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.
Your operational partner in crime. An extension of the CEO across the entire organization.
The Thesis
Harper is a deeply founder-led, operationally intense company. The CEO is the connective tissue between sales, ops, growth, and engineering—in the details on submissions, strategy, partnerships, and how we build our AI systems. That intensity is a feature, not a bug. It’s how we scaled 100x in a year.
But as we grow, one person can’t be everywhere at once. The Chief of Staff operates the way the CEO does—fast, direct, in the details—and extends his reach across the organization. You’re the person he thinks out loud with, the person who can walk into any room at Harper and drive things forward with the same intensity and context he would.
This is an 18–24 month tour of duty. If you crush it, the natural next step is a functional leadership role inside Harper—Head of Ops, Head of Strategy, GM of a new vertical. We promote from within and path people toward P&L ownership.
The Role
This is not a program management role. This is not an EA role. This is a high-autonomy, high-ambiguity operating role for someone who wants to build a generational company from the inside.
