Software Engineer Senior

Summary

Join Chestnut, a company building an AI-native operating system for insurance distribution, and be part of a team transforming the $1T+ insurance industry. As a Software Engineer, you will lead the design and development of core systems, partner cross-functionally to deliver impactful features, and own architecture and implementation decisions. You will contribute to core infrastructure and set the bar for technical excellence by mentoring teammates and improving processes. Chestnut offers a remote-first culture, competitive salary and equity, and excellent benefits. This is a chance to modernize the infrastructure of a crucial industry and help define the future of engineering at Chestnut. The company is backed by a16z and has major insurers under contract.

Requirements

• Have 5+ years of experience building and scaling production systems
• Thrive in early-stage environments and enjoy wearing many hats
• Write clean, maintainable code and care about craftsmanship
• Think in systems and design with an eye toward flexibility and resilience
• Take ownership, act with urgency, and bias toward progress over perfection
• Are energized by real-world complexity, data modeling, and automation
• Want to help define the future of engineering at Chestnut

Responsibilities

• Lead the design and development of core systems - from Go microservices and event-driven workflows to React UIs and automation layers
• Partner cross-functionally to scope, prioritize, and deliver high-impact features that drive real business outcomes
• Own architecture and implementation decisions end-to-end, ensuring long-term scalability and reliability
• Contribute to and evolve core infrastructure, including observability , permissions , and developer experience
• Set the bar for technical excellence - mentoring teammates, improving processes, and helping us scale with confidence

Benefits

• Competitive salary and equity, with 10 year exercise window for stock options
• Remote-first culture built on trust, autonomy, and high performance
• Team offsites for all of us to bond
• Take what you need vacation policy
• Top notch health, dental, and vision insurance subsidized by us