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: https://jobs.ashbyhq.com/Chestnut

Email me: nick at chestnutfi.com

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

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

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)

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.

Our stack: Go, TypeScript/React, Postgres, Temporal, K8s, Dagster, LLMs.

******

We’re hiring:

** Forward Deployed Engineer – Work directly with customers to ship AI-powered workflows and integrations. https://jobs.ashbyhq.com/Chestnut/5d4fd1ec-60f3-4669-a2d2-31...

** Senior Software Engineer – Build core services, event-driven systems, and automation layers that scale. https://jobs.ashbyhq.com/Chestnut/fbbb7601-3d31-48b4-8639-75...

** Staff Software Engineer – Lead architecture and technical direction as we scale past enterprise workloads. https://jobs.ashbyhq.com/Chestnut/f28c5ee5-12aa-4e7b-b0ea-f5...

** 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.

More info + apply: 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!

* Senior Software Engineer: https://jobs.ashbyhq.com/Chestnut/5513e01d-36fb-43b7-bb98-00...

If interested, you can apply above or reach out to me directly: nick [at] chestnutfi.com

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!

* Senior Software Engineer: https://jobs.ashbyhq.com/Chestnut/5513e01d-36fb-43b7-bb98-00...

If interested, you can apply above or reach out to me directly: nick [at] chestnutfi.com

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!

* Founding Software Engineer: https://jobs.ashbyhq.com/Chestnut/c6df5678-829e-4c98-9dbb-82...

* QA Lead: https://jobs.ashbyhq.com/Chestnut/c7032fc0-8463-455d-b011-f8...

If interested, you can apply above or reach out to me directly: nick [at] chestnutfi.com

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!

Golang, React, k8s, AWS

https://jobs.ashbyhq.com/Chestnut/c6df5678-829e-4c98-9dbb-82...

If interested, you can apply above or reach out to me directly: nick [at] chestnutfi.com

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!

Golang, React, k8s, AWS

https://jobs.ashbyhq.com/Chestnut/c6df5678-829e-4c98-9dbb-82...

If interested, you can apply above or reach out to me directly: nick [at] chestnutfi.com

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!

Golang, React, k8s, AWS

https://jobs.ashbyhq.com/Chestnut/c6df5678-829e-4c98-9dbb-82...

If interested, you can apply above or reach out to me directly: nick [at] chestnutfi.com

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!

Golang, React, k8s, AWS

https://jobs.ashbyhq.com/Chestnut/c6df5678-829e-4c98-9dbb-82...

If interested, you can apply above or reach out to me directly: nick [at] chestnutfi.com

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!

Golang, React, k8s, AWS

https://jobs.ashbyhq.com/Chestnut/c6df5678-829e-4c98-9dbb-82...

If interested, you can apply above or reach out to me directly: nick [at] chestnutfi.com

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!

Golang, React, k8s, AWS

https://jobs.ashbyhq.com/Chestnut/c6df5678-829e-4c98-9dbb-82...

If interested, you can apply above or reach out to me directly: nick [at] chestnutfi.com

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!

Golang, React, k8s, AWS

https://jobs.ashbyhq.com/Chestnut/c6df5678-829e-4c98-9dbb-82...

If interested, you can apply above or reach out to me directly: nick [at] chestnutfi.com

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!

Golang, React, k8s, AWS

https://jobs.ashbyhq.com/Chestnut/c6df5678-829e-4c98-9dbb-82...

If interested, you can apply directly or reach out to me if you have any questions: nick [at] chestnutfi.com

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!

Golang, React, k8s, AWS

https://jobs.ashbyhq.com/Chestnut/c6df5678-829e-4c98-9dbb-82...

If interested, you can apply directly or reach out to me if you have any questions: nick [at] chestnutfi.com

Comments URL: https://news.ycombinator.com/item?id=30835013

Points: 2

# Comments: 0

We're a close-knit team made up of repeat founders with deep industry experience. We just closed a large seed round and are looking to bring on our first hires.

Hiring across the stack:

  - Full Stack Engineer
  - Frontend Engineer (live and breathe UI/UX)
  - Backend Engineer

If interested, you can email me directly: nick [at] getpremium.co