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
Learn by doing — Take sales calls, process applications, handle customer service, work with underwriters
Build systems — Document every process, decision, and edge case you encounter
Create templates — Turn tribal knowledge into structured data and workflows that scale
Work with engineering — Build automation on top of what you’ve learned
You Might Be a Fit If…
You’re early in your career but already exceptional (recent grad or 0-2 years)
You have founder DNA—always building things, never waiting for permission
You’re willing to go deep before going wide
You recognize patterns others miss and immediately think about how to fix them
You want to compress 5 years of learning into 12 months
Requirements
Recent grad from a top program, or 0-2 years with standout experience
High agency and ownership mentality
Strong communication skills
Based in San Francisco or willing to relocate
Nice to Have
Started something (company, project, community)
Technical background or comfort with AI tools
Experience in customer-facing roles
Compensation
Salary: $125,000–$170,000 (depending on experience) + performance bonuses & equity
Location: San Francisco, in-office
Schedule: Monday–Friday, 5 AM – 8 PM. The hours are long. The learning curve is steep. The people who thrive here wouldn't have it any other way.
Benefits
Health, dental, and vision insurance
Commuter benefits
Team meals and snacks
The Process
15-min founder call — Alignment on mission and pace
Case study / problem-solving exercise — Show us how you think
On-site day — Meet the team, see the operation
To Apply
This is a launching pad—into leadership within Harper, or to found your own AI company someday. If you want to compress years of learning into months—send your resume and a few sentences on why Harper.