Job Description
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.
We’re building the inverse: a 90%+ AI-led commercial insurance platform — and defining what the human layer should be.
We’re 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.
You’ll:
- 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 isn’t “How do we respond faster?”
It’s “Why are we responding at all?”
You Might Be a Fit If:
- You’ve scaled CX/Ops through 10x+ growth
- You’ve built systems, not just hired teams
- You’re comfortable in sprint planning, specs, UAT, and prioritization tradeoffs
- You’ve personally handled escalations at scale
- You default to building before buying
Bonus: Experience in insurance, fintech, lending, or other regulated environments.
If you’ve survived hypergrowth and want to design the operating system that powers a computational insurance business, let’s talk.