Job Details

Director of Customer Experience Strategy

San Francisco (On-site)

$185K-$250K + Bonus + Equity

In the United States, 36 million businesses require insurance, yet 77% remain underinsured. The traditional insurance system is often slow, opaque, and relies heavily on humanintervention.

We are transforming this landscape with an AI-driven commercial insurance platform designed to support over 100,000 customers. The Customer Experience (CX) department is crucial to ensuring that our scale enhances rather than complicates our service.

The Opportunity

This role goes beyond typical call center leadership.

You will take charge of the entire service lifecycle—handling Certificates of Insurance (COIs), endorsements, renewals, claims coordination, billing escalations, maintaining quality, and building trust—and you will develop systems that enable CX to grow tenfold without a proportional increase in personnel.

Your responsibilities will include:

• Collaborating directly with the CEO
• Starting at the ground level to understand edge cases
• Working closely with Product and Engineering teams
• Transforming recurring friction points into automated solutions, self-service options, and optimized routing
• Creating a model for AI-driven self-service and human escalation

Instead of asking, 'How can we respond faster?' you will focus on 'Why do we need to respond at all?'

You Could Be the Perfect Candidate If:

• You have successfully scaled CX/Operations during significant growth phases
• You are experienced in building systems rather than just adding team members
• You are adept with sprint planning, specifications, user acceptance testing, and making prioritization trade-offs
• You have navigated large-scale escalations personally
• Your approach favors building solutions over purchasing them

Bonus Points: Experience in insurance, fintech, lending, or other regulated industries.

If you're ready to thrive in a hypergrowth environment and want to help design the foundational system for a computational insurance business, we would love to connect!