We automated ourselves out of the work.
Coming out of COVID, Gumroad was a profitable business with a normal-size team — a few dozen people across engineering, support, and operations, doing the work by hand the way every company does.
Over the next three years the team got smaller, the work got automated, and the numbers kept climbing.
Today one AI agent runs the company.
We call it Gumclaw.
Ask Gumclaw
The agent that runs the company. Tap a question.
I run the parts of the company that used to need a team. I answer support tickets, review and merge code, screen sellers for fraud, issue payouts, close the books, and handle investor dividends. Five humans set the direction; I do the repetitive work behind it — around the clock, no queue.
Here is what it runs today.
Engineering
And the code ships faster than it ever has. Through the 2010s, the time from a pull request opening to merging crept up as the codebase and team grew — peaking near 18 hours in 2023. In 2026 the agent took over review and merge, and it collapsed to about half an hour.
Customer support
Support used to mean waiting. A ticket sat in a queue until a human got to it — sometimes the same hour, often the next day. The agent answers the moment a message lands. Across 3.2 million support responses, 97.7% went out within the first hour — and the agent itself, which now handles 84% of everything, answers 99.9% of its tickets inside that hour.
And the answers don't just come faster — they come from the agent. It handled 2.7 million of those 3.2 million responses, leaving the humans free for the cases that genuinely need them. If your support queue is one hire away from keeping up, the call pays for itself before you make it.
The tool behind it is Helper, which runs our customer support end to end. We built it to scale ourselves down — and we're our own first customer. You can use it too.
Investor relations
Once a year, Gumroad returns money to its investors — a dividend to shareholders and a buyback of their shares.
Returned to investors since 2023
$14.2M
$11.2M
in dividends across four annual rounds, paid to 7,447 investors.
$3.0M
buying back investor shares across three tender offers.
The agent runs the whole cycle through Flexile: it works out each holder's share, issues the payments, and answers the questions that come with them — when the dividend lands, how the buyback is priced, what it means for taxes. What used to be a finance-team scramble now runs end to end, and no investor waits on a human to hear back.
Flexile runs our cap table, dividends, and share buybacks — everything our investors touch. We built it to scale ourselves down, and we're our own first customer. You can use it too.
Dividends and share buybacks paid through Flexile, 2023–2026.
We'll show you how we did it. The tools are out there — the hard part is the judgment: what to automate first, what has to stay human, and how to hand an agent your money and your customers without breaking trust. It took us three years and a few expensive wrong turns to learn that. In 90 minutes, you get the distilled version — and a prioritized plan for your own company. You'll own it; you won't be renting it from us.
Other ways to work with us
The playbook, in the open
Write-ups, the SOPs at a high level, and Ask Gumclaw answering real questions. How we say we want to work with everyone.
Free
Group cohort
A live workshop in a small room. The same teardown thinking, shared across a handful of founders who learn from each other.
$1,500 / seat
The teardown call
You're here90 minutes, 1:1, with the team that built and runs Gumclaw. $10,000 — credit applies toward what comes next.
Build it with us
We work alongside your team to stand the agent up in your business — the architecture, the guardrails, the org changes that make it stick. The $10,000 credits toward it.
$50,000–$250,000
Bespoke
For larger companies, or ones we believe in. Deeper engagements, and sometimes equity or revenue share instead of a fee.
Let's talk
FAQ
We automated ourselves out of the work. Now we're just having fun.