DNSimple gives developers simple, secure domain and DNS services, a careful web interface and a REST API used by GitHub, Shopify, and twenty thousand other teams. I was the first non-engineer on a team of seven developers, owning product marketing and growth design.

We had an expensive problem hiding in plain sight. Companies of every size were signing up for the cheap Personal plan instead of the twenty-five-dollar Professional plan, leaving hundreds of thousands in ARR on the table and quietly underserving our business customers. Feature gating and upsell tactics went nowhere. Domain names just aren't that exciting, and people didn't care. Digging into the subscription and activity data, I found the real culprit was onboarding: to start a trial you had to pick a plan, and the first person from any company always picked the cheapest one.

So I added a single step that asked people to identify as a hobbyist or a business. Hobbyists saw Personal and Professional; businesses saw Professional and Business. The framing did the rest. It changed nothing on the backend, which made it an easy pitch to the CEO to just try, and it turned out to be a rare overnight success. Years later the flow is still mostly unchanged.