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).
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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 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 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)
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