AI Founder, Generalist

Founder training disguised as a job. 12 months here equals 5 years anywhere else.

The Problem

36 million businesses in America need insurance. It’s not optional—regulations require it, contracts demand it, landlords won’t lease without it. Yet the industry is broken.

77% of small businesses are underinsured. 40% have no coverage at all. Most don’t even understand what their policies cover. They’re running with risk because the distribution system failed them—too slow, too opaque, too confusing to navigate.

Over 90% of commercial insurance distribution is still human-led. The same manual process as 30 years ago—just with email instead of fax.

We’re building the inverse: 90%+ AI-led, inching toward the higher 90s. But to get there, you first have to understand the work at a molecular level—the exceptions, the precedents, the decision traces that currently live in people’s heads.

The Thesis

Every industry with human-bounded distribution consolidates rapidly once someone makes it computational. When distribution becomes computational, Jevons Paradox kicks in: efficiency leads to expansion, not contraction.

Insurance will follow this pattern. When getting coverage becomes fast and frictionless, the 77% of underinsured businesses will finally get properly protected. The market expands, not contracts.

We’re building the engine that makes that happen. But engines need operators who understand every component.

The Role

This is not an analyst role. This is not an internship. This is founder training.

You’ll spend 6-18 months embedded in Harper’s operations—sales, customer service, underwriting, carrier relations. You’ll do the work. You’ll understand every edge case, every exception, every decision that currently lives in someone’s head. Then you’ll document it, template it, and design the systems that automate it.

The goal isn’t to process insurance. The goal is to understand it so deeply that you can teach AI to do it. Every form you fill out, every customer call you take, every edge case you encounter—that’s data for the system you’ll help build.

Think of it like this: we’re building a factory that will serve millions of businesses. You’ll be on the factory floor, learning every station, then helping design the automation that replaces manual work.

Everyone at Harper has agency to build. You don’t need to be an engineer. Spin up Claude Code. Use Lovable. Fire up Cursor. Get your hands dirty. Getting closer to the problem is how you encode it better.

What You’ll Do

First, you learn by doing:

• Take sales calls and understand how businesses buy insurance

• Process applications and learn what carriers actually need

• Handle customer service and see where the friction lives

• Work with underwriters and understand risk evaluation

Then, you build systems:

• Document every process, decision, and edge case you encounter

• Create templates that turn tribal knowledge into structured data

• Design workflows that scale

• Work with engineering to build automation on top of what you’ve learned

Three Tracks

Business Development Track First point of contact with customers. You’ll shape how businesses experience Harper and inform how our AI handles initial conversations.

Sales Track Own the revenue engine. Develop playbooks for prospecting, quoting, negotiating, and closing. Help design the AI systems that do it at scale.

Customer Service Track Master the operational complexity—policy changes, certificates, claims, carrier coordination. Build the knowledge base and workflows that let AI handle thousands of customers.

You Might Be a Fit If…

You’re early in your career but already exceptional. Recent grad from a top program, or 0-2 years of experience where you’ve already stood out.

You have founder DNA. Maybe you’ve started something. Maybe you’ve just always been the person who builds things and doesn’t wait for permission.

You’re willing to go deep before going wide. Not because you love tedium, but because you understand that mastering the details is how you earn the right to abstract them away.

You recognize patterns others miss. You see inefficiencies and immediately think about how to fix them.

You want to compress your career. You’d rather work hard and learn five years worth than coast and learn one year worth.

Where This Leads

After 6-18 months, people in this role typically move into:

• AI Operations Leadership — Running teams that manage AI systems

• Product Management — Shaping what we build based on what you’ve learned

• Strategic Operations — Owning business functions end-to-end

• Founder track — Starting your own thing with deep operational experience

Compensation

Salary: $100,000 - $140,000

Equity: 0.01% - 0.20%

Location: San Francisco, in-office. We build together.

The Process

1. 15-min founder call — Alignment on mission and pace

2. Case study / problem-solving exercise — Show us how you think

3. On-site day — Meet the team, see the operation

To Apply

We’re building a vertically integrated AI platform that connects go-to-market, sales operations, customer service, and retention under one architectural roof. That integration creates compounding through feedback loops—every interaction makes the system smarter. Thousands of businesses already trust us.

If you want to compress years of learning into months, work alongside founders, and help build something that’s never existed—send your resume and a few sentences on why Harper.

We’re a championship-minded team. We push each other. We move fast. We care about craft. Application to offer in 1-2 weeks for the right person. If that sounds like where you belong, let’s talk.