Chestnut

Chestnut builds systems for insurance carriers to run their distribution businesses, replacing spreadsheets and legacy systems with real-time data, deterministic workflows, and AI-assisted tooling. This role is end-to-end product engineering: design schemas, build backend logic, ship UI, deploy to production, and handle edge cases with real customers. Problems include state-heavy workflows like payouts, reconciliation with finance, onboarding with regulatory constraints, dynamic hierarchies, retries, chargebacks, and partial failures. The team emphasizes correctness, ownership, and production-grade systems. Hybrid role in San Francisco and Seattle on a small, high-agency team.