Engineer - ML + Agent Design

Summary

Join Chestnut, a company building an AI-native operating system for insurance distribution, and help transform the $1T+ insurance industry. Backed by a16z, we are replacing legacy systems with a modern platform to automate workflows, optimize distribution, and unlock growth. We're seeking a skilled Machine Learning Engineer to develop and refine ML pipelines for agent behaviors using various techniques like prompting, fine-tuning, and reinforcement learning. You will prototype and experiment with novel agent reasoning and build data pipelines and evaluation frameworks. Collaboration with orchestration and infra teams is crucial to ensure robust and scalable agent models. This is a unique opportunity to modernize the infrastructure of a vital industry and contribute to a generational platform shift.

Requirements

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

Responsibilities

• Develop and refine ML pipelines for agent behaviors using prompting, fine-tuning, retrieval-augmented generation, and reinforcement learning techniques
• 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

Preferred Qualifications

• Enjoy blending research and engineering to push agent capabilities forward
• Thrive in fast-paced environments where prototypes quickly evolve into production systems

Benefits

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