Software Engineer (Mid-Level)

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.

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

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