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
We are seeking a visionary lead to redefine the strategy and direction of our customer-facing functions. The Head of Customer Experience Strategy & Enablement position is not just about managing current operations, but about architecting a technology-driven organization that anticipates the needs of 2027 and beyond. You will oversee the evolution of customer support through the lens of AI integration while maintaining the high-touch, critical care required for complex medical and travel cases.
Responsibilities- Innovative Strategy: Lead the transition from traditional CX models to an AI-first approach that transforms how we interact with customers.
- Operational Excellence: Manage a dual-layer workforce consisting of human team leaders and virtual/AI agents.
- Complex Logistics Management: Ensure seamless CX delivery within our unique space, including handling complex medical evacuations.
- Cross-Functional Collaboration: Bridge the gap between Customer Experience and the Claims department to ensure smooth hand-offs.
- Tooling & Discipline: Ground futuristic strategies in existing disciplines while identifying and implementing the next generation of CX tools.
- 5+ years of experience leading large-scale CX, claims or call center operations, with expertise in omni-channel B2C environments.
- Proven track record of leveraging automation/AI, scaling teams and managing global operations with a tech-driven approach.
- Extensive experience in developing long-term customer experience strategies and a proven track record of improving efficiency through metrics.
- Able to work in-office.
- Data-driven mindset, with experience implementing tech solutions that scale CX and/or claims operations.
- Ability to manage flexible time zones and remain available to address urgent customer issues during non-standard hours when needed.
- Excellent communication skills, a proactive leadership style, and a deep understanding of customer behavior, expectations, and satisfaction drivers, with a passion for customer service and a commitment to continuous improvement.
- Startup experience is highly preferred; experience in industries like insurtech, travel, or fintech is a big plus.
Skills Required
- 5+ years leading large-scale CX, claims, or call center operations in omni-channel B2C environments
- Proven track record leveraging automation and AI to scale teams and operations
- Experience managing global operations and cross-functional collaboration between CX and claims
- Demonstrated ability to develop long-term customer experience strategies and improve efficiency using metrics
- Able to work in-office
- Data-driven mindset with experience implementing tech solutions that scale CX or claims operations
- Ability to manage flexible time zones and be available during non-standard hours when needed
- Excellent communication and proactive leadership, deep understanding of customer behavior and satisfaction drivers
- Startup experience; experience in insurtech, travel, or fintech
Faye (withfaye.com) Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Faye (withfaye.com) and has not been reviewed or approved by Faye (withfaye.com).
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Leave & Time Off Breadth — Feedback suggests 20 days of PTO has been highlighted positively. This points to a relatively robust time-off offering.
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Affordable Benefits — Feedback suggests fully paid benefits have been cited, reducing out-of-pocket costs. This implies the benefits package may be financially accessible.
Faye (withfaye.com) Insights
What We Do
Named a TIME Best Invention of 2025, a Top 25 Hot Travel Startup of 2025 by PhocusWire, a Top 50 Insurtech Startup Globally in 2025 by CB Insights, one of the Best Travel Insurance Companies by The Wall Street Journal, and a LinkedIn Top Startup of 2025. Faye is award-winning travel insurance that provides whole-trip travel coverage and care to bring out the best in each journey with industry-leading technology that enables smarter, faster, smoother assistance and claims resolutions. Our robust travel insurance covers your health, your trip, your stuff, and even your pet, via an app that provides real-time proactive solutions, quick reimbursements and 24/7 customer experience specialists who turn travel mishaps into laugh-about-it-later memories. Join our team of travel and insurance experts as we set a new standard by overdelivering in an industry oftentimes synonymous with doing the opposite.
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