About Chestnut

Chestnut is building the first AI-native operating system for insurance distribution by transforming how the $1T+ insurance industry allocates its largest spend: sales and distribution.

Backed by a16z, we’re replacing legacy systems with a modern, flexible platform that helps carriers automate complex workflows, optimize every distribution dollar, and unlock new growth. We have major insurers under contract, and early adopters are expanding.

This is a generational platform shift. Recent advances in agentic AI make it possible to automate what was once manual and error-prone. We’ve spent years building the data model and context layer required to make this real, and now we’re scaling with urgency.

At Chestnut, we operate with the belief that small, high-context teams working with best-in-class tools and colleagues can achieve outsized results. We embody what it means to be AI-lean: chasing 10x productivity gains that allow us to scale impact beyond our headcount.

If you’re excited to modernize the infrastructure of one of America’s most essential industries, we’d love to meet you. Whether shaping core product experiences or laying the groundwork for intelligent automation, your work will accelerate a once-in-a-generation transformation.

Engineering at Chestnut

We’re building the modern infrastructure for AI-driven insurance operations. That means well-structured data models, real-time event pipelines, clean APIs, and usable tools that support humans and agents working in parallel.

As a Software Engineer at Chestnut, you’ll join a high-agency, cross-functional team focused on delivering impactful features fast. You’ll work across the stack, contribute to system design, and help shape the technical culture as we grow.

What You’ll Do

• 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

You Might Be a Fit If You…

• 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

Our Stack

• Languages: Go, TypeScript

• Frontend: React, Tailwind

• Infra: K8s, ArgoCD, Kargo, Temporal, Dagster

• Data: Postgres, Dynamo, Snowflake

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