Staff Software Engineer

At the heart of Chestnut's mission is a profound belief in the power of small, high-context teams to achieve outsized results. The company operates on the principle that a dedicated and knowledgeable group can revolutionize even the most entrenched industries. This philosophy drives their approach to building the first AI-native operating system specifically for insurance distribution. Chestnut was born from the recognition that the insurance sector, a cornerstone of the American economy, was encumbered by legacy systems. These outdated platforms are often manual, error-prone, and inefficient, creating significant friction for carriers. The team at Chestnut is committed to replacing this antiquated infrastructure with a modern, flexible, and automated platform designed to transform complex workflows.

Chestnut's culture is one of curiosity, pragmatism, and a deep-seated excitement for tackling complex domains like insurance and agentic AI. With a leadership team that brings over 70 years of combined experience from industry giants like Ethos, CallidusCloud/SAP, and Americo Financial, the company is uniquely positioned to understand and address the nuanced challenges faced by insurance carriers. They are not just building software; they are architecting a generational platform shift. By leveraging recent advances in AI, Chestnut aims to automate processes that were once painstakingly manual, thereby turning producer management and incentive compensation from operational burdens into strategic drivers of revenue. For those energized by the prospect of modernizing the foundational infrastructure of a vital industry, Chestnut offers a collaborative and innovative environment to make a significant impact.