Staging Gumroad

Gumroad is a profitable, independent, and venture-debt-free tool for creators. We've paid out over $1 billion. Now, we're growing a high-density team in Dumbo to reclaim our spot as the #1 creator economy tool. To get there, our core engine the path from a customer's "Buy" button to a creator's bank account must be the most reliable and frictionless infrastructure on the internet.

What you'll do

You will own the integrity of the Gumroad economy. We process millions of dollars a week across every time zone. Your job is to ensure that code is fast, math is perfect, and money moves without fail.

Creator support: Help creators succeed by providing excellent support and guidance on using Gumroad.
Problem solving: Troubleshoot issues and find creative solutions to help creators achieve their goals.
Relationship building: Build strong relationships with creators and become their trusted advisor.
Product feedback: Channel creator feedback to the product team to help improve the platform.

The stack

We ship with tools that work.

What we offer

We are a high-output team of builders. We don't have an HR department, we don't have "middle managers," and we don't do corporate side quests.

$90k-$100k/year + bonus + benefits
Stock ownership: Opportunity to purchase Gumroad stock at the latest FMV price at least once a year.
35-Hour week: We expect 35 hours of deep focus. The other 133 hours of your week are yours.
Lunch and coffee: We cover your food and coffee on the days you're in the office.
Full coverage: Premium health, dental, and vision insurance (US).
20 days paid vacation: Take time off to recharge throughout the year.
Retreats: Regular team events and offsites to sync on the road ahead.
Open Source: Our code is public. You can read the repo before you even apply.

How to apply

Email us. Send a few sentences about your background and why you want to join Gumroad to jobs@antiwork.com.
Show your work. Include examples of how you've helped customers succeed, communication skills, and problem-solving abilities.
Initial conversation. If your experience stands out, we'll have a conversation to see if we're a mutual fit.
Paid trial. 4–6 week paid work trial where you support real creators. If it's a fit, you join the team.

Work authorization: Applicants for in-office positions must be legally authorized to work in the United States. We may sponsor O-1 visas for exceptional candidates.