Software Engineer (Mid-Level)

Position Overview

Chestnut is revolutionizing the insurance industry by building the first AI-native operating system for insurance distribution. Backed by a16z and major insurers, the company is replacing legacy systems with a modern, flexible platform that automates complex workflows and optimizes distribution dollars. As a Software Engineer at Chestnut, you will work on modern infrastructure for AI-driven insurance operations—working across the stack, contributing to system design, and helping shape the technical culture as the company scales.

Key Responsibilities

• Join a high-agency, cross-functional team to deliver impactful features fast.
• Work across the entire stack and contribute to system design.
• Help shape and evolve the technical culture as the company grows.

Required Qualifications

• Have 3+ years of experience building and scaling production systems with Go, TypeScript, and React.
• Strong CS fundamentals – design thoughtfully and build systems that last.
• Hands-on experience with gRPC, event-driven architecture, and clean, versioned APIs.
• Fluent in containers and modern orchestration tools like Temporal, Dagster, and ArgoCD.
• Thrive in fast-paced, high-agency environments and know how to navigate tradeoffs.
• Curious about AI, drawn to complexity, and motivated to shape foundational systems in a massive industry.

Benefits & Perks

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