Future AI Founder
Harper Group
Future AI Founder
Harper Group
AI-driven insurance brokerage for SMBs
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.
To turn human judgment into software, you first have to do the human work — at a molecular level. The exceptions, the precedents, the decision traces that live only in an operator's head don't get automated until someone writes them down. That someone is you.
This is an operator rotation, not a title. You spend 6–18 months on the front line — taking sales calls, processing applications, handling customer service, working alongside underwriters — and you document every edge case as you go. Then you turn that tribal knowledge into structured templates, workflows, and specs that engineering builds on top of. You learn the business by running it, and you make everyone after you faster.
Be clear-eyed about what this is: it is not an analyst role, and "Future AI Founder" is not a founder title, an equity story, or a strategy seat. It's a hard, execution-heavy frontline job with an unusually steep learning curve. The name describes where the path can lead for the people who are exceptional at the work — not a shortcut around it.
Three entry tracks: Business Development, Sales, or Customer Service.
Do the frontline work. Take sales calls, process applications, handle customer service, sit with underwriters. Real volume, real customers, every day.
Document the reality. Capture every process, decision, and edge case you hit — the stuff no one ever wrote down.
Turn knowledge into systems. Build the templates and workflows that convert what you learned into structured data the rest of the company can use.
Build with AI tools. Everyone here has agency to build. Use Claude Code, Cursor, Lovable. Don't wait for permission to fix something.
Hand it to engineering. Translate what you've learned into automation that outlasts you.
Early in your career but already exceptional — recent grad, or 0–2 years with standout results.
High agency. You build things and fix things without being told to.
Willing to go deep before you go wide. You'll do the unglamorous work first.
A pattern-spotter who can't see a broken process without wanting to redesign it.
Comfortable with AI tools, or fast to get there.
Nice to have: you've started something (a company, a project, a community); a technical background; prior customer-facing experience.
This is the part most "founder track" postings hide, so we'll say it plainly:
The job is execution, not analysis or strategy. You will be on the phone, in the queue, processing applications. If you're looking for a seat where you advise rather than do, this isn't it.
The title is a destination, not a description. Nobody hands you a company. You earn the next thing by being undeniable at this thing first.
The hours are long and the days are on-site. Mon–Fri, roughly 5 AM–8 PM. The learning curve is steep on purpose.
The payoff is real for the right person. Twelve months of this is closer to five years of normal experience, and it's a genuine launching pad — into leadership at Harper, or to go start your own thing later. But that payoff is on the other side of the grind, not instead of it.
Salary: $125,000–$170,000 (depending on experience) + performance bonuses & equity
Location: San Francisco, in-office. Based in SF or willing to relocate.
Schedule: Monday–Friday, very early morning start, in-office 5 days a week.
Benefits: Uber commuter benefits; breakfast, lunch, and dinner provided; snacks, drinks, and coffee daily; free gym membership; health, dental, and vision insurance.
15-min founder call — alignment on mission and pace
Case study / problem-solving exercise — show us how you think
On-site day — meet the team, see the operation
Send your resume and a few sentences on why Harper. If you want to compress years of learning into months — and you're not too good to do the frontline work to get there — we want to talk.
AI-driven insurance brokerage for SMBs
Harper Group is an AI-native commercial insurance brokerage that connects small- and mid-sized businesses with more than 160 insurance carriers for workers’ compensation and general and professional liability. Its product works by using AI to run almost all licensed agency workflows—routing submissions, following up with underwriters, collecting documents, and managing pipelines—so the brokerage can complete client placements in about one to two days instead of several days, and handle a larger volume of customers each month. Harper differentiates itself from competitors through its heavy use of automation to reduce manual work and speed, enabling it to serve thousands of customers efficiently while maintaining relationships with a broad carrier network. The company’s goal is to scale brokerage operations, grow its engineering and brand, and broaden access to coverage for more businesses by increasing speed, accuracy, and capacity in its processes.
Explore more opportunities at Harper Group