Software Engineer (Mid-Level)

About Chestnut

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 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