Engineer - Agent Orchestration at Chestnut

Chestnut develops an AI-native operating system for insurance distribution, targeting the $1T+ insurance industry's sales and distribution spend. Backed by a16z, the company modernizes legacy systems with a flexible platform enabling carriers to automate workflows, optimize distribution spending, and drive growth. The platform is already contracted with major insurers experiencing expansion.

Small, high-context teams working with best-in-class tools achieve outsized results. The organization emphasizes AI-lean operations pursuing 10x productivity gains beyond headcount scaling.

What You'll Do

Design and build orchestration layers coordinating multiple AI agents performing complex enterprise workflows reliably

Develop systems managing agent-to-agent communication, task delegation, retrieval, and tool usage at scale

Translate cutting-edge AI techniques into production-ready capabilities

Ensure high reliability and fault tolerance in multi-agent systems for mission-critical insurance and compliance operations

Continuously improve workflow automation by identifying bottlenecks and engineering scalable solutions

Required Qualifications

3+ years engineering experience in growth-stage startups

Experience designing distributed systems or multi-service architectures

Strong backend engineering skills with applied AI systems interest

Understanding of reliability, consistency, and orchestration challenges in enterprise applications

Ability to thrive at the intersection of research and production engineering

Benefits: Competitive salary and equity (10-year exercise window), remote-first trust-based culture, team offsites, unlimited vacation, subsidized health/dental/vision insurance.