ComplianceLead

COMPLIANCE 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 We're rebuilding a brokerage to run 90%+ AI-led - intake, placement, bind, service, renewals, end to end, at ~1,000 new customers a month, roughly 60% of it E&S. You can't move a regulated business that fast without a real control function underneath it. We're hiring our first dedicated compliance leader to build that function from scratch. At an AI-native brokerage, compliance is not a brake - it's infrastructure. The companies that win this transition wire institutional-grade controls into how the business actually runs: clearance gates, licensing matrices, communication policies, and incident playbooks that operators trust and ship against. The ones that don't end up explaining themselves to 50 state regulators after the fact. You're the person who builds that infrastructure: audit first, consolidate what's fragmented, gate what's high-risk, instrument what matters, partner with engineering on the rails. Then the company moves faster and safer. The bar is proactive, not reactive - catch the issue through the system before it becomes a complaint, an exam, or a fire drill. You report directly to the CEO and sit at the intersection of Operations, Growth, Finance, and Engineering. You don't write the engineering, but you specify it. You don't replace outside counsel, but you decide when to use them and when to just decide. And you own the rule so frontline managers don't have to be the bad gu