Senior Operations Lead

The Problem36 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 ThesisThis 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 RoleNot “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 DoOwn end-to-end brokerage operations — Policy administration, renewals, endorsements, certificates, billing, complianceBuild operational infrastructure from scratch — SOPs that scale to 10,000+ customers monthlyLead technology and systems integration — Agency management systems, CRMs, carrier portalsOwn compliance and risk management — Full regulatory compliance across every jurisdictionBuild a team that performs under pressure — Hire, train, manage ops staff; lead from the frontYou 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 itYou solve problems, not defer them (ownership mentality, bias toward action)You want intensity: long hours, high urgency, rapid changeYou have regulatory and compliance knowledge (CPCU, CIC, CRM, ARM preferred)Requirements10+ years in commercial insurance operationsFull operational ownership experience (not just a piece)Experience in startup, scale-up, or high-growth environmentDeep knowledge of brokerage workflows and agency management systemsStrong regulatory and compliance knowledgeBased in San Francisco or willing to relocateNice to HaveInsurance designations (CPCU, CIC, CRM, ARM)Experience building ops infrastructure from scratchPrior startup experienceCompensationSalary: $180,000–$220,000 + performance bonuses & equityLocation: San Francisco, in-officeBenefitsHealth, dental, and vision insuranceCommuter benefitsTeam meals and snacksThe ProcessInitial screen — Skills and culture fit30-min founder call — Alignment on mission and paceOn-site Super Day — Meet the team, work through real scenariosPaid work trial — Real work, real stakes, mutual evaluationTo ApplyIf 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.