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

• 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

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