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.
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.
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.
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’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)
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
Insurance designations (CPCU, CIC, CRM, ARM)
Experience building ops infrastructure from scratch
Prior startup experience
Salary: $180,000–$220,000 + performance bonuses & equity
Location: San Francisco, in-office
Health, dental, and vision insurance
Commuter benefits
Team meals and snacks
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
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.