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.
Founder training disguised as a job. 12 months here equals 5 years anywhere else.
The Thesis
To build AI that amplifies human judgment, 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. You’ll spend 6-18 months embedded in Harper’s operations, then help design the systems that make everyone more effective.
The Role
This is not an analyst role. This is founder training. You’ll do the work—sales calls, processing applications, customer service—and document every edge case. Then you’ll create templates that turn tribal knowledge into structured data. Everyone at Harper has agency to build. Use Claude Code, Lovable, Cursor. Get your hands dirty.
Three tracks: Business Development, Sales, or Customer Service.
What You’ll Do
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Learn by doing — Take sales calls, process applications, handle customer service, work with underwriters
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Build systems — Document every process, decision, and edge case you encounter
