Head of Insurance Product

36 million businesses in America need insurance—it's not optional. 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: 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. Search before Google. Across them we run a stack of internal AI systems covering operator guidance, the operational backbone that matches risks to underwriters, autonomous communications, and voice AI for customer interactions.

You'll own a module inside this factory end-to-end: the customer experience, the operator workflows, the AI agents underneath. How a daycare buys insurance vs how a trucking company buys it. We're hiring early-career PMs on purpose. You translate what makes your module's customers different into rules, prompts, agents, and data structures.

Regressions on every change, evals that map to real outcomes (not vibes), backtests against historical applications, call-by-call review where it matters. Build the data flywheel — Work hand-in-glove with data labeling and validation to build the golden datasets your module's models need. Own the cross-modal experience — Your module spans web, voice, and human. Talk to customers every day — Literally. We're not selling software. You're shipping behavior into a probabilistic system that real operators and real customers have to trust.

You'd rather ship a worse model with a great eval harness than the other way around.

You think in KPIs—not "we shipped the feature" but "we cut handle time 40%." If you can't tie what you build to a number, you don't ship it.

You can talk shop on AI—agents, LLMs, context engineering, data pipelines, evals. 1-3 years into product, OR an early-career operator, engineer, or AI researcher who's been doing the work without the title

Based in San Francisco or willing to relocate

Salary: $125,000-$170,000 + performance bonuses & equity

Location: San Francisco, in-office

Schedule: Monday-Friday, 5 AM - 8 PM. Health, dental, and vision insurance

On-site — Meet the team, see the data, show us what you’ve got

Commercial insurance has never been rebuilt. The gap between what frontier models make possible and what's actually shipped in this industry is the largest it will ever be.

If you want to own a module that touches real customers from week one, work alongside founders and engineers who ship every day, and learn how to build, measure, and trust AI systems at production scale—send your resume and tell us about something you built that moved a number.