Software Engineer (Mid-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 required to make agentic AI practical in real insurance operations. ## Engineering at Chestnut We build modern infrastructure for **AI-driven insurance operations**—including 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 (Mid-Level)**, you’ll join a high-agency, cross-functional team focused on delivering impactful features quickly. You’ll work across the stack, contribute to system design, and help shape our technical culture as we grow. ## What you’ll do - Build the backbone of our AI-native platform—from **Go services** and **event-driven workflows** to **React UIs** and automation layers - Partner with product and design to ship fast, learn quickly, and iterate on high-impact features - Own your work end-to-end—from architecture to deployment, with clear handoffs and strong accountability - Scale the foundation: **observability**, **permissions**, and **developer tooling** - Move like a builder: stay unblocked, act with urgency, and focus on what matters most ## You might be a fit if you… - Have **3+ years** building and scaling production systems with **Go**, **TypeScript**, and **React** - Have strong CS fundamentals and build systems that last - Have hands-on experience with **gRPC**, **event-driven architecture**, and **clean, versioned APIs** - Are fluent in containers and modern orchestration tools like **Temporal**, **Dagster**, and **ArgoCD** - Thrive in fast-paced, high-agency environments and can navigate tradeoffs - Are curious about AI and motivated to shape foundational systems in a massive industry ## 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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