Senior Product Engineer

I'm Nick, CTO & co-founder. We're Rippling, but for insurance carriers paying their sales force. Every policy sold triggers a chain of payouts across brokers, agents, and sub-agents. Today that runs on spreadsheets and legacy vendor systems and tomorrow they'll run on Chestnut. Nationwide and other major carriers have already made the switch.

Revenue is up 8x in the last year. We're backed by a16z. Founding team came out of leadership at Ethos (insuretech that recently IPO'd in January).

The work is state-heavy and correctness-critical: payouts that must reconcile with finance to the cent, dynamic agent hierarchies, retries, chargebacks, partial failures. These systems move real money and cannot drift.

You'll design schemas, build backend logic, ship UI, deploy, and own the sharp edges that show up with real enterprise customers.

Stack: Go, TypeScript/React, Postgres, Temporal, Kubernetes, AWS. We use AI aggressively and expect you to as well.

We're looking for 3–6 years on real product systems. You're thoughtful about invariants and failure modes.

Apply: https://jobs.ashbyhq.com/Chestnut

Email me: nick at chestnutfi.com