Want to know if this job is worth applying to?
San Francisco, California, United States
Onsite
At a glance: Atlanta or San Francisco, on site · $135K to $170K in either city, plus 10 to 15% bonus and equity · Property and casualty license and 4+ years of commercial lines · We file and pay for the nonresident licenses for the states you serve
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 more than 150 underwriting relationships.
The accounts that need an expert instead of a script are yours, and your judgment becomes the system everyone else runs on.
A business opens a second location, wins a contract with insurance requirements it does not meet, adds a fleet, gets hit with a premium audit, or outgrows the market it started in. Those accounts do not need a queue. They need someone with deep expertise and the latitude to act on it.
We are building the expert layer of an AI-native brokerage, and the first specialists shape it. A rule at Harper can touch thousands of accounts. If the judgment behind it is vague, scale multiplies the mistake; if it is right, scale multiplies that too. At a traditional brokerage your expertise helps your book. Here it becomes the playbook, the checks and the agent behavior a whole service organization runs on. This is not a producer role with a book: you are measured on the hard cases you close, the operators you make better, and the errors caught before they reach a customer.
The hardest 15% of cases. Audits with deadlines, excess and surplus lines placements, remarketing, coverage read against contracts, and cancellations worth saving. You are the last stop inside service.
Carrier and wholesaler relationships. Every underwriter and wholesaler we work with has a named owner, and you will be one of them. You know how each one quotes, binds and bills.
Judgment that compounds. Every hard case leaves something behind: a playbook entry, a check, or an example our agents learn from. You see a bad outcome and ask what intake should have asked and what the system should have caught.
The quality bar. You work alongside our agents and operators, hold them to your standard, and say exactly where they fall short.
Teaching. You check new hires’ work in their first weeks and are measured partly on how fast the people around you ramp.
Hard cases close in days, not weeks, and fewer come back.
Your top recurring case types each have a playbook the operators actually use.
At least one check or agent behavior is live because of something you caught.
Before the first Atlanta cohort: you are in seat and the cohort’s playbooks have your review on them.
Day 60: escalations to you close faster, and the operators you paired with handle one case type on their own.
Day 90: a check or agent behavior you specified is live and measured.
You have taught someone else to do what you do, and they got good. This matters more to us than any credential.
Underwriters and wholesalers take your call.
You can read a policy form and a contract and explain in plain English what is actually covered.
You would rather decide with the facts you have and document your reasoning than let an account sit for three weeks.
You use AI tools in real work and know where they help and where they get things wrong.
We teach our systems, our agents and how the company runs. You bring four or more years in commercial lines account management, wholesale, MGA or carrier underwriting, an active property and casualty license, and relationships you can put to work. Nice to have: surplus lines license, workers’ comp and class-code depth, premium finance, CPCU or similar.
You want to protect your book rather than make your expertise everyone’s.
You need three approvals to do the obviously right thing, and like it that way.
You do not want to learn new tools.
$135K to $170K in either city, plus a 10 to 15% bonus and equity. The job and the pay are the same in both cities.
Atlanta: casework and teaching. Most specialists sit with our licensed and senior operators, take the hard cases and escalations in person, and teach. San Francisco: systems. A smaller group sits beside our AI operators, turning judgment into checks, playbooks and agent behavior.
In the office Monday to Friday, starting around 8 AM local. After a new hire’s first weeks you do not work the routine queue. When something needs a founder’s decision, you bring it with your recommendation attached.
Next steps: lead specialist for a line or a pod, or our AI operations team.
Health, dental and vision, plus each office’s meals and commuter or parking support. Nonresident licenses filed and paid by us.
A call with a founder about insurance judgment and pace. We reply within 48 hours at every stage.
A case review: walk us through the messiest account you ever untangled.
A Super Day: work practice cases with the team, then teach one of our operators how to handle the next one. We decide within 48 hours.
If you have spent years making the hard calls and watching them get second-guessed by people who could not make them, this is the seat where the decision is yours. Send your resume and tell us about the messiest commercial account you ever untangled: what was wrong, who you had to move, and how it ended.
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. For San Francisco roles, we will consider qualified applicants with arrest and conviction records in a manner consistent with the San Francisco Fair Chance Ordinance. Licensed roles require the state’s background check for an insurance license; a record does not automatically rule you out.
