Software Engineer (Mid-Level)

About The Company
Chestnut is pioneering the development of the first AI-native operating system tailored for insurance distribution, revolutionizing how the over $1 trillion insurance industry allocates its largest expenditure—sales and distribution. Backed by prominent investors such as a16z, Chestnut is committed to replacing outdated legacy systems with a modern, adaptable platform that empowers insurance carriers to automate complex workflows, optimize distribution channels, and unlock new avenues for growth. The company's innovative approach leverages recent advances in agentic AI, enabling automation of processes that were traditionally manual and error-prone. With a focus on building a generational platform, Chestnut has already secured contracts with major insurers and is experiencing rapid expansion among early adopters. The organization values small, high-context teams working with best-in-class tools to achieve extraordinary results, embodying an AI-lean philosophy aimed at delivering tenfold productivity gains. If you are passionate about transforming a vital industry through cutting-edge technology, Chestnut offers an exciting environment to contribute meaningfully to a once-in-a-generation industry transformation.
About The Role
As a Software Engineer at Chestnut, you will play a crucial role in building the foundational infrastructure for an AI-native insurance platform. Your work will span across the full technology stack, contributing to system design, development, and deployment of impactful features that drive the company's mission forward. You will be part of a high-agency, cross-functional team dedicated to delivering fast, scalable, and reliable solutions. Your responsibilities will include developing core services, working on event-driven workflows, and creating intuitive user interfaces. You will collaborate closely with product and design teams to iterate quickly and ship high-impact features, ensuring the platform remains robust, scalable, and aligned with business goals. Ownership of your work from architecture to deployment will be expected, fostering a culture of accountability and continuous improvement. As the company scales, you will also help shape infrastructure aspects such as observability, permissions, and developer tooling, enabling the team to operate efficiently and effectively in a fast-paced environment.
Qualifications
Minimum of 3+ years of experience building and scaling production systems
Proficiency in Go, TypeScript, and React
Strong understanding of computer science fundamentals
Hands-on experience with gRPC, event-driven architecture, and clean, versioned APIs
Familiarity with containerization and orchestration tools such as Temporal, Dagster, and ArgoCD
Experience working with modern infrastructure and deployment pipelines
Ability to thrive in fast-paced, high-autonomy environments
Curiosity about AI technologies and a desire to shape foundational industry systems
Responsibilities
Develop and maintain the core components of the AI-native platform, including Go services, event-driven workflows, and user interfaces
Collaborate with product and design teams to deliver high-impact features rapidly and iteratively
Take ownership of projects from architecture through deployment, ensuring high quality and reliability
Enhance and scale infrastructure components such as observability, permissions, and developer tooling
Stay unblocked, act with urgency, and prioritize tasks that align with company goals
Contribute to technical discussions and help shape the engineering culture as the team grows
Implement best practices for API design, system security, and performance optimization
Benefits
Competitive salary and equity, with a 10-year exercise window for stock options
Remote-first culture emphasizing trust, autonomy, and high performance
Team offsites to foster bonding and collaboration
Flexible vacation policy allowing you to take what you need
Comprehensive health, dental, and vision insurance subsidized by the company
Equal Opportunity
Chestnut is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We do not discriminate based on race, ethnicity, gender, sexual orientation, age, disability, or any other protected status. We believe that diverse perspectives and backgrounds drive innovation and are essential to our success.

Work arrangement
Yes