Chestnut | Hiring multiple roles (across engineering) | San Francisco + Seattle hubs (hybrid) | https://jobs.ashbyhq.com/Chestnut

Massive opp. Chestnut is the first AI-native operating system for insurance distribution management, tackling a $100B+ spend pool in the largest industry in the U.S. Legacy software and manual processes dominate this space; Chestnut is the only modern platform enabling real-time data, automation, and agentic AI workflows that directly grow carrier revenue.

Our stack: Go, TypeScript/React, Postgres, Temporal, K8s, Dagster, LLMs.

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We’re hiring:

** Forward Deployed Engineer – Work directly with customers to ship AI-powered workflows and integrations. https://jobs.ashbyhq.com/Chestnut/5d4fd1ec-60f3-4669-a2d2-31...

** Senior Software Engineer – Build core services, event-driven systems, and automation layers that scale. https://jobs.ashbyhq.com/Chestnut/fbbb7601-3d31-48b4-8639-75...

** Staff Software Engineer – Lead architecture and technical direction as we scale past enterprise workloads. https://jobs.ashbyhq.com/Chestnut/f28c5ee5-12aa-4e7b-b0ea-f5...

** Engineer [Agent Orchestration] – Focus on applied systems: multi-agent coordination, workflow automation, retrieval, and tool use. Bridge research to production and design orchestration layers for enterprise reliability. https://jobs.ashbyhq.com/Chestnut/075a0010-bfa5-489e-8808-e9...

** Engineer [ML + Agent Design] – Experiment with prompting, fine-tuning, and novel LLM techniques. Prototype new agent behaviors and push the boundaries of how models reason, interact, and automate in data-heavy domains. https://jobs.ashbyhq.com/Chestnut/0b6e2b45-fab9-47f2-8f10-30...

We’re also hiring for Product & Commercial Lead and Data + Infra roles (details on the site).

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You'll work on the bleeding edge - embedding enterprise-grade agentic AI at scale. We're looking for engineers who thrive in fast-paced environments and want to make a meaningful impact.

More info + apply: https://jobs.ashbyhq.com/Chestnut