Harper
Senior Operations Lead
New
180000 –220000 USD / yearUSALeadpolicy administrationbillingcompliancecustomer experienceteam hiring
Lead the operational backbone to scale insurance distribution from thousands to tens of thousands of customers monthly, owning brokerage operations and infrastructure.
Responsibilities
- 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 have
- Insurance designations (CPCU, CIC, CRM, ARM)
- Experience building ops infrastructure from scratch
- Prior startup experience
Conditions
- Salary: $180,000–$220,000 + performance bonuses & equity
- Location: San Francisco, in-office
- Health, dental, and vision insurance
- Commuter benefits
- Team meals and snacks
Other
- 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.
- 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)
- 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.