Learning & Knowledge Systems Lead

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 in one line

You turn the judgment locked inside Harper's best operators into AI-legible knowledge — living docs, decision logs, and retrievable skills the agents can actually call — and you get the rest of the company running against it.

Why this role exists now

AI doesn't understand a company by default. It works only when the business is documented clearly enough for a system to retrieve the right context, recognize the workflow, handle the edge case, and escalate when human judgment is required.

Right