Freelance Dating Site Chat Moderator Jobs (NOW HIRING)

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.

• 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.

• 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.