Head of Customer Experience

The Problem36 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 ThesisYou'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 RoleYou 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 DoGet in the queue - Work real tickets and escalations from day one to learn the customer, the product, and the operation from the inside outShip quick wins - Immediately reduce repeat contacts and rework while building the long-term modelOwn end-to-end customer experience - COIs, endorsements, renewals, claims coordination, billing escalations, carrier follow-ups, quality, and trustOwn 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 everythingEstablish the defect loop - Weekly cadence with Product/Eng so recurring issues get fixed upstream, not patched with more headcountYou Might Be a Fit If...Your first move in a new role is to open the ticketing system and start working real issuesYou've been in a CX/Ops role during hypergrowth-you know what breaks at 10x, 50x, 100xYou've been at a company between Series B and IPO and lived through what breaks at each stageYou've built systems that survive extreme scale, not just hired proportionallyWhen there's a tooling gap, you think about how to solve it with what you have before evaluating vendorsYou're comfortable in a real software development cadence: specs, sprint planning, UAT, iterationYou can be effective alone before you have a team at allYou see ops problems as product problems waiting to be solvedRequirementsProven experience scaling CX/Ops through hypergrowth (10x+ volume) at a startup or high-growth company-not exclusively large, established organizationsYou have personally worked in the queue: you can describe specific tickets, specific customers, and specific resolutions you handled yourself-not through your teamTrack record owning a product roadmap or building internal tooling with engineering-speccing, prioritizing, iterating, shipping-not just submitting requestsFluency in software development cycles: prioritization tradeoffs, edge cases, testing, iterationExperience 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 projectDefault 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 teamBased in San Francisco or willing to relocate immediatelyNice to HaveBackground in regulated, high-stakes industries (insurance, fintech, healthcare)Ex-founder who owned ops end-to-endExperience in phone-heavy customer operations-not just digital/chat-native environmentsCompensationSalary: $185,000-$250,000 + performance bonuses & equityLocation: San Francisco, in-officeSchedule: Monday-Friday, 5 AM - 8 PM. The hours are long. The learning curve is steep. The people who thrive here wouldn't have it any other way.BenefitsHealth, dental, and vision insuranceCommuter benefitsTeam meals and snacksThe ProcessFounder screen - Initial fit and alignmentLead screen - Skills and culture fitSuper day - See how you operate in real timeTo ApplyWhat 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.