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Roles
Tech stack
Required
Location
SF or Seattle (Hybrid)
Work setup
- Employment
- Full-time
- Level
- Senior
- Remote policy
- Hybrid (SF or Seattle)
- Remote scope
- unclear
- Authorization
- unclear
Role details
Responsibilities
- Design schemas
- Build backend logic
- Ship UI
- Deploy
- Own the sharp edges that show up with real enterprise customers
- Handle correctness-critical payout flows including reconciliation and failure scenarios
Requirements
- 3–6 years on real product systems
- Thoughtful about invariants and failure modes
- State-heavy, correctness-critical work with dynamic agent hierarchies, retries, chargebacks, and partial failures
Application
Apply via https://jobs.ashbyhq.com/Chestnut
- Portfolio
- not required
- GitHub
- not required
- Cover letter
- not required
- Apply flow
- ats
- Canonical URL
- https://jobs.ashbyhq.com/Chestnut
Company context
Power insurance carriers’ payout chains from spreadsheets and legacy vendor systems to modern systems
- Product
- Software platform for insurance carriers handling sales force payouts and policy-triggered payout chains
- Industry
- Insurance
- Stage
- startup
- Funding
- Backed by a16z
Contact
Nick
nick@chestnutfi.com
Description
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 via https://jobs.ashbyhq.com/Chestnut. Email: nick at chestnutfi.com.
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