Staff Software Engineer

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, were 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. Weve spent years building the data model and context layer required to make this real, and now were 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 youre excited to modernize the infrastructure of one of Americas most essential industries, wed 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

Were 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, youll join a high-agency, cross-functional team focused on delivering impactful features fast. Youll work across the stack, contribute to system design, and help shape the technical culture as we grow.

What Youll 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