Engineer - Agent Orchestration

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.