Software Engineer 2

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

• Build 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

You Might Be a Fit If You…

• 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

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