Chestnut is hiring an Engineer focused on ML and Agent Design to build AI-driven insurance operations. You will develop ML pipelines and novel agent reasoning, moving from prototype to production in complex, data-heavy domains.

What You'll Do

Develop and refine ML pipelines for agent behaviors using prompting, fine-tuning, retrieval-augmented generation, and reinforcement learning.
Prototype and experiment with novel agent reasoning, multi-step planning, and tool usage for complex, data-heavy domains.
Run structured experiments to evaluate agent performance, optimize reasoning and retrieval, and translate findings into production-ready solutions.
Build data pipelines and evaluation frameworks that support rapid iteration and deployment of new agent capabilities.
Collaborate with orchestration and infra teams to ensure agent models are robust, scalable, and reliable in production.

What We're Looking For

3+ years of experience building and analyzing ML systems, including data pipelines and training frameworks.
Strong experience with LLMs, prompting, fine-tuning, and ML experimentation.
Understanding of retrieval systems, vector databases, and reasoning techniques for large-scale text datasets.

Team & Environment

You'll join small, high-context teams working with best-in-class tools and colleagues to achieve outsized results. We chase 10x productivity gains that allow us to scale impact beyond our headcount.

Benefits & Compensation

Competitive salary and equity, with 10 year exercise window for stock options.
Remote-first culture built on trust, autonomy, and high performance.
Team offsites and a take what you need vacation policy.
Top notch health, dental, and vision insurance subsidized by us.