Software Engineer

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 implementation of critical systems, make architectural decisions, partner with other leaders to define roadmaps, identify and unblock high-risk areas, and raise the bar for engineering excellence. You will work across the stack, contribute to system design, and help shape the technical culture. This is a high-agency, cross-functional team focused on delivering impactful features quickly. Chestnut offers a remote-first culture, competitive salary and equity, team offsites, flexible vacation, and top-notch health benefits.

Requirements

• Have 8+ years of experience building and scaling complex software systems
• Have led architecture or technical strategy for a product or platform team
• Are comfortable working across backend, data, and infra layers (and diving into frontend when needed)
• Think in systems and excel at finding pragmatic solutions to messy problems
• Are excited to shape the technical direction of a growing company
• Have strong communication skills and enjoy working across disciplines
• Are energized by ambiguity, real-world data, and building for scale

Responsibilities

• Lead the design and implementation of critical systems that serve as building blocks for the platform
• Make architectural decisions that optimize for scale, performance, and maintainability
• Partner with product, design, and other engineering leaders to define roadmaps and scope technical investments
• Identify and unblock high-risk areas across teams, diving deep when needed
• Raise the bar for engineering excellence through mentorship, modeling, and thoughtful code review
• Help establish engineering culture, norms, and hiring standards as we grow

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