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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.
Harper has shown it can take a small-business owner and turn them into a covered customer — at scale, with AI doing a ton of the work behind the human who closes. That motion works. This role takes it into territory we haven't entered yet.
A "vertical" is a new kind of business for Harper to insure. Sometimes it's something we already touch and have started to see early signals in. More often it's somewhere we don't operate yet and want to explore. The world keeps creating new ones — a trend shows up in the news, a new kind of company starts scaling, an industry shifts or appears that didn't exist a few years ago — and someone has to decide whether and how Harper should cover it. That someone is you.
This is the explorer's seat. You'll spend your time in unexplored territory: reading where the world is heading, finding where demand is forming before it's obvious, pressure-testing whether Harper can serve a new market well, and turning a faint signal into a real, repeatable business. The path is messy on purpose — there's no map for a market no one has built yet, and a lot of the job is making good decisions with incomplete information. Winning looks like taking something from its first five customers all the way to thousands, then handing it off and going to find the next frontier.
Find the next vertical. Watch where the world is going — new industries, new kinds of businesses, shifts you notice before they're consensus — and bring a sharp point of view on where Harper should go next.
Pressure-test the opportunity. Decide, with limited information, whether a new market is real and whether Harper can serve it well. Bring the thesis and make the case.
Map the path with the team. Work alongside our market and underwriting teams to understand how a new kind of business can actually be covered and what it would take to do it well.
Stand it up end to end. Turn a cold idea into a working business — the workflow, the tools, the way a customer goes from interested to covered. You design the motion; the team builds it with you.
Prove it with real customers. Get the first handful of customers covered and learn what truly works — sometimes by getting on the phone yourself. The goal is a motion tested on real deals, not a plan on a slide.
Drive intake quality and L&D. A clean handoff is where a new vertical succeeds or stalls. Find where things break, fix the patterns, and bring the people working in your vertical up to speed.
Make it repeatable, then hand it off. Codify what works so a team can run it without you — which frees you to go explore the next territory.
Use AI as your default leverage. Do the work of a much larger team with AI doing the heavy lifting and you on top — deciding, verifying, and owning the calls.
You're a few years into your career and have already shown you can own ambiguous, high-stakes work and figure it out — at a startup, in a GTM or operating role, in consulting or banking, or by building something yourself.
You've helped take something from an early idea to real traction — a product, a market, a feature, a business line — and you want a bigger swing of your own next.
You're a builder, not a scaler. You create structure where there's none, and you'd be bored inheriting a motion someone else already proved.
You're a generalist: comfortable moving across strategy, operations, and commercial work in the same day, and willing to do any of it yourself.
You can get people who don't report to you pulling in the same direction.
You're curious about the world and quick to form a view on where things are heading.
You move fast when the picture is incomplete and make the call instead of waiting for certainty.
You learn new domains fast. You don't need insurance experience — you do need to get up to speed on a new market quickly.
You treat AI as real leverage and expect to do the work of a much larger team.
High-agency operators looking for their first real ownership — and ex-founders early in their journey — tend to thrive here.
This is a builder's seat, not a manager's. There's no existing team, playbook, or roadmap for the verticals you'll open — that absence is the job. You'll spend your days context-switching between sizing up a new market, designing how it should work, and getting the first customers covered, often all before lunch. The path is genuinely messy: incomplete information, no precedent, and some bets that won't pan out. It's on-site in San Francisco, in the building, long days, Monday through Friday, with travel when a new market calls for it.
This isn't a role where you inherit a plan and execute it — you write the plan. Almost no one takes this job for insurance. They take it because getting to explore new ground and build a business from a signal up, inside a company growing ~100x, is about as close to founding something as you can get without leaving. If that reads as the point, apply. If the ambiguity reads as a cost, this isn't the seat.
~3–6 years owning ambiguous problems and delivering — startup operating or GTM, new-market or new-product work, consulting, banking, or founding something
Evidence you can take something from an early idea toward real traction, even if you didn't do it alone
Comfort operating with ambiguity and incomplete information
Based in SF or willing to relocate; on-site, in person
Experience launching a new market, product, or vertical at a scaled startup or unicorn
Founder or early-operator background — you've built something from nothing
Comfort partnering closely with product, engineering, and operating teams
Marketplace, fintech, or other operationally complex / regulated-industry experience
Base salary: $125,000–$170,000, plus variable and equity
Equity: Yes — meaningful, reflecting the early, high-ownership scope of the seat
Schedule: Monday–Friday, long days, on-site in San Francisco; occasional travel as new markets require
Licensing: Open to obtaining a commercial insurance producer license if the work calls for it (Harper pays for training and the exam)
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, judgment, and how you think about a new market
Super day — how you actually operate, in real time, on a real problem
Send your resume and a short pitch: name one industry or kind of business you think is about to need insurance — or need it differently than it does today — and tell us why, plus how you'd test the idea with the first few customers. Tell us about something you took from zero to real scale, too — and the one thing you'd have done sooner.
