Chat Lead

XANTERRA TRAVEL COLLECTION; Miami (FL); Hybrid; USD 55,000 - 75,000; Full time

Benefits offered by this job

Medical, Dental & Vision

401(k) with Company Match

Travel Discounts

Job summary

Windstar Cruises in Miami area seeks a Chat Lead to own the chat channel, combining AI-assisted interactions with live agent conversations, and drive the guest experience across digital touchpoints. This full-time, hybrid role offers opportunities to shape service delivery in a luxury travel context.

You will monitor AI interactions, collaborate with the AI Admin Lead, and support onboarding and training while maintaining up-to-date itinerary knowledge and policies to deliver personalized, 180

Qualifications

• 2+ years in contact center or customer service; cruise or luxury travel preferred.
• Strong written communication and brand voice across digital channels.
• Comfort with digital tools and AI-assisted or chat-based service experience a plus.
• Ability to multitask across multiple chats while maintaining guest-first mindset.
• Collaborative team player with flexibility to support voice channels when needed.

Responsibilities

• Own the chat queue as the primary channel with prompt, brand-aligned responses.
• Monitor AI agent interactions in real time and optimize scripts and escalation triggers.
• Co-own the guest-facing virtual agent with the AI Admin Lead and update content as needed.
• Support platform configuration updates and address chat performance gaps.
• Provide backup support for voice channels during high-volume periods.
• Maintain up-to-date knowledge of itineraries, promotions, and policies for accurate guest info.
• Contribute to onboarding and training of new chat agents.

Skills

Customer service

Digital communication

Written communication

Multitasking

Team collaboration

Tools

CRM tools

AI-assisted platforms

Job description

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 Chat Lead serves as the primary point of ownership for Windstar Cruises' digital chat channel, including both AI-assisted virtual interactions and live agent conversations. This role plays a central part in the contact center's technology-forward future state, acting as a subject matter expert for chat-based guest engagement and supporting the broader team's transition toward AI-augmented service delivery. The Chat Lead maintains the Windstar standard of personalized, 180 degrees from Ordinary guest experiences across every digital touchpoint.

Full-time position available to work in a hybrid-model from Miami metro area, or remotely as long as you live in one of these states: AR, AZ, FL, LA, MN, TX, and WI.

Responsibilities

• Own the chat queue as primary channel, ensuring prompt, accurate, and brand-aligned responses to guest inquiries across live and AI-assisted conversations.
• Monitor AI virtual agent interactions in real time, identifying opportunities to optimize scripting, escalation triggers, and guest experience quality.
• Co‑own the guest‑facing virtual agent alongside the AI Admin Lead, reviewing performance, providing front‑line feedback, and coordinating content updates that reflect live guest inquiry trends.
• Partner with the AI Admin Lead to flag chat‑specific performance gaps, suggest workflow improvements, and support platform configuration updates.
• Serve as backup support for inbound voice, outbound, and OCC (Onboard Cruise Consultant) functions during high‑volume periods.
• Maintain up‑to‑date knowledge of Windstar's itineraries, yacht products, promotions, and policies to provide accurate and compelling guest‑facing information.
• Support quality assurance review of chat transcripts, identifying coaching opportunities and escalating recurring issues to the supervisor.
• Contribute to the onboarding and training of new agents on chat protocols, digital service standards, and AI‑assisted tools.
• Track and report on personal and team chat performance metrics; proactively identify trends requiring leadership attention.
• Other duties as assigned.

Qualifications

• 2+ years of experience in a contact center or customer service role; cruise or luxury travel experience preferred.
• Demonstrated comfort with digital communication platforms and emerging technology tools; experience with AI‑assisted or chat‑based service is a plus.
• Strong written communication skills with the ability to represent the Windstar brand voice across digital channels.
• Ability to multitask across simultaneous chat interactions while maintaining accuracy and a guest‑first mindset.
• Collaborative team player with flexibility to support voice channels when needed.
• Proficiency in standard contact center CRM tools; familiarity with AI‑assist platforms is an advantage.

Benefits

For full‑time employees, Windstar offers a comprehensive benefits package including: Medical, Dental & Vision; HSA & FSA; Life & Disability; Accident, Hospital & Critical Illness; Pet Insurance; Vacation, Sick Time and paid Holidays; 401(k) with Company Match; Employee Assistance Plan; Education Assistance and Employee Discounts & Travel Deals.

EEO

Windstar is committed to a diverse and inclusive workplace. We are an equal opportunity employer. Qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity or expression, national origin, age, disability, pregnancy, genetic information, protected veteran status, or any other legally protected status.