Chestnut builds the systems insurance carriers actually run their distribution business on. We replace spreadsheets, legacy vendor systems, and manual processes with real-time data, deterministic workflows, and AI-assisted tooling.
This is end-to-end product engineering.
You won’t just write APIs. You’ll design schemas, build backend logic, ship UI, deploy to production, and handle the sharp edges that show up with real customers. The problems are messy and state-heavy: payouts that must reconcile with finance, onboarding flows with regulatory constraints, dynamic hierarchies, retries, chargebacks, partial failures.
We care a lot about correctness. These systems move real money and cannot drift.
We use AI heavily in our workflow — for drafting, refactoring, test generation, and exploring solutions. We expect engineers to use it aggressively. We also expect you to understand what it’s doing, spot when it’s wrong, and maintain strong fundamentals. Taste matters.
You’ll likely thrive here if you:
- Have 3–6 years building real product systems
- Are strong in at least one typed language and comfortable picking up others
- Enjoy owning features end-to-end
- Think in terms of invariants, edge cases, and failure modes
- Like shipping quickly but cleanly
- Want to build systems that operate in production, not demos
We’re a small, high-agency team. You’ll have meaningful ownership and direct impact on customers.
Hybrid in SF and Seattle.
Questions or want to sanity-check fit: nick [at] chestnutfi [dot] com
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.
Massive opp. Chestnut is the first AI-native operating system for insurance distribution management, tackling a $100B+ spend pool in the largest industry in the U.S. Legacy software and manual processes dominate this space; Chestnut is the only modern platform enabling real-time data, automation, and agentic AI workflows that directly grow carrier revenue.
** Engineer [Agent Orchestration] – Focus on applied systems: multi-agent coordination, workflow automation, retrieval, and tool use. Bridge research to production and design orchestration layers for enterprise reliability. https://jobs.ashbyhq.com/Chestnut/075a0010-bfa5-489e-8808-e9...
** Engineer [ML + Agent Design] – Experiment with prompting, fine-tuning, and novel LLM techniques. Prototype new agent behaviors and push the boundaries of how models reason, interact, and automate in data-heavy domains. https://jobs.ashbyhq.com/Chestnut/0b6e2b45-fab9-47f2-8f10-30...
We’re also hiring for Product & Commercial Lead and Data + Infra roles (details on the site).
******
You'll work on the bleeding edge - embedding enterprise-grade agentic AI at scale. We're looking for engineers who thrive in fast-paced environments and want to make a meaningful impact.
We're a well funded (a16z) close-knit seed stage insurtech - building next-gen enterprise infrastructure for the $7T insurance industry.
If you are a passionate full stack Golang Developer with a track record of building high-quality applications and want to be part of a vibrant team that embraces innovation, we'd love to hear from you!
We're a well funded (a16z) close-knit seed stage insurtech - building next-gen enterprise infrastructure for the $7T insurance industry.
If you are a passionate full stack Golang Developer with a track record of building high-quality applications and want to be part of a vibrant team that embraces innovation, we'd love to hear from you!
Chestnut | Multiple Roles: Sr Software Engineer (3+ YoE), QA Lead | San Francisco, CA (HYBRID) | Full Time | https://jobs.ashbyhq.com/Chestnut
We're a well funded (a16z) close-knit seed stage insurtech - building next-gen enterprise infrastructure for the $7T insurance industry.
If you are a passionate full stack Golang Developer with a track record of building high-quality applications and want to be part of a vibrant team that embraces innovation, we'd love to hear from you!
Chestnut is a well funded (a16z) close-knit seed stage insurtech - building next-gen enterprise infrastructure for the insurance industry. If you are a passionate full stack Golang Developer with a track record of building high-quality applications and want to be part of a vibrant team that embraces innovation, we'd love to hear from you!
Chestnut is a well funded (a16z) close-knit seed stage insurtech - building next-gen enterprise infrastructure for the insurance industry. If you are a passionate full stack Golang Developer with a track record of building high-quality applications and want to be part of a vibrant team that embraces innovation, we'd love to hear from you!
Chestnut is a well funded (a16z) close-knit seed stage insurtech - building next-gen enterprise infrastructure for the insurance industry. If you are a passionate full stack Golang Developer with a track record of building high-quality applications and want to be part of a vibrant team that embraces innovation, we'd love to hear from you!
Chestnut is a well funded (a16z) close-knit seed stage insurtech - building next-gen enterprise infrastructure for the insurance industry. If you are a passionate full stack Golang Developer with a track record of building high-quality applications and want to be part of a vibrant team that embraces innovation, we'd love to hear from you!
Chestnut builds the systems insurance carriers actually run their distribution business on. We replace spreadsheets, legacy vendor systems, and manual processes with real-time data, deterministic workflows, and AI-assisted tooling.
This is end-to-end product engineering.
You won’t just write APIs. You’ll design schemas, build backend logic, ship UI, deploy to production, and handle the sharp edges that show up with real customers. The problems are messy and state-heavy: payouts that must reconcile with finance, onboarding flows with regulatory constraints, dynamic hierarchies, retries, chargebacks, partial failures.
We care a lot about correctness. These systems move real money and cannot drift.
Stack: Go, TypeScript/React, Postgres, Temporal, Kubernetes, AWS
We use AI heavily in our workflow — for drafting, refactoring, test generation, and exploring solutions. We expect engineers to use it aggressively. We also expect you to understand what it’s doing, spot when it’s wrong, and maintain strong fundamentals. Taste matters.
You’ll likely thrive here if you: - Have 3–6 years building real product systems - Are strong in at least one typed language and comfortable picking up others - Enjoy owning features end-to-end - Think in terms of invariants, edge cases, and failure modes - Like shipping quickly but cleanly - Want to build systems that operate in production, not demos
We’re a small, high-agency team. You’ll have meaningful ownership and direct impact on customers.
Hybrid in SF and Seattle.
Questions or want to sanity-check fit: nick [at] chestnutfi [dot] com