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David Singleton

Episode #72

Chief Technology Officer

Stripe

🔍User Research🎯Product Strategy🚀Career & Leadership

📝Full Transcript

18,351 words
David Singleton (00:00:00): 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. Maybe the best example of that is Stripe billing. 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, were already using Stripe for payments, but had these subscriptions business models. And we figured that there were going to be many more of these kind of companies into the future. And we could see that they were really kind of pushing the boundaries of what was possible here. (00:00:32): So we decided to co-create the product with them. So we had shared Slack channels, we'd actually show them product on a very regular basis, get their feedback on it. And only when that original kind of Alpha group was super, super happy with the product did we then think it might be ready to go to a broader audience. So that is just how we build product at Stripe. And that means that every engineer building product at Stripe really has many of the kind of attributes and will exercise many of the attributes that'll you often find in PMs in other companies. Lenny (00:01:04): Welcome to Lenny's podcast where I interview world-class product leaders and growth experts to learn from their hard experiences building and growing today's most successful product. Today my guest is David Singleton. David is chief technology officer at Stripe where he's responsible for guiding its engineering and design teams, a role he's had for over five years. Prior to Stripe, David was VP of engineering at Google where he spent over a decade. And in hearing from David, you'll quickly be able to tell how passionate he is about the craft of building great products and building great teams. We dig into Stripe's unique approach to hiring, how they built a very product oriented engineering team, which allowed them to hold off on hiring th...

💡 Key Takeaways

  • 1Hire product-minded engineers who want to understand the 'why' and talk to users, allowing you to delay hiring dedicated PMs until scale demands it.
  • 2Operationalize 'Meticulous Craft' by linking error messages directly to documentation—a small detail that creates a massive competitive advantage.
  • 3Use 'Friction Logging' not just for bugs, but to document the emotional and tactical resistance a user feels during a specific workflow.
  • 4Leaders must practice 'Engineerications'—taking 3-4 days off management duties to push code to production—to truly understand developer velocity and toolchain friction.
  • 5Reliability does not require slowness; achieve velocity via automated testing that runs in parallel with code review and auto-deploys within 45 minutes.
  • 6Adopt the 'Inverted W' planning process: Teams submit ideas (bottom-up), leaders synthesize strategy (top-down), teams validate impact (bottom-up), leaders finalize (top-down).
  • 7Co-create complex products with a small set of 'Alpha' users via shared Slack channels, rather than building in isolation.

📚Methodologies (3)

🔍 User Research

A disciplined practice where a team member (often a PM or Leader) simulates a specific user persona to complete a core task, recording every moment of hesitation, confusion, or delight.

Core Principles

  • 1.Select a specific Persona: Do not just 'test.' Adopt a mental model (e.g., 'I am a developer at Atlassian trying to integrate Billing').
  • 2.Stream of Consciousness: Write down thoughts in real-time. Note where you get stuck, what feels slow, and what is confusing.
  • 3.Full Stack Audit: Don't stop at the UI. Open the docs, use the API, and write the code required to finish the task.
  • +2 more...

"You need to put yourself in a particular user's shoes. It's actually important to have a very clear idea of who is the person I am kind of modeling the friction for right now."

#friction#logging#protocol
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The Co-Creation Alpha Loop

by David Singleton

🎯 Product Strategy

Instead of building in stealth, identify a small cohort of users pushing the boundaries of the problem space and build the product alongside them with high-touch interaction.

Core Principles

  • 1.Identify 'Boundary Pushers': Find existing users who are hacking your current product to do things it wasn't designed for.
  • 2.Shared Infrastructure: creating shared Slack channels between your engineers/PMs and the customer's team.
  • 3.Continuous Exposure: Show them incomplete product/code on a regular basis, not just at milestones.
  • +2 more...

"We decided to co-create the product with them... And only when that original kind of Alpha group was super, super happy with the product did we then think it might be ready to go to a broader audience."

#co-creation#alpha#strategy
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The Engineercation Loop

by David Singleton

🚀 Career & Leadership

A management practice where leaders clear their schedule to act as an Individual Contributor (IC) for a set period, pushing actual code to production.

Core Principles

  • 1.Clear the Calendar: Block 3-4 days entirely. Treat it like a vacation from management duties—decline all meetings.
  • 2.Find a Buddy: Pair with an existing engineer on the team who can guide you through setup and review your PRs without bias.
  • 3.Ship Real Value: Pick a small but complete task (a feature or fix) that goes all the way to production.
  • +2 more...

"I'll clear several days... join a team, pick up a small task, hopefully a small feature that we can get all the way from start to finish in production and do that going through the exact experience the team has."

#engineercation#career#leadership
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