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. You’ll be Harper’s first Product Manager, building the connective tissue between engineering and the business. The Thesis We need a technical PM who really understands what we’re building—how AI agents work, how context engineering shapes outcomes, how our systems make decisions. You’ll be the translator between engineering and business, and the gelling function that keeps sales, service, and engineering building toward the same outcomes. This is a rare path to Head of Product. The Role Founding role. You’ll bring owner-style ownership of the end-to-end product lifecycle—the right mix of product management, product marketing, and strategic vision. You work directly with founders to set strategy, manage technical development, and own success from concept to launch. You won’t own a single product—you’ll own a product area. Deeply live and breathe a customer persona. Drive a business outcome. What You’ll Do • Use AI to prototype fast — Spin up prototypes with Claude Code, Cursor, Lovable; show, not tell • Bridge engineering and business — Understand data systems deeply enough to explain what’s possible • Be the gelling function — Break down walls between teams; create shared context • Own a product area end-to-end — Strategy, roadmap, execution, outcomes • Drive business outcomes — North star is revenue and customers, not features shipped • Talk to customers every day — Literally You Might Be a Fit If… • You prototype with AI tools (Claude Code, Cursor, Lovable)—you build before the meeting • You’re a natural translator between technical architecture and business outcomes • You understand data systems deeply (pipelines, AI/ML, APIs, integrations) • You’re a connector who fixes when teams talk past each other • You’ve shipped B2B products from 0→1 and you’re customer-obsessed • You’re not a project manager—you decide, you have strong opinions, you execute Requirements • 3-6 years in product management (B2B SaaS or AI-native preferred) • Technical depth in AI agent architecture, context engineering, LLM-based systems • Proficiency using AI tools to rapidly prototype • Success owning a product from concept through launch • Track record bridging engineering and business teams • Based in San Francisco or willing to relocate Nice to Have • Insurance, fintech, or regulated industry experience • Background in AI/ML products, voice AI, or workflow automation • Prior startup experience (Series A/B) • Experience building product functions from scratch Compensation • Salary: $135,000–$185,000 + performance bonuses & equity • Location: San Francisco, in-office Benefits • Health, dental, and vision insurance • Commuter benefits • Team meals and snacks The Process • Founder screen — Initial fit and alignment • Product case study — Show us how you’d approach a real problem (~1 day turnaround) • On-site day — Meet the team, walk through your case study, see the product To Apply If you’ve built products from zero and can bridge engineering and business like a native speaker of both—send your resume and tell us about a time you connected teams that weren’t connecting.