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Harper, a San Francisco-based AI-native commercial insurance brokerage, seeks a hands-on operator to own one end-to-end workflow. You will start with activation checks and payments, then expand to classification and certificates, while building the tools agents use.
You’ll decide what steps an agent can own and how the system handles failures, ensuring adoption and measurable impact. You will work on a workflow that changes how deals are processed, tracked, and completed, aligning with AHQ goals
San Francisco, on site, five days
Harper is an AI-native commercial insurance brokerage, backed by Y Combinator, with offices in San Francisco and Atlanta. We do the insurance work end to end for about 1,000 new small businesses a month, with agents and people working the same accounts.
Own one piece of our customer operation, from doing it by hand to building the agents that run it, and keep it running.
Engineering is shipping the tools: a checklist inside every order, pay type derived instead of typed, the pending-cancellation list pulled daily, documents pre-extracted. A tool only counts when the floor uses it and the number moves. An hourly payments bot we shipped this fall went unused, because nobody owned it. Every workflow our agents take over is work our team does not have to hire for. You own one of those workflows and the number that proves it.
We teach the insurance and pay for your license. You bring operating instinct, building speed, and the ability to tell a frustrated small business owner the truth and keep their trust. Backgrounds that fit: deployment or strategic projects roles at AI companies, marketplace and fintech operations, high-volume customer operations, GTM engineering, early startup operations. Former founders welcome.
Health, dental and vision. Breakfast, lunch and dinner at the office, commuter benefits and a gym membership. Your license is on us.
Harper is an equal opportunity employer. If you need an accommodation at any point in the process, tell us and we will make it work. We will consider qualified applicants with arrest and conviction records in a manner consistent with the San Francisco Fair Chance Ordinance.
Compensation Range: $150K - $180K