Director of Engineering – AI Agents (Insurance Domain-Specific Automation)

Director of Engineering – AI Agents

San Francisco, CA (onsite)

Up to $450K + Equity

Visa and relocation packages available

My client is a well-funded Series A startup backed by prominent investors, including a16z and Y Combinator, currently building domain-specific AI agents to automate complex workflows for the insurance industry.

Their AI Assistant automates complex workflows like submission intake, policy comparisons, and underwriting audits—making teams faster, smarter, and more efficient. Leading insurers, reinsurers, MGAs, and brokers rely on our technology to drive better decisions at scale.

The company is led by an elite team of founders and engineers from top-tier organizations and offers the opportunity to own the entire AI division. Responsible for people management, hiring, and building the agentic AI product.

Based in San Francisco with strong comp $350k-$450k

We are looking for a Director of Engineering - AI Agents with 7+ years of experience to own and scale our AI organization (currently 8 people). You'll lead the team building production LLM-powered agents that automate critical workflows in the trillion-dollar insurance industry. This is a rare opportunity to join a fast-growing, a16z-backed startup as the engineering leader who shapes the technical direction of the entire AI org. Both founders are engineers, and you'll have an outsized say on product direction while building your team from the ground up.

What will you be doing?

• Own and grow the AI org, scaling it into three teams: AI infrastructure (routing & reliability), Agent intelligence (evals, shared tools, multimodal pipelines), and Agentic products (customer-facing AI assistant, long-running workflows)
• Set technical direction for building agents that hold up in real production on real customer money — including model routing, multi-agent orchestration, and reliability
• Recruit, mentor, and retain a world-class team of AI engineers, hiring the leaders beneath you as the org scales post-Series A
• Stay deeply technical — still in the code and architecture, setting the bar by example
• Push the frontier of what AI agents can do for insurance as the field evolves

Requirements:

• 7+ years of experience in AI/ML engineering and managing teams at a top tech firm
• Led AI/ML team that shipped production LLM/agent systems

Discover our full range of relocation jobs with comprehensive support packages to help you relocate and settle in your new location.

• Built and scaled an engineering team of 10+
• Experience at early- stage or high- growth B2B SaaS startup
• CS or related technical degree from top- tier university
• Still a hands- on coder, especially with agentic architectures (tool use, planning, multi- agent orchestration, evals)
• Still writes and reviews code; can evaluate experiment design
• Experience with model routing, reliability, and multimodal pipelines
• Passionate about leadership; eager to source, mentor, and manage team of engineers
• Clear, concise communicator and writer
• Must be based in or willing to relocate to San Francisco (on- site)
• Founder's mindset — high ownership, thrives in fast- paced environments

This is a rare opportunity to join a fast-growing, a16z-backed startup as the engineering leader who shapes the technical direction of the entire AI org – if this sounds like you apply today!