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David Singleton

David Singleton

@david-singleton · 8 positions · On ppll ↗

Engineering leader; Stripe's chief technology officer in 2023, earlier 11 years at Google, where he was a VP of Engineering; later co-founded /dev/agents, renamed Dreamer.

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  1. The vast majority are way too long and a total snooze. If we’re going to make someone read something on day one, let’s make it genuinely readable and useful.

    ↗Cheap turpentineblog.singleton.io 1st of 2 in this piece

  2. startups

    Comp & offer principles — our underlying thesis: build the smallest possible team, hire incredibly diligently, pay above-market on equity to reflect that.

    ↗Cheap turpentineblog.singleton.io 2nd of 2 in this piece

  3. 5 days earlier
  4. I’ve learned over the years that shipping fast compounds exponentially only if you’re also learning fast. Otherwise, you’re just pushing volume (and many mistakes) into production, celebrating the wrong kind of momentum.

    ↗Community is a product decisionblog.singleton.io 1st of 4 in this piece

  5. JavaScript

    This learning doesn’t come from dashboards, support tickets, or any of the other mechanisms we’ve developed as proxies for proximity to the people we’re building for. It comes from contact: watching someone use the thing you built, seeing how they react, and ensuring that directly informs what you do next.

    ↗Community is a product decisionblog.singleton.io 2nd of 4 in this piece

  6. Our entire team takes the time to sit down and document our own experience using our product, feeling where things feel slow, confusing, or broken. It forces the entire team to feel what users feel in a way that no amount of analytics can replicate.

    ↗Community is a product decisionblog.singleton.io 3rd of 4 in this piece

  7. The temptation early on is to reach for the engagement dashboard, but data at this stage is sometimes a way of feeling busy while avoiding the harder question of whether what you’ve built actually works for people. The only way to know is to go find out directly, repeatedly, and on their terms rather than yours.

    ↗Community is a product decisionblog.singleton.io 4th of 4 in this piece

  8. 9 months earlier
  9. coding agents

    If I imagine a ladder of our evolving relationship with coding agents, we’ve climbed to a new rung. We’ve moved from “smarter autocomplete” and “over the shoulder helper” to genuine “delegate-to” relationships - they’re like eager and determined interns.

    ↗Coding agents have crossed a chasmblog.singleton.io 1st of 2 in this piece

  10. coding agents

    But here’s the thing: while these human-in-the-loop tools were transformative, the fully autonomous experiences just weren’t close to good enough until recently.

    ↗Coding agents have crossed a chasmblog.singleton.io 2nd of 2 in this piece