Job Details

Director of Customer Experience

San Francisco (On-site)

$185K-$250K + Bonus + Equity

With 36 million businesses in America needing insurance and 77% being underinsured, the traditional systems are often slow, opaque, and heavily reliant on human intervention.

We are creating a transformative solution: a 90%+ AI-led commercial insurance platform that reimagines the role of human interaction in insurance.

As we scale from 5,000 to over 100,000 customers, the Customer Experience (CX) will be crucial to our success, determining whether our growth is sustainable or chaotic.

The Role

This is not a typical call center leadership position.

You will take full ownership of the service lifecycle—including COIs, endorsements, renewals, claims coordination, billing escalations, quality assurance, and customer trust—and create systems to enable CX to scale efficiently without exponentially increasing headcount.

In this role, you will:

• Collaborate closely with the CEO
• Begin by working within the queue to understand edge cases
• Engage in deep partnerships with Product & Engineering teams
• Transform recurring frustrations into automated solutions, self-service options, and enhanced routing
• Develop an AI-driven self-service model for human escalation

We are asking not just how to respond more quickly, but why we need to respond at all.

You may be the ideal candidate if you:

• Have successfully scaled CX/Ops through significant growth (10x or more)
• Have a proven track record of building effective systems rather than just expanding teams
• Are comfortable navigating sprint planning, specifications, user acceptance testing, and prioritization trade-offs
• Have experience managing escalations at scale
• Prefer building in-house solutions over purchasing third-party products

Bonus points if you have experience in insurance, fintech, lending, or other regulated environments.

If you have thrived in a hypergrowth setting and are ready to design the operational framework for a cutting-edge computational insurance business, we would love to hear from you.