Head of Customer Operations & Product Partnerships

Harper•San Francisco, CA

4d•$185,000 - $250,000•Onsite

About The Position

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. We’re taking 5,000 customers to 100,000+ this year, and 1M+ from there. This is extreme hypergrowth—and Customer Ops is where it all gets real. You’ve scaled customer operations through hypergrowth. You’ve watched volume spike 10x and “just hire more people” stop working. We’re not a brokerage that uses AI—we’re computational insurance distribution. The AI infrastructure already exists. Your job is to define what the human layer should be, and work hand-in-hand with Product and Engineering to build the systems that let Customer Ops scale non-linearly. This isn’t a call center leadership role. It’s an operator + builder role where the question isn’t “how do we respond faster?”—it’s “why are we responding at all?” You own the full service lifecycle and outcomes: COIs, endorsements, renewals, claims coordination (triage, carrier comms, customer guidance), billing escalations, carrier follow-ups, quality, and escalation management. You’ll work extremely closely with Product and Engineering to shape what gets built—not as “the PM,” but as the operator who surfaces the highest-leverage problems, translates them into clear requirements, helps prioritize what matters, and validates solutions in production with real metrics and real customer feedback. You’ll inherit a small, experienced team with insurance industry veterans. You’re not starting from zero—but you’re building the scalable version. Reports directly to CEO.

Requirements

Proven experience scaling CX/Ops through hypergrowth (10x+ volume)
Track record partnering deeply with Product/Engineering on ops tooling, workflows, or self-serve
Fluency in software development cycles: prioritization tradeoffs, edge cases, testing, iteration
Experience building scalable operating models (tiers, routing, escalation paths, QA/calibration)
Hands-on leadership style—you’ll work real tickets/escalations to learn the operation
Based in San Francisco or willing to relocate immediately

Nice To Haves

Background in regulated, high-stakes industries (insurance, fintech, healthcare)
Ex-founder who owned ops end-to-end
Experience with AI/automation in customer operations
Prior startup or high-growth company experience

Responsibilities

Own end-to-end customer operations — COIs, endorsements, renewals, claims coordination, billing escalations, carrier follow-ups, quality, and trust
Partner deeply with Product + Engineering — Surface problems, translate to requirements, prioritize, validate solutions in production
Drive productization of service — Customer portal, self-serve flows, internal routing/triage tooling, automation guardrails
Build scalable systems — Map workflows into AI → self-serve → human → escalation; instrument everything
Establish the defect loop — Weekly cadence with Product/Eng so recurring issues get fixed upstream
Ship quick wins — Immediately reduce repeat contacts and rework while building the long-term model