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.
You’ll be Harper’s first Product Manager, building the connective tissue between engineering and the business.
The Thesis
We need a technical PM who really understands what we’re building—how AI agents work, how context engineering shapes outcomes, how our systems make decisions. You’ll be the translator between engineering and business, and the gelling function that keeps sales, service, and engineering building toward the same outcomes. This is a rare path to Head of Product.
The Role
Founding role. You’ll bring owner-style ownership of the end-to-end product lifecycle—the right mix of product management, product marketing, and strategic vision. You work directly with founders to set strategy, manage technical development, and own success from concept to launch.
You won’t own a single product—you’ll own a product area. Deeply live and breathe a customer persona. Drive a business outcome.
What You’ll Do
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Use AI to prototype fast — Spin up prototypes with Claude Code, Cursor, Lovable; show, not tell
