---
title: 'Software Engineer (Senior-Level) at Chestnut'
canonical: 'https://feeny.ai/job/software-engineer-senior-level-chestnut-san-francisco-wqsr49yp6fk0'
type: 'job'
last_seen: '2026-09-09'
---

# Software Engineer (Senior-Level) at Chestnut

- **Company:** Chestnut
- **Location:** San Francisco, CA
- **Employment:** full-time
- **Work type:** hybrid
- **Posted:** 2025-07-30
- **Last confirmed live:** 2026-09-09
- **Apply:** https://jobs.ashbyhq.com/chestnut/fbbb7601-3d31-48b4-8639-7530cd1afbd0

## Job description

## ABOUT CHESTNUT

Chestnut is building the first AI-native operating system for insurance distribution by transforming how the $1T+ insurance industry allocates its largest spend: sales and distribution.

Backed by a16z, we’re replacing legacy systems with a modern, flexible platform that helps carriers automate complex workflows, optimize every distribution dollar, and unlock new growth. We have major insurers under contract, and early adopters are expanding.

This is a generational platform shift. Recent advances in agentic AI make it possible to automate what was once manual and error-prone. We’ve spent years building the data model and context layer required to make this real, and now we’re scaling with urgency.

At Chestnut, we operate with the belief that small, high-context teams working with best-in-class tools and colleagues can achieve outsized results. We embody what it means to be AI-lean: chasing 10x productivity gains that allow us to scale impact beyond our headcount.

If you’re excited to modernize the infrastructure of one of America’s most essential industries, we’d love to meet you. Whether shaping core product experiences or laying the groundwork for intelligent automation, your work will accelerate a once-in-a-generation transformation.

## ENGINEERING AT CHESTNUT

We’re building the modern infrastructure for AI-driven insurance operations. That means well-structured data models, real-time event pipelines, clean APIs, and usable tools that support humans and agents working in parallel.

As a Software Engineer at Chestnut, you’ll join a high-agency, cross-functional team focused on delivering impactful features fast. You’ll work across the stack, contribute to system design, and help shape the technical culture as we grow.

## WHAT YOU’LL DO

- Lead the design and development of core systems - from Go microservices and event-driven workflows to React UIs and automation layers
- Partner cross-functionally to scope, prioritize, and deliver high-impact features that drive real business outcomes
- Own architecture and implementation decisions end-to-end, ensuring long-term scalability and reliability
- Contribute to and evolve core infrastructure, including observability, permissions, and developer experience
- Set the bar for technical excellence - mentoring teammates, improving processes, and helping us scale with confidence

## YOU MIGHT BE A FIT IF YOU…

- Have 5+ years of experience building and scaling production systems
- Thrive in early-stage environments and enjoy wearing many hats
- Write clean, maintainable code and care about craftsmanship
- Think in systems and design with an eye toward flexibility and resilience
- Take ownership, act with urgency, and bias toward progress over perfection
- Are energized by real-world complexity, data modeling, and automation
- Want to help define the future of engineering at Chestnut

## Our Stack

- Languages: Go, TypeScript
- Frontend: React, Tailwind
- Infra: K8s, ArgoCD, Kargo, Temporal, Dagster
- Data: Postgres, Dynamo, Snowflake

## BENEFITS

- Competitive salary and equity, with 10 year exercise window for stock options
- Remote-first culture built on trust, autonomy, and high performance
- Team offsites for all of us to bond
- Take what you need vacation policy
- Top notch health, dental, and vision insurance subsidized by us

## About Chestnut

## Company Overview
- **One-liner**: Chestnut builds an AI-native operating system for insurance distribution management, streamlining producer onboarding, incentive compensation, and debt collection for carriers.
- **Entity Type**: Private (Seed stage)
- **Headquarters**: Seattle, Washington, United States
- **Founded**: 2022
- **Founders**: David Zhang (CEO & Co-Founder), Nicholas Hilem (CTO & Co-Founder)

## Core Business
- **Primary industry/industries**: Insurance technology (Insurtech) – distribution management, incentive compensation, producer lifecycle management.
- **Target customers**: B2B – insurance carriers (Life & Annuity, P&C), distribution operations teams.
- **Mission statement**: "To empower insurance carriers and producers with purpose-built technology" – working toward a world where insurance distribution is transparent, data-driven, and fully AI-optimized [chestnutfi.com](https://www.chestnutfi.com/about).

## Products & Services
- **[Producer Management Platform]**: Cloud-native system for managing producer operations – onboarding, hierarchy management, performance insights, compliance tracking, and producer self-service portal. Type: SaaS.
- **[Incentive Compensation Management]**: AI-powered compensation engine purpose-built for insurance, handling earned/unearned commissions, advances, chargebacks, vesting, and real-time calculations. Type: SaaS.
- **[Collections & Debt Management]**: Automated collections workflows, debt tracking, and integration with compensation systems to reduce operational risk. Type: SaaS.

