About the job
About Chestnut
Chestnut is pioneering the first AI-native operating system tailored for the insurance distribution sector, revolutionizing how the $1 trillion-plus insurance industry allocates its most significant expense: sales and distribution.
Supported by a16z, we are replacing outdated systems with a modern, adaptable platform that empowers carriers to automate intricate workflows, optimize every dollar spent on distribution, and unlock new avenues for growth. We have secured contracts with major insurers, and early adopters are broadening their engagement.
This represents a generational shift in platform technology. Recent breakthroughs in agentic AI allow us to automate processes that were once manual and prone to error. After years of developing the data model and context layer necessary for this transformation, we are now scaling with a sense of urgency.
At Chestnut, we believe that small, high-context teams equipped with top-tier tools and colleagues can achieve remarkable outcomes. We embody an AI-lean approach, pursuing 10x productivity gains that enable us to amplify our impact beyond our current 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 establishing the foundation for intelligent automation, your contributions will drive a once-in-a-generation transformation.
Product & Commercial Lead at Chestnut
As our Product & Commercial Lead, you will play a pivotal role in managing customer relationships and steering the success of Chestnut's deployments from start to finish. You will immerse yourself in our customers' operations, gain a deep understanding of their workflows, and lead the transformation of their distribution processes using Chestnut’s platform.
This position combines product strategy, execution, and customer collaboration. You will identify gaps, prototype solutions, and collaborate closely with deployed engineers and designers to transform customer-specific insights into scalable product outcomes. You’ll oversee project timelines, influence both internal and external stakeholders, and uncover opportunities for core platform development and AI automation. Unlike a traditional Product Manager role, you will drive significant outcomes not only within the core platform but also across commercial operations.
As the architect of our customers' success, you are curious, autonomous, relentless, and ready to act swiftly with incomplete information. You will translate ambiguous feedback into tangible product improvements and help redefine the operational landscape of the insurance industry.

