About

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.

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.

We’re hiring a junior Forward Deployed Engineer to help us bring our product to life inside customer environments. You’ll work on real problems, in production, with real users—often within weeks of joining. If you’re the kind of engineer who wants to understand the business, talk to customers, and ship scrappy-but-scalable solutions, this role gives you the playground and the pressure.

• Implement our platform for new customers—mapping data, building workflows, writing glue code

• Write scripts, API calls, and internal tools to unblock onboarding and drive adoption

• Support onboarding efforts by translating messy customer data into structured, usable formats

• Work alongside senior engineers and solutions folks to turn customer needs into delivered outcomes

• Identify gaps in current tooling and suggest improvements to our AI and deployment stack

• Learn a ton. This is a high-context, high-velocity role, and we’ll invest in helping you grow

• 0–2 years experience, with solid coding fundamentals (Python, Go, or TypeScript ideal)

• Curious, resourceful, and biased toward action—you’re not afraid to figure things out

• Interest in applied AI—whether it’s workflow automation, data enrichment, or retrieval-augmented generation

• Strong communicator who wants to understand both the tech and the business

• Comfortable with ambiguity, eager to learn from others, and motivated to own real problems

• Willingness to travel up to 25% for high-leverage, in-person work

• Bonus: experience with LLMs, open-source AI tools, or side projects that shipped

You want to do more than just write code—you want to build things people actually use. You’re excited about AI, but you care more about what it can do than how it’s marketed. You want to be close to the customer, close to the product, and in the room as decisions get made. We’ll give you real scope, real mentorship, and a real path to grow.

• Languages: Go, TypeScript

• Frontend: React

• Orchestration: Temporal, Dagster

• Infra: AWS, K8s, ArgoCD

• Data: Postgres, Dynamo, Snowflake

• 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