About the job
About Chestnut
Chestnut is pioneering the first AI-native operating system designed specifically for insurance distribution, revolutionizing how the $1T+ insurance industry manages its most significant expenditures: sales and distribution.
Supported by a16z, we are replacing outdated systems with a cutting-edge, adaptable platform that empowers carriers to automate intricate workflows, maximize every distribution dollar, and unlock new avenues for growth. Our partnerships with major insurers are already in place, and early adopters are witnessing substantial expansion.
We are on the brink of a generational shift in platforms. Recent advancements in agentic AI enable us to automate processes that were once manual and fraught with errors. After years of developing the necessary data model and context layer, we are now scaling with urgency.
At Chestnut, we believe that small, high-context teams, equipped with industry-leading tools and talented colleagues, can deliver exceptional results. We embody the concept of being AI-lean: striving for 10x productivity gains that allow us to amplify our impact beyond our headcount.
If you are passionate about modernizing the infrastructure of one of America’s most vital industries, we would love to connect with you. Whether you are enhancing core product experiences or laying the foundation for intelligent automation, your contributions will accelerate a transformative journey that occurs once in a generation.
Engineering at Chestnut
We are constructing the modern infrastructure necessary for AI-driven insurance operations. This entails well-organized data models, real-time event pipelines, robust APIs, and user-friendly tools that facilitate collaboration between humans and agents.
As a Senior Software Engineer at Chestnut, you will be part of a high-agency, cross-functional team dedicated to delivering impactful features rapidly. You will work across the entire tech stack, contribute to system design, and help shape the technical culture as we expand.

