Chat Lead

Windstar Cruises; Miami (FL); Hybrid; USD 52,000 - 76,000; Full time

Benefits offered by this job

Medical Insurance

Dental & Vision

HSA/FSA

Life & Disability Insurance

Paid Holidays

401(k) with Company Match

Education Assistance

Employee Discounts & Travel Deals

Job summary

Windstar Cruises is seeking a Chat Lead to own the digital chat channel, overseeing both AI-assisted and live agent conversations across guest inquiries. The role drives scripting, escalation triggers, and guest experience quality, maintaining Windstar’s 180 degrees from Ordinary service across every digital touchpoint.

This full-time, hybrid position can be based in the Miami metro area or remote from eligible US states.

Qualifications

• 2+ years in a contact center or customer service role; cruise or luxury travel experience preferred.
• Comfort with digital platforms and AI-assisted or chat-based service is a plus.
• Strong written communication and ability to reflect Windstar brand voice.

Responsibilities

• Own the chat queue across live and AI-assisted conversations with prompt, accurate responses.
• Monitor AI interactions in real time; optimize scripting and guest experience quality.
• Co-own the virtual agent with the AI Admin Lead; review performance and update content.
• Flag chat performance gaps and support platform configuration updates.
• Provide backup support for voice, outbound, and OCC during high volume.
• Maintain knowledge of itineraries, products, promotions, and policies to inform guests.
• Contribute to QA of chat transcripts; identify coaching opportunities.
• Assist onboarding and training of new agents on chat protocols and AI tools.
• Track team performance metrics and report trends to leadership.

Skills

2+ years contact center experience

AI-assisted chat experience

Strong written communication

Brand voice alignment

Multitasking across chats

Team player

CRM tools familiarity

Tools

CRM tools

Job description

Overview (Text Only)

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 (Text Only)

• 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 (Text Only)

• 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:

• 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.