Head of AI Engineering

Who we are

Faye is the fastest-growing travel protection company in the U.S., and the highest-rated by travelers who use it trip after trip.

We’ve raised $100M to build the autonomous platform for traveler care: insurance, travel care, real-time information, and finance in one place, powered by AI and a team that moves fast.

We’re there for travelers throughout their entire journey, from the moment they book to the moment they’re back home.

The bar is a 6-star experience, 24/7: near-instant payouts, an award-winning app and real support when travel goes sideways. It’s hard to pull off. That’s the point.

Come build what’s next with us.

What we're looking for

As Head of AI Engineering, you'll own how AI work is structured, prioritized, and managed across Faye - turning scattered, fast-moving efforts into a coordinated, scaled capability. You'll set the technical direction for how we build with GenAI and agentic systems, continuously scout the external ecosystem for what gives us an edge, and partner with platform engineering to make sure the infrastructure scales with demand.

This is equal parts strategy, organization, and technical judgment. You'll take ambiguous, high-level vision and turn it into execution - aligning teams and resources to business goals, and translating complex AI roadmaps for executives. You'll report to the CTO and work closely with leaders across R&D, Ops, CX, and Claims.

• Establish how AI initiatives are prioritized, staffed, coordinated, and delivered across various departments, bringing ownership and order to a fast-moving space.
• Continuously assess external GenAI tools, platforms, and vendors; make build-vs-buy calls; and bring the best of what's out there into Faye.
• Guide how Faye designs prompts, context layers, tools, and guardrails to make agentic orchestration reliable in production.
• Ensure that across the company there are formal and informal education initiatives, many of which you will own or lead yourself.
• Ensure the core AI foundations: serving, retrieval, evaluation, observability, and reliability - scale with the business.
• Translate high-level vision into a sequenced roadmap, align resources to the highest-impact priorities, and measure outcomes against business goals.
• Identify internal needs across teams, and articulate complex AI roadmaps clearly to non-technical, global executives.
• Build the guardrails and governance around how the company works with AI.

• 6+ years managing technical teams or individuals.
• 2+ years of hands-on experience leading or driving GenAI initiatives, with a deep understanding of LLMs, prompt engineering, RAG, agentic systems, and modern AI tooling.
• Background in DevOps and product - understanding both how systems are built and operated and how products create value.
• Track record of taking full ownership of ambiguous initiatives and independently turning a high-level vision into execution.
• Track record of scaling engineering/innovation groups, aligning resources with business goals, and working with platform engineering at scale.
• Experience working in global SaaS companies and the ability to thrive in fast-paced, evolving environments with rapid development cycles and agile methodologies.
• Experience in a regulated domain (insurance, fintech, healthcare) - an advantage.