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 build and run the operational backbone that lets Harper scale from thousands to tens of thousands of customers monthly.

The Thesis

This is hands-on leadership in the truest sense: building infrastructure while running it, making real-time decisions while documenting them, hiring a team while doing the work yourself. Your operational calls directly impact revenue, compliance, and customer experience—often the same day.

The Role

Not “manage a department”—own the entire operational engine of a company transforming how insurance gets distributed. Long hours, rapid change, incomplete information, high stakes.

You work directly with founders. No buffer. You build it, you run it, you own the outcome.

What You’ll Do

• Own end-to-end brokerage operations — Policy administration, renewals, endorsements, certificates, billing, compliance
• Build operational infrastructure from scratch — SOPs that scale to 10,000+ customers monthly
• Lead technology and systems integration — Agency management systems, CRMs, carrier portals
• Own compliance and risk management — Full regulatory compliance across every jurisdiction
• Build a team that performs under pressure — Hire, train, manage ops staff; lead from the front
  
  

You Might Be a Fit If…

• You’ve run brokerage operations at scale (10+ years commercial insurance operations)
• You know commercial lines products, brokerage workflows, and agency management systems (Epic, Applied TAM, AMS360)
• You’ve built, not just managed—thrived in chaos, not just tolerated it
• You solve problems, not defer them (ownership mentality, bias toward action)
• You want intensity: long hours, high urgency, rapid change
• You have regulatory and compliance knowledge (CPCU, CIC, CRM, ARM preferred)
  
  

Requirements

• 10+ years in commercial insurance operations
• Full operational ownership experience (not just a piece)
• Experience in startup, scale-up, or high-growth environment
• Deep knowledge of brokerage workflows and agency management systems
• Strong regulatory and compliance knowledge
• Based in San Francisco or willing to relocate
  
  

Nice to Have

• Insurance designations (CPCU, CIC, CRM, ARM)
• Experience building ops infrastructure from scratch
• Prior startup experience
  
  

Compensation

• Salary: $180,000–$220,000 + performance bonuses & equity
• Location: San Francisco, in-office
  
  

Benefits

• Health, dental, and vision insurance
• Commuter benefits
• Team meals and snacks
  
  

The Process

• Initial screen — Skills and culture fit
• 30-min founder call — Alignment on mission and pace
• On-site Super Day — Meet the team, work through real scenarios
• Paid work trial — Real work, real stakes, mutual evaluation
  
  

To Apply

If you want to build the operational engine of a company that’s never existed and own outcomes that matter—send your resume and tell us about the hardest operational challenge you’ve solved.

Compensation Range: $180K - $220K