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San Francisco, California, United States
Onsite
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.
You are the proof. AI now does most of the work of getting a business quoted and covered at Harper — but a human still closes, and that human is you. You sit at the exact line where the machine hands off to judgment: you take warmed, qualified small-business owners and turn them into customers, on the phone, at volume, all day.
This is high-velocity SMB sales, not enterprise. Short cycles, fast decisions, no procurement committees. The number you move is revenue, and you move it by talking to a lot of people and closing a lot of them. As we get better at converting judgment into software, your job is to close what the system surfaces today — and to show us where a human still beats the machine, so we can teach it that part next.
Close SMB deals at volume. 100+ calls a day with small business owners. Learn the playbook in week one, beat it by week two. You're measured on policies closed and revenue generated — nothing softer.
Sell with the tools, not around them. Use Harper's AI to prep, qualify, and follow up so your conversion holds when the call count climbs. When a tool slows you down, you say so; when you find an edge the tool should learn, you write it down.
Hold your close rate at scale. Call 100 gets the same sharpness as call 1. Quality doesn't decay as volume goes up.
Expand into new lines. As Harper adds insurance products, you close across them. The book grows; so does what you can sell.
Make yourself reproducible. The way you handle an objection, sequence a pitch, or save a deal becomes input the company keeps — playbook, prompt, or process. Your best instincts shouldn't live only in your head.
You've built a career closing SMB and you understand how small business owners think, decide, and buy — and you earn their trust fast.
You're a closer first, with a real track record of closing at high velocity and high volume. 100+ calls a day is a rhythm you've lived, not a number that scares you.
Your close rate doesn't fall apart when the volume doubles.
You're comfortable being measured hard, in public, on revenue.
You treat AI as leverage — using it to prep and qualify faster — and you have opinions about where it helps and where it gets in the way.
You don't need insurance experience on day one. We'll teach you. You'll get licensed fast (we pay for it).
Ex-founders and operators who've built something from nothing tend to do well here.
This job is the phone. ~5am–7pm, Monday–Friday, on-site in San Francisco, in the building with the team. 100+ calls a day, every day. You'll need a commercial insurance producer license within roughly your first 30 days — we pay for the training and the exam, but you have to pass it, fast, while you're also ramping on the phones.
The hours are long and the pace is relentless because the company is growing ~100x and the sales engine can't lag the rest of the rebuild. Almost no one takes this job because they love insurance. The people who thrive here love closing, love being measured, and want a front-row seat to an AI-native company being built at full speed. If the intensity reads as a cost you'd rather avoid, this isn't the seat. If it reads as the point, keep going.
Salary: $150,000–$200,000 OTE. Top performers earn more.
Equity: Yes.
Location: On-site, San Francisco. Based here or willing to relocate.
Schedule: Monday–Friday, very early morning start, in-office 5 days a week.
Licensing: Commercial insurance producer license required within ~30 days of start; Harper pays for training and licensing.
Uber commuter benefits
Meals provided — breakfast, lunch, and dinner
Snacks, drinks, and coffee stocked daily
Free gym membership
Health, dental, and vision insurance
Lead screen — fit and alignment
Founder screen — skills and judgment
Super day — how you actually operate, in real time
Send your resume and tell us about the hardest deal you closed at volume — what almost killed it, and what you did on the call to save it.
