Chestnut is building the 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 platform that allows carriers to automate workflows, optimize distribution spend, and unlock new growth. We have major fortune 500 insurers live and under contract. They’re already expanding.
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 team size.
This is especially true in this builder function, where team members are running data migration scripts and shipping production PRs. We are building an AI-driven deployment engine, bringing down the time-to-value from the industry standard of quarters to that of weeks.
If you’re excited to realize the true impact of AI in one of America’s most essential industries, we’d love to meet you. Your work will accelerate a once-in-a-generation transformation.
Engineering at ChestnutWe’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 DoBuild the backbone of our AI-native platform — from Go services and event-driven workflows to React UIs and automation layers
Work closely with product and design to ship fast, learn quickly, and iterate on high-impact features
Own your work end-to-end — from architecture to deployment, with clear handoffs and strong accountability
Scale our foundation — shaping infrastructure like observability, permissions, and dev tooling
Move like a builder: stay unblocked, act with urgency, and focus on what matters most
Have 3+ years building and scaling production systems with Go, TypeScript, and React
Strong CS fundamentals - you design thoughtfully and build systems that last
Have hands-on experience with gRPC, event-driven architecture, and clean, versioned APIs
Are fluent in containers and modern orchestration tools like Temporal, Dagster, and ArgoCD
Thrive in fast-paced, high-agency environments and know how to navigate tradeoffs
Are curious about AI, drawn to complexity, and motivated to shape foundational systems in a massive industry
Our Stack
Languages: Go, TypeScript
Frontend: React, Tailwind
Infra: K8s, ArgoCD, Kargo, Temporal, Dagster
Data: Postgres, Dynamo, Snowflake
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
Skills Required
- 3-5+ years building and scaling production systems
- Strong CS fundamentals
- Hands-on experience with gRPC, event-driven architecture, clean APIs
- Fluency in containers and modern orchestration tools
- Curiosity about AI and motivation to shape foundational systems
What We Do
Chestnut is on a mission to overhaul the insurance industry's technology and data infrastructure. Our first product is a customizable, easy-to-use, and centralized producer management and compensation system that is purpose-built for the insurance industry. By using our cloud native platform, carriers and their distribution partners can free themselves from operational constraints imposed by legacy software, static compensation structures, and manual processes. We unlock growth opportunities by giving our customers the flexibility and insights needed to manage commissions as a revenue driver instead of as a cost-center and by enabling our customers to better engage with and retain their agents through our mobile-first agent app. We have raised a seed round from notable investors including Andreessen Horowitz, Liquid 2 Ventures, and Detroit Venture Partners to achieve our mission.
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