Software Engineer (Senior-Level)
Chestnut · San Francisco
About this role
## About Chestnut Chestnut is building the first **AI-native operating system** for insurance distribution—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 distribution dollars**, and **unlock new growth**. We’re scaling with urgency and building the data model and context layer needed to make agentic AI practical in the real world. ## Engineering at Chestnut We build modern infrastructure for **AI-driven insurance operations**: 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 (Senior-Level)**, 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 our technical culture as we grow. ## What You’ll Do - **Lead** the design and development of core systems — from **Go microservices** and **event-driven workflows** to **React UIs** and automation layers - **Partner cross-functionally** to scope, prioritize, and deliver high-impact features that drive real business outcomes - **Own architecture and implementation** end-to-end, ensuring long-term scalability and reliability - Contribute to and evolve core infrastructure, including **observability**, **permissions**, and **developer experience** - Set the bar for technical excellence through **mentoring**, improving processes, and helping us scale with confidence ## You Might Be a Fit If You… - Have **5+ years** of experience building and scaling production systems - Thrive in early-stage environments and enjoy wearing many hats - Write clean, maintainable code and care about craftsmanship - Think in systems and design for flexibility and resilience - Take ownership, act with urgency, and **bias toward progress** over perfection - Are energized by real-world complexity, data modeling, and automation - Want to help define the future of engineering at Chestnut ## Our Stack - **Languages:** Go, TypeScript - **Frontend:** React, Tailwind - **Infra:** K8s, ArgoCD, Kargo, Temporal, Dagster - **Data:** Postgres, Dynamo, Snowflake ## Benefits - Competitive salary and equity, with a **10-year exercise window** for stock options - **Remote-first** culture built on trust, autonomy, and high performance - Team offsites - Flexible **vacation policy** (take what you need) - Top-tier **health, dental, and vision** insurance subsidized by us
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