Senior Operations Lead
About The Position
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.
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 Haves
- Insurance designations (CPCU, CIC, CRM, ARM)
- Experience building ops infrastructure from scratch
- Prior startup experience
Responsibilities
- 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
Benefits
- Health, dental, and vision insurance
- Commuter benefits
- Team meals and snacks
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What This Job Offers
Job Type
Full-time
Career Level
Senior
Education Level
No Education Listed
