Software Engineer (Mid-Level)

About The Company
Chestnut is pioneering the future of insurance distribution by developing the first AI-native operating system specifically designed for the insurance industry. With a focus on transforming how the over $1 trillion insurance sector allocates its largest expenditure—sales and distribution—Chestnut is revolutionizing traditional processes through innovative technology. Backed by prominent investors such as a16z, the company is replacing legacy systems with a modern, flexible platform that enables carriers to automate complex workflows, optimize distribution channels, and unlock new avenues for growth. Chestnut has secured contracts with major insurers and is experiencing rapid expansion as early adopters increase their engagement. The company's mission is rooted in leveraging recent advancements in agentic AI to automate manual and error-prone tasks, thus facilitating a generational shift in insurance operations. Committed to a high-impact, high-efficiency work environment, Chestnut emphasizes small, high-context teams equipped with best-in-class tools to achieve outsized results. The organization values innovation, agility, and a relentless pursuit of productivity gains, aiming to scale impact beyond headcount and traditional industry limitations.
About The Role
As a Software Engineer at Chestnut, you will be integral to building the modern infrastructure that powers AI-driven insurance operations. Your work will involve developing the core components of our AI-native platform, including Go services, event-driven workflows, React-based user interfaces, and automation layers. You will collaborate closely with product managers and designers to deliver impactful features rapidly, embracing a fast-paced, iterative development process. The role offers ownership of projects from architecture through deployment, fostering a culture of accountability and continuous improvement. You will contribute to scaling our foundational infrastructure, focusing on observability, permissions, and developer tooling to support a high-performance environment. The ideal candidate is a proactive builder who can navigate challenges with urgency and prioritize tasks effectively, ensuring the delivery of high-quality solutions that drive the company's mission forward.
Qualifications
3+ years of experience building and scaling production systems
Proficiency in Go, TypeScript, and React
Strong computer science fundamentals with a focus on designing durable systems
Hands-on experience with gRPC, event-driven architecture, and clean, versioned APIs
Fluency in containerization and orchestration tools such as Temporal, Dagster, and ArgoCD
Experience with infrastructure management, including observability, permissions, and developer tooling
Ability to thrive in fast-paced, high-autonomy environments and make strategic tradeoffs
Curiosity about AI technologies and motivation to influence foundational systems in a large industry
Responsibilities
Develop and maintain the core components of our AI-native platform, including backend services, workflows, and user interfaces
Collaborate with cross-functional teams to define, design, and ship high-impact features quickly and efficiently
Take ownership of projects from initial architecture to deployment, ensuring reliability and scalability
Enhance infrastructure capabilities such as observability, permissions management, and developer tooling
Act proactively to unblock development processes, act with urgency, and focus on delivering value
Contribute to technical culture by sharing best practices and fostering continuous learning
Stay informed about emerging AI and software development trends to inform platform evolution
Benefits
Competitive salary and equity package, with a 10-year exercise window for stock options
Remote-first work environment emphasizing trust, autonomy, and high performance
Team offsites to promote 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. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status.

Work arrangement
Yes