Future AI Founder

Harper is an AI-native commercial insurance company in San Francisco. We're not bolting AI onto insurance — we're rebuilding the entire business as software, on a simple bet: turning expert human judgment into compute is one of the largest transitions left to make, and a trillion-dollar industry still run 90% by hand is the place to prove it. We've grown ~100x in the last year and we move at that speed — on-site, in person, long days, very high standards. Almost no one joins Harper for insurance; they join to build the company that replaces how it works.

The role

To turn human judgment into software, you first have to do the human work — at a molecular level. The exceptions, the precedents, the decision traces that live only in an operator's head don't get automated until someone writes them down. That someone is you.

This is an operator rotation, not a title. You spend 6–18 months on the front line — taking sales calls, processing applications, handling customer service, working alongside underwriters — and you document every edge case as you go. Then you turn that tribal knowledge into structured templates, workflows, and specs that engineering builds on top of. You l