Head of Customer Experience

The Problem

36 million businesses in America need insurance—it's not optional. 77% are underinsured. 40% have no coverage at all. The distribution system failed them: too slow, too opaque, too confusing.

Over 90% of commercial insurance is still human-led. We're building the inverse: 90%+ AI-led, pushing toward the higher 90s. Not by patching legacy workflows—by building AI that makes humans more effective, improves the customer experience, and eliminates friction at every step.

We're adding ~1,000 customers per month. We've grown 100x since last year. We're looking to do even more this year—and that's why we're hiring.

We're taking 5,000 customers to 100,000+ this year, and 1M+ from there. This is extreme hypergrowth—and Customer Experience is where it all gets real.

The Thesis

You'll open the ticketing system on day one. You'll work real customer issues—COIs, billing disputes, claims questions—to learn the operation from the inside. You've done this before. It's how you've always ramped, and you wouldn't have it any other way.

We're not a brokerage that uses AI—we're computational insurance distribution. We've already built the AI infrastructure: our own operating system, our own AI agent, our own internal tooling. Your job isn't to replace any of that with off-the-shelf software. It's to shape it—to define what the human layer should be and work directly with engineers to build the systems that let CX scale non-linearly.

This isn't a call center leadership role. It's an operator + builder role where the question isn't "how do we respond faster?"—it's "why are we responding at all?"

The Role

You own the full service lifecycle and outcomes: COIs, endorsements, renewals, claims coordination (triage, carrier comms, customer guidance), billing escalations, carrier follow-ups, quality, and escalation management.

You own the product roadmap for CX tooling. You spec it, you prioritize it, you validate it in production with real metrics and real customer feedback. You work directly with engineers as a thought partner—not a requestor who submits tickets and waits. When there's a tooling gap, your instinct is to figure out what you can build with what exists, not to evaluate vendors.

You'll inherit a small, experienced team of insurance industry veterans. You're not starting from zero—but you're building the scalable version. There is no large support structure waiting for you. No dedicated CRM team, no project managers, no integration specialists. You'll operate with what's here and build from it. Reports directly to CEO.

This is a small team, high-intensity, high-ambiguity environment. The CEO is in the weeds daily. Everyone operates well beyond their job description. If that sounds like where you do your best work, keep reading.

What You'll Do

Get in the queue — Work real tickets and escalations from day one to learn the customer, the product, and the operation from the inside out

Ship quick wins — Immediately reduce repeat contacts and rework while building the long-term model

Own end-to-end customer experience — COIs, endorsements, renewals, claims coordination, billing escalations, carrier follow-ups, quality, and trust

Own the CX product roadmap — Spec, build, and validate CX tooling with engineering: customer portal, self-serve flows, routing/triage, automation guardrails. You are the product thinker for this domain.

Build scalable systems — Map workflows into AI → self-serve → human → escalation; instrument everything

Establish the defect loop — Weekly cadence with Product/Eng so recurring issues get fixed upstream, not patched with more headcount

You Might Be a Fit If…

Your first move in a new role is to open the ticketing system and start working real issues

You've been in a CX/Ops role during hypergrowth—you know what breaks at 10x, 50x, 100x

You've been at a company between Series B and IPO and lived through what breaks at each stage

You've built systems that survive extreme scale, not just hired pro