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 proportionally

• When there's a tooling gap, you think about how to solve it with what you have before evaluating vendors

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

• You can be effective alone before you have a team at all

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

Requirements

• Proven experience scaling CX/Ops through hypergrowth (10x+ volume) at a startup or high-growth company—not exclusively large, established organizations

• You have personally worked in the queue: you can describe specific tickets, specific customers, and specific resolutions you handled yourself—not through your team

• Track record owning a product roadmap or building internal tooling with engineering—speccing, prioritizing, iterating, shipping—not just submitting requests

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

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

• Experience with AI/automation as a core operating model in customer operations—not a side project

• Default instinct is to build, not buy. When there's a gap, you solve it with what exists or what you can build before reaching for a vendor.

• Comfortable operating with minimal resources, no established tooling, and no fully built team

• 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 in phone-heavy customer operations—not just digital/chat-native environments

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: Personally handle real customer issues to learn the operation. 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.