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.
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.
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.
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 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
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
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
Salary: $135,000–$185,000 + performance bonuses & equity
Location: San Francisco, in-office
Health, dental, and vision insurance
Commuter benefits
Team meals and snacks
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
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.