ChestnutChestnut 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 ChestnutWe'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 DoLead the design and development of core systems - from Go microservices and event-driven workflows to React UIs and automation layersPartner cross-functionally to scope, prioritize, and deliver high-impact features that drive real business outcomesOwn architecture and implementation decisions end-to-end, ensuring long-term scalability and reliabilityContribute to and evolve core infrastructure, including observability, permissions, and developer experienceSet the bar for technical excellence - mentoring teammates, improving processes, and helping us scale with confidenceYou Might Be a Fit If You…Have 5+ years of experience building and scaling production systemsThrive in early-stage environments and enjoy wearing many hatsWrite clean, maintainable code and care about craftsmanshipThink in systems and design with an eye toward flexibility and resilienceTake ownership, act with urgency, and bias toward progress over perfectionAre energized by real-world complexity, data modeling, and automationWant to help define the future of engineering at ChestnutOur StackLanguages: Go, TypeScriptFrontend: React, TailwindInfra: K8s, ArgoCD, Kargo, Temporal, DagsterData: Postgres, Dynamo, SnowflakeBenefitsCompetitive salary and equity, with 10 year exercise window for stock optionsRemote-first culture built on trust, autonomy, and high performanceTeam offsites for all of us to bondTake what you need vacation policyTop notch health, dental, and vision insurance subsidized by us