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.

What You'll Do

• Design and build the orchestration layer that coordinates multiple AI agents to reliably perform complex enterprise workflows.

• Develop systems that manage agent-to-agent communication, task delegation, retrieval, and tool usage at scale.

• Translate cutting-edge AI techniques into production-ready capabilities.

• Ensure high reliability and fault tolerance in multi-agent systems for mission-critical insurance and compliance operations.

• Continuously improve workflow automation by identifying bottlenecks and engineering scalable solutions.

You Might Be a Fit If You…

• 3+ years of engineering experience in growth-stage startups

• Have experience designing distributed systems or multi-service architectures.

• Enjoy building systems that coordinate multiple intelligent components to achieve end-to-end goals.

• Have strong backend engineering skills and an interest in applied AI systems.

• Understand the challenges of reliability, consistency, and orchestration in enterprise-grade applications.

• Thrive at the intersection of research and production engineering, translating novel AI techniques into practical tools.

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