Head of Customer Experience

Head of Customer Experience ???? San Francisco (On-site) ???? $185K$250K + Bonus + Equity 36 million businesses in America need insurance. 77% are underinsured. The system is slow, opaque, and human-heavy. Were building the inverse: a 90%+ AI-led commercial insurance platform and defining what the human layer should be. Were scaling from 5,000 ? 100,000+ customers. Customer Experience is where that scale either breaks or compounds. The Role This is not a call center leadership role. You will own the full service lifecycle COIs, endorsements, renewals, claims coordination, billing escalations, quality, and trust and build the systems that allow CX to scale 10x without 10x headcount. Youll: Work directly with the CEO Start in the queue to learn the edge cases Partner deeply with Product & Engineering Turn recurring friction into automation, self-serve, and smarter routing Build the AI ? self-serve ? human ? escalation model The question isnt How do we respond faster? Its Why are we responding at all? You Might Be a Fit If: Youve scaled CX/Ops through 10x+ growth Youve built systems, not just hired teams Youre comfortable in sprint planning, specs, UAT, and prioritization tradeoffs Youve personally handled escalations at scale You default to building before buying Bonus: Experience in insurance, fintech, lending, or other regulated environments. If youve survived hypergrowth and want to design the operating system that powers a computational insurance business, lets talk.

Created: 2026-03-06