Contact Center AI Lead

## Overview **Awarded World’s Best Small Ship Cruise line, Windstar Cruises is known for intimate yacht style experience and unique voyages to the world’s best small ports and hidden harbors. Its three sailing yachts and four all-suite yachts carry just 148 to 342 guests and cruise around the world. Our mission is to imagine and deliver personalized and immersive experiences 180 degrees from ordinary. We enrich people’s perspective through inspired travel.** **Our Mission**: Enriching Lives Through Travel **Our Values**: Guest Obsessed, Open and Inviting, Fun-Loving and Focused, Light-Hearted and Genuine, Casual Yet Polished, Safe and Responsible. **Job Summary:** The Contact Center AI Lead supports the Training Supervisor in the day-to-day administration and upkeep of Windstar Cruises' contact center AI platform. This role is a hands-on contributor responsible for maintaining the accuracy, quality, and effectiveness of AI-assisted tools used across the full Vacation Planning team. In addition to internal platform support, the Contact Center AI Lead shares co-ownership with the Chat Lead of the guest-facing virtual agent, monitoring its performance, maintaining its content, and ensuring it consistently delivers an experience that reflects Windstar's brand standard. The Contact Center AI Lead is also a standing participant in the company's broader AI initiatives, providing operational insight and front-line perspective as new capabilities are evaluated, piloted, and deployed across the contact center. ## Responsibilities - Assist the Training Supervisor with the ongoing administration of the contact center AI platform, executing content updates, scripting revisions, and configuration changes as directed. - Maintain AI knowledge bases, response libraries, and escalation logic to ensure accuracy across the full range of guest inquiries handled by the Vacation Planning team. - Serve as a first-line resource for agents across the contact center who have questions about AI tool functionality, escalating platform issues to the Training Supervisor as needed. - Coordinate with the Training Supervisor and technology partners to log, prioritize, and follow up on platform issues or enhancement requests. - Co-own the performance and content of the guest-facing virtual agent alongside the Chat Lead, ensuring the tool delivers accurate, on-brand responses that reflect Windstar's guest experience standard. - Monitor virtual agent interactions for accuracy, tone, escalation behavior, and guest experience quality; surface issues and coordinate corrections with the Training Supervisor and Chat Lead. - Maintain and update virtual agent content in response to itinerary changes, policy updates, promotional launches, and seasonal shifts in guest inquiry patterns. - Partner with the Chat Lead to review guest feedback and chat data, translating insights into scripting improvements and escalation logic refinements. - Participate actively in ongoing AI initiatives across the contact center, including tool evaluations, pilot programs, and capability expansions, providing operational perspective and front-line feedback. - Support the testing and documentation of new AI features or platform enhancements prior to team-wide rollout. - Help identify opportunities where AI tooling could further support team efficiency, guest experience, or compliance and bring those ideas forward to the Training Supervisor. - Stay current on developments in contact center AI, virtual agent technology, and hospitality industry applications to inform ongoing improvement efforts. - Monitor AI-assisted interactions across all contact center functions, flagging errors or recurring performance gaps to the Training Supervisor for review and action. - Assist with tracking and compiling AI performance data, including interaction volumes, escalation rates, and resolution accuracy, to support the supervisor's reporting to leadership. - Help develop and maintain agent-facing job aids, qu…