Staff Software Engineer – Architecture & Scale

Chestnut | Hiring Senior / Staff Software Engineers | SF + Seattle (Hybrid) | https://jobs.ashbyhq.com/Chestnut Chestnut builds software insurance carriers actually run their business on. We replace legacy, manual distribution systems with real-time data, automated workflows, and AI-driven tooling in a space that hasn’t changed much in decades. This is product engineering. We ship to real customers, operate what we build, and spend time fixing the sharp edges that show up in production. You’d work on backend-heavy product features around onboarding, compliance, payouts, and integrations. A representative problem: building a commission payout flow that ingests messy carrier data, applies complex rules and hierarchies, explains results to ops, and executes payouts that must reconcile cleanly with finance—while handling holds, chargebacks, retries, and partial failures. Stack: Go, TypeScript/React, Postgres, Temporal, Kubernetes, AWS, LLM tooling. Roles: - Senior Software Engineer – Product / Backend (https://jobs.ashbyhq.com/Chestnut/fbbb7601-3d31-48b4-8639-75...) - Staff Software Engineer – Architecture & Scale (https://jobs.ashbyhq.com/Chestnut/f28c5ee5-12aa-4e7b-b0ea-f5...) - Engineer – Agent Orchestration & Workflow Systems (https://jobs.ashbyhq.com/Chestnut/075a0010-bfa5-489e-8808-e9...) Hybrid in SF and Seattle. Questions or want to sanity-check fit: nick [at] chestnutfi [dot] com (apologies there was a typo here if you looked earlier)