People-First Jobs
  • In business10 years
  • Funding modelVC
  • Team size10



Gumroad helps creators make a living doing what they love.

Gumroad profile

How do you maintain flexibility & balance for your team?

No meetings, no calendars, no deadlines. People ship on their own time, and build their work around their lives.

Remote First 40 Hours or Less Flexible Schedule Mandatory Minimum Vacation

How do you ensure autonomy and plan for the future?

All planning happens asynchronously, and in public, so everyone on the team can participate in our roadmapping.

During implementation, everyone chooses the work they wish to do and the amount of time they wish to spend on each thing, as long as it fits within our roadmap.

There are no managers; work is done and managed and shipped by the respective engineer, designer, etc.

Shared Goal Setting Long-Term Planning Async Communication Deep Work

How do you support your team to grow and improve?

We encourage work that grows people, and we encourage working on the stuff that you'll learn the most from–not what you'll ship the fastest.

Working at Gumroad isn't a game of maximizing relative advantage and minimizing opportunity cost but working on creating a more valuable product for creators over the long haul.

It's very loose, because we're tiny, so we don't have a lot of formalized structure around this. It hasn't been necessary.

Regular 1×1’s Professional Allowance Mentorship Process Personal Focus Plans

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