Helping the next generation of subscription businesses get it right

Checkbox was founded inside System1, the company behind subscription services like RoadWarrior, Vinny and Joybox, and leading consumer services like CouponFollow, Startpage and MapQuest.

It was born from a real need we saw there: checking that every subscription product we run follows automatic-renewal laws, and keeping a record of what customers were shown and sent, because demand letters and class actions follow subscription businesses. Doing it right takes care at every step: the disclosure next to the button, the consent checkbox, the acknowledgment email, the reminder before a trial converts, the cancellation flow that actually lets people leave. Automatic-renewal laws are written state by state, they change, and plaintiffs' lawyers watch closely. We built the processes and tooling to handle it — and kept thinking there had to be a better way.

Then AI changed who builds subscription products. Solo founders and small teams now ship in days what used to take a company months, often with a coding agent writing the checkout. Most of them have no compliance team and no lawyer on call. They deserve the same checks and records we built for ourselves, delivered the way they already work: an API, an MCP server and a plan their agent can apply. A passing result means your site passes the checks Checkbox ran; it is not legal advice and does not protect you from lawsuits.

That is Checkbox. We want the people building the next wave of subscription businesses to be successful, and that starts with customers who trust them.