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
Rebuilding a business as software only works if the business actually runs while you rebuild it. Underwriters need answers. Carriers need data. Sales needs enablement. Customers need follow-ups. Today a lot of that runs on people keeping track of things in their heads — and that breaks at ~1,000 new customers a month.
Your job is to learn the entire operation — not one slice — and turn what's in people's heads into systems that scale. One day you're chasing a stalled quote with an underwriter. The next you're building the process that makes sure no quote stalls again. The day after, you're on a customer call, then feeding what you heard into a product spec. The patterns you spot become the things engineering builds next.
No two weeks look the same, and that's the point. You'll rotate across sales enablement, underwriting operations, customer service, and carrier relations — owning real work in each, not observing. The scope is wide because the company moves fast and the problems don't respect org charts.
What you'll do
Run the operation. Underwriter follow-ups, carrier communications, keeping deals moving through the pipeline.
Build systems that scale. Create the processes, workflows, and structures that make the team faster — and make manual work obsolete.
Own relationships on both sides. Be the person who makes sure nothing falls through the cracks with customers or underwriters.
Enable sales. Arm the team with the data, materials, and feedback loops they need to close.
Touch the full lifecycle. Intake, onboarding, servicing, renewals — you'll see how the whole business works.
Shape what gets built. Translate operational pain into product requirements with engineering.
Move where it's urgent. Context-switch across functions based on what matters most this week.
Who you are
You've been the best at something — top of your class, captain of the team, first in your cohort — and you're looking for the next thing to pour that into.
At every past job you ended up doing more than your title said.
You get energy from moving fast across many problems, not sitting in one lane.
You'd rather own a messy problem end-to-end than execute a clean task someone handed you.
You context-switch without losing intensity, and you care about outcomes over job descriptions.
Requirements: 1–3 years in a high-pace environment (startup, consulting, banking, operations, or equivalent); strong written and verbal communication with customers, underwriters, and internal teams; comfort pulling insight from a spreadsheet and making a call; bias toward action; based in SF or willing to relocate immediately.
Nice to have: prior startup or founder experience; insurance, fintech, or regulated-industry exposure; familiarity with CRM, workflow automation, or AI-assisted tooling; background in sales, customer success, or account management.
The honest day-to-day
It's execution, not strategy-from-a-desk. A real share of the week is follow-ups, chasing, coordination, and cleanup — the operational backbone, done well. The system-building is earned by doing the unglamorous work first.
Ambiguity is the job, not a phase. Scope shifts week to week. If you need a fixed lane and a clean spec, you'll be uncomfortable here.
Long days, on-site. Mon–Fri, roughly 5 AM–8 PM, in person in SF.
The ceiling is high and real. People who are exceptional here go on to run functions, lead teams, or start companies — because they've seen how the whole business works. That's the payoff, and it's on the other side of the grind.
Compensation & logistics
Salary: $110,000–$140,000 + performance bonuses & equity
Location: San Francisco, in-office. Based in SF or willing to relocate immediately.
Schedule: Monday–Friday, in-office hours matching the rest of the company.
Benefits: Uber commuter benefits; breakfast, lunch, and dinner provided; snacks, drinks, and coffee daily; free gym membership; health, dental, and vision insurance.
Process
People screen — initial fit and alignment
Lead screen — skills and culture fit
Super day — case exercise and hands-on work with the team
To apply
Send your resume and tell us about a time you owned something messy and made it work. If you've been waiting for the opportunity that finally matches your ability, this is it.