Job Details

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.