All products are built on an API-first, MCP-ready backend with a purpose-built data model covering 250+ insurance-native data concepts [chestnutfi.com](https://chestnutfi.com/).

## Market Standing
- **Valuation/Market Cap**: Not publicly available (private company).
- **Key Metric**: Total funding – Seed round closed on 2022-03-25 (amount undisclosed, led by Andreessen Horowitz) [linkedin.com](https://www.linkedin.com/company/chestnutfi).
- **Notable Investors/Partners**: Andreessen Horowitz (a16z) – portfolio company [linkedin.com](https://www.linkedin.com/company/chestnutfi).
- **Growth Signals**:
  - Headcount growth of +11.8% YoY (17 employees as of mid-2026) [linkedin.com](https://www.linkedin.com/company/chestnutfi).
  - Went live at a Fortune 100 insurance carrier in early 2026, replacing a legacy system [linkedin.com](https://www.linkedin.com/company/chestnutfi).
  - Finalist in the State Farm Startup Pitch Competition at InsureTech Connect (ITC) Vegas 2025 [linkedin.com](https://www.linkedin.com/company/chestnutfi).
  - Listed as a Solutions Provider on Insurtechlist.com [insurtechlist.com](https://insurtechlist.com/companies/chestnut/).

## Competitive Advantages
- **Purpose-built for insurance**: Unlike generic compensation platforms, Chestnut is designed specifically for insurance distribution’s unique rules (earned/unearned commissions, hierarchies, chargebacks).
- **AI-native OS**: Combines a purpose-built data model with an API-first architecture and agentic AI layer to power automation, insights, and agentic workflows – not just a bolt-on AI feature.
- **Speed and flexibility**: Carriers can adapt hierarchies, integrate external data, and evolve compensation strategies without months of custom work. Implementation times are significantly faster than legacy systems [linkedin.com](https://www.linkedin.com/company/chestnutfi).
- **Modern tech stack**: Cloud-native, API-first, uses Typescript, React, AWS, gRPC, Protobuf – positions them to scale and integrate easily [linkedin.com](https://www.linkedin.com/company/chestnutfi).

## Strategic Focus
- **Current priorities**: Continue expanding enterprise carrier relationships (recent Fortune 100 win), deepen AI capabilities for agentic workflows, and scale the platform to handle more insurance verticals (Life & Annuity, P&C). Goal is to make distribution a strategic growth driver rather than a cost center.
- **Direction**: Replace legacy, siloed, outdated systems with a modern, AI-optimized operating system that serves as the durable system of record for insurance distribution.

## Why Work Here
- **Culture**: Values include "Always Build Trust," "Meritocracy Over Hierarchy," "Focus on Outcomes," and "Today, Not Tomorrow" – emphasis on honest feedback, action, and challenging the status quo [chestnutfi.com](https://www.chestnutfi.com/about).
- **Remote-first**: All roles listed (Senior Frontend Developer, Senior Backend Developer, Senior Fullstack Developer, Industry Consultant) are remote [jobs.ashbyhq.com](https://jobs.ashbyhq.com/chestnut).
- **Engineering team**: 32% of employees are technical, with a lean team of ~17 people – small and scrappy environment where contributions matter directly.
- **Perks**: "Life is too short for bad software" – strong product mindset; the team has talent from Ethos, Salesforce, Stripe, Instabase, and other high-caliber tech companies [linkedin.com](https://www.linkedin.com/company/chestnutfi).
- **Growth**: 11.8% YoY headcount growth and recent enterprise wins suggest upward trajectory and expanding opportunities.

## Sources
1. [chestnutfi.com – Product Pages](https://chestnutfi.com/)
2. [jobs.ashbyhq.com – Chestnut Careers](https://jobs.ashbyhq.com/chestnut)
3. [chestnutfi.com – About Page](https://www.chestnutfi.com/about)
4. [linkedin.com – Company Profile](https://www.linkedin.com/company/chestnutfi)
5. [insurtechlist.com – Chestnut Profile](https://insurtechlist.com/companies/chestnut/)

## Other roles at Chestnut

- [Product & Commercial Lead](https://feeny.ai/job/product-commercial-lead-chestnut-remote-6t5kbkq384br)
- [Software Engineer (Staff-Level)](https://feeny.ai/job/software-engineer-staff-level-chestnut-san-francisco-8tj2a9stmmef) — San Francisco, CA
- [Software Engineer (Mid-Level)](https://feeny.ai/job/software-engineer-mid-level-chestnut-san-francisco-0ekd509m4ah0) — San Francisco, CA