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’ve scaled customer experience through hypergrowth. You’ve watched volume spike 10x and “just hire more people” stop working.

We’re not a brokerage that uses AI—we’re computational insurance distribution. The AI infrastructure already exists. Your job is to define what the human layer should be, and work hand-in-hand with Product and Engineering 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’ll work extremely closely with Product and Engineering to shape what gets built—not as “the PM,” but as the operator who surfaces the highest-leverage problems, translates them into clear requirements, helps prioritize what matters, and validates solutions in production with real metrics and real customer feedback.

You’ll inherit a small, experienced team with insurance industry veterans. You’re not starting from zero—but you’re building the scalable version. Reports directly to CEO.

What You’ll Do

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

• Partner deeply with Product + Engineering — Surface problems, translate to requirements, prioritize, validate solutions in production

• Drive productization of service — Customer portal, self-serve flows, internal routing/triage tooling, automation guardrails

• 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

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

You Might Be a Fit If…

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

• You’ve built systems that survive extreme scale, not just hired proportionally

• You’re comfortable in a real software development cadence: specs, sprint planning, UAT, iteration

• You’ll personally handle escalations—and you want to

• You don’t need a fully-built team before you can be effective

• You see ops problems as product problems waiting to be solved

Requirements

• Proven experience scaling CX/Ops through hypergrowth (10x+ volume)

• Track record partnering deeply with Product/Engineering on ops tooling, workflows, or self-serve

• Fluency in software development cycles: prioritization tradeoffs, edge cases, testing, iteration

• Experience building scalable operating models (tiers, routing, escalation paths, QA/calibration)

• Hands-on leadership style—you’ll work real tickets/escalations to learn the operation

• Based in San Francisco or willing to relocate immediately

Nice to Have

• Background in regulated, high-stakes industries (insurance, fintech, healthcare)

• Ex-founder who owned ops end-to-end

• Experience with AI/automation in customer operations

• Prior startup or high-growth company experience

Compensation

• Salary: $185,000–$250,000 + performance bonuses & equity

• Location: San Francisco, in-office

Benefits

• Health, dental, and vision insurance

• Commuter benefits

• Team meals and snacks

The Process

1. Founder screen — Initial fit and alignment

2. Lead screen — Skills and culture fit

3. Super day — See how you operate in real time

To Apply

What success looks like:

First 60 days: Get hands-on with real tickets. Map workflows into a durable model. Establish baseline instrumentation (contact rate, cycle time, escalation rate, quality, sentiment). Build a Customer Ops roadmap connected to Product/Eng priorities. Ship quick wins.

Within 6 months: A scalable operating model that handles 10x+ volume without 10x headcount. Clear tiers, routing, escalation paths, QA, and training systems. “We get better as we get bigger” is true in practice.

If you’ve survived hypergrowth and built systems that scale non-linearly—send your resume and a few sentences on why this role fits.