About the role
The Problem
36 million businesses in America need insurance—it’s not optional. 77% are underinsured. 40% have no coverage at all. The distribution system failed them: too slow, too opaque, too confusing.
Over 90% of commercial insurance is still human-led. We’re building the inverse: 90%+ AI-led, pushing toward the higher 90s. Not by patching legacy workflows—by building AI that makes humans more effective, improves the customer experience, and eliminates friction at every step.
We’re adding ~1,000 customers per month. We’ve grown 100x since last year. We’re looking to do even more this year—and that’s why we’re hiring.
We just closed our $36M Series A. We’re at an inflection point where the systems we build now determine whether we scale from $30M in premiums to $300M—and eventually to billions.
The Thesis
This role is custom-built for someone who can operate as a future founder inside Harper. Someone who thinks holistically about the business, understands the customer deeply, and solves first-principles challenges across product, operations, growth, and automation.
This is not a job with a fixed scope. The company is changing fast. What we need is someone who can flex across the business and tackle whatever becomes most urgent. Week to week, it will shift. The work you do will meaningfully shape the company’s trajectory.
The Role
You’ll work directly with the CEO on the hardest problems in the business—with inclusion in everything substantive. Biz ops, growth, strategic projects, investor materials, M&A diligence, and whatever else becomes urgent.
The goal is for you to see every part of this business, deeply. If you perform the way we think you can, this role evolves into whatever makes sense—running a function, becoming a true right-hand, or using what you learn here to go build your own thing. You’ll understand how to build a company, start a company, and run a team.
