Head of AI Engineering

Who We Are

Faye is the first-ever digital, consumer-centric travel insurance for Americans with a product redefining travel coverage and care, taking it from a forgettable add-on to a must-have advantage that enhances the entire trip experience. Faye’s whole-trip protection, coupled with its proprietary technology, enables 24/7 immediate assistance, claims processing and reimbursements anywhere in the world, setting a new standard and over-delivering in an industry synonymous with doing the opposite.

Life at Faye

At Faye, every day is a journey. Whether you’re building the next generation of travel products, coding new solutions, or helping travelers navigate the unexpected, your work here has a real impact on real people. Our team is as diverse as the destinations our travelers explore–made up of 62% women, 50% parents, and a few office pets. Since launching in 2022, we’ve accomplished what others in the travel insurance industry only dream of–and we’re just getting started. At Faye, we believe in growing together, having fun along the way, and making every day count.

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.

Responsibilities:

• 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.

Requirements:

• 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.