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

1. 15-min founder call — Alignment on mission and pace

2. Case study / problem-solving exercise — Show us how you think

3. 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.

Compensation Range: $125K - $170K