Head of Customer Experience at Harper

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. 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 inte