Software Engineer (Staff-Level)

About Chestnut

Chestnut is building the 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 platform that allows carriers to automate workflows, optimize distribution spend, and unlock new growth. We have major fortune 500 insurers live and under contract. They’re already expanding.

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 team size.

This is especially true in this builder function, where team members are running data migration scripts and shipping production PRs. We are building an AI-driven deployment engine, bringing down the time-to-value from the industry standard of quarters to that of weeks.

If you’re excited to realize the true impact of AI in one of America’s most essential industries, we’d love to meet you. 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