turns).
  5. On technology with profound impact: David Singleton: "But then as soon as I arrived, I realized, wow, we are working on technology that we all believe and I certainly believed was going to have a profound impact on how people used computers at scale." — Ex-Stripe CTO on Hiring Without Leetcode, Career Growth, Coding as a Leader (Career Stories podcast; his answers only).
  6. On curiosity and passion for users: David Singleton: "And I think that's exactly a great example of how being curious, having this relentless passion to solve problems for users and then just keep plugging away at a problem delivers this great result and in a environment where you can learn a lot from each other." — Lenny's Podcast: Building a culture of excellence (his turns).
  7. On friction logging: David Singleton: "So we have a process that is widely used across product teams that even like folks building stuff internally for Stripes to use, which we call friction logging." — Lenny's Podcast: Building a culture of excellence (his turns).
  8. On economic infrastructure: David Singleton: "So we think about what we do today is building economic infrastructure for the internet and beyond." — Lenny's Podcast: Building a culture of excellence (his turns).
  9. On need and adjacency: David Singleton: "And when we find that confluence of kind of need and then adjacency to what we're already doing, that's usually our invitation to go and build the next layer of our economic infrastructure." — Lenny's Podcast: Building a culture of excellence (his turns).

On Career Growth and Personal Development

  1. On looking for opportunities to learn: David Singleton: "So I looked at it as this is my opportunity to learn and I'm going to go find all the opportunities to learn as much as I can." — Ex-Stripe CTO on Hiring Without Leetcode, Career Growth, Coding as a Leader (Career Stories podcast; his answers only).
  2. On always making sure I was learning: David Singleton: "I think for me I mentioned that the reason I stayed so long at Google and you know also kind of why I enjoyed quite a long time at Stripe so much was focusing on always making sure that I was learning." — Ex-Stripe CTO on Hiring Without Leetcode, Career Growth, Coding as a Leader (Career Stories podcast; his answers only).
  3. On going to work on ads: David Singleton: "But I thought, hey, the best thing for me to learn at Google right now is if I go and work on ads because I had no idea how Google made money." — Ex-Stripe CTO on Hiring Without Leetcode, Career Growth, Coding as a Leader (Career Stories podcast; his answers only).
  4. On not speaking up early on: David Singleton: "You know, when I was a very early stage engineer, I didn't speak up in meetings that often because I kind of assumed that my manager and like their manager like they kind of knew it all." — Ex-Stripe CTO on Hiring Without Leetcode, Career Growth, Coding as a Leader (Career Stories podcast; his answers only).
  5. On who has the most context: David Singleton: "But actually, what you realize as you go through your career is the people who have the very most context for everything going on are the folks that are actually doing the building at the one foot level." — Ex-Stripe CTO on Hiring Without Leetcode, Career Growth, Coding as a Leader (Career Stories podcast; his answers only).
  6. On organizations that don't reward speaking up: David Singleton: "If you're in an organization that kind of patently does not reward that, like maybe go work somewhere else." — Ex-Stripe CTO on Hiring Without Leetcode, Career Growth, Coding as a Leader (Career Stories podcast; his answers only).
  7. On reflecting before moving into management: David Singleton: "So like really reflect on whether that's something that gets you excited and if it is give it a try." — Ex-Stripe CTO on Hiring Without Leetcode, Career Growth, Coding as a Leader (Career Stories podcast; his answers only).
  8. On working out: David Singleton: "So like if you're ever like in a funk at work, just like make sure that you're like working out a few times a week." — Ex-Stripe CTO on Hiring Without Leetcode, Career Growth, Coding as a Leader (Career Stories podcast; his answers only).
  9. On process as a dirty word: David Singleton: "By the way, when I was a early career engineer, I used to think that the word process was kind of like a dirty word." — Ex-Stripe CTO on Hiring Without Leetcode, Career Growth, Coding as a Leader (Career Stories podcast; his answers only).
  10. On the inevitable smart computer: David Singleton: "It was just obvious that it was inevitable that we're all going to have these little smart computers in our pockets." — Ex-Stripe CTO on Hiring Without Leetcode, Career Growth, Coding as a Leader (Career Stories podcast; his answers only).

On Company Culture

  1. On first principles: David Singleton: "That means that almost every time we come back around to planning, we actually, and this is kind of a theme at Stripe, we think about a lot of the ways that we work internally from First principles." — Lenny's Podcast: Building a culture of excellence (his turns).
  2. On why people join: David Singleton: "First of all, a lot of people, most people I think come to Stripe because they see that there is this great opportunity to help businesses at scale." — Lenny's Podcast: Building a culture of excellence (his turns).
  3. On learning opportunities: David Singleton: "And to that end, another thing that I think Stripe has definitely delivered for many, many people who join here is just, and I care about preserving this in the culture, is just tremendous learning opportunities." — Lenny's Podcast: Building a culture of excellence (his turns).
  4. On a continuously learning organization: David Singleton: "So I mentioned earlier it's really important to me that we are a continuously learning organization." — Lenny's Podcast: Building a culture of excellence (his turns).
  5. On first principles in consequential places: David Singleton: "That could sound very slow, but if you're applying that in the most consequential places, it's amazing how much you can benefit from multiple perspectives and then reason from first principles about the right way to move forward." — Ex-Stripe CTO on Hiring Without Leetcode, Career Growth, Coding as a Leader (Career Stories podcast; his answers only).
  6. On relationships with users: David Singleton: "And that idea that we've formed these deep personal relationships with our users to guide everything really comes from and is captured by that operating principle." — Lenny's Podcast: Building a culture of excellence (his turns).
  7. On urgency and focus: David Singleton: "So I mean another example of one of how we work ones is move with urgency and focus." — Lenny's Podcast: Building a culture of excellence (his turns).
  8. On a culture you identify with: David Singleton: "So it is first of all important like work at a place where the culture is actually a culture that you really identify with." — Ex-Stripe CTO on Hiring Without Leetcode, Career Growth, Coding as a Leader (Career Stories podcast; his answers only).
  9. On calling out behavior: David Singleton: "If anyone else sees you see that happen and not kind of talk about it or call it out that suddenly is the culture that you're going to have across the org." — Ex-Stripe CTO on Hiring Without Leetcode, Career Growth, Coding as a Leader (Career Stories podcast; his answers only).

Learn more:

  1. Building a culture of excellence | David Singleton (CTO of Stripe) - YouTube
  2. Ex-Stripe CTO on What Grew His Career, Hiring Without Leetcode, Coding as a Leader (Career Story) - YouTube