Voyage Operations Specialist Lead

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 Voyage Operations Specialist Lead supports the effective execution of booking and voyage operations processes across Guest Services. This role provides day-to-day direction and subject matter expertise to Operations Agents, helps ensure booking information is processed accurately and communicated efficiently to ships and internal teams.

This position also supports resolution of bookings, operational issues, and assists with quality control reporting, process documentation, system improvements, and irregular operations in partnership with the Operations Supervisor.

Full-time position available to work remotely as long as you live in one of these states:

AR, AZ, FL, LA, MN, TX, and WI.

Operational Leadership and Service Support 

• Provide day-to-day direction, guidance, and production oversight for Operations Agents.
• Oversee Operations inboxes to support timely responses and ensure information provided is accurate and consistent.
• Coordinate guest and travel advisor communications related to bookings, invoices, itinerary change notifications, and irregular operations.
• Review and approve or deny early disembarkation and late embarkation requests in accordance with established policies and procedures.
• Provide backup support for the main phone queue and lead line as needed.
• Support Vacation Planning management and complete other duties as assigned.

Process Documentation and Quality Control 

• Assign, create, review, and maintain standard operating procedures, Scribes, and other operational documentation.
• Ensure assigned SharePoint resources are accurate, current, and aligned with operational requirements.
• Maintain comprehensive operational records and support the accuracy and stability of system settings and booking data.
• Prepare ad hoc reports related to booking quality control and other operational processes.
• Identify workflow improvement opportunities and help implement process changes that increase efficiency and strengthen the guest experience.

Systems, Testing, and Change Management 

• Serve as the subject matter expert for D-Flo and HubSpot operational systems, including training, communications, and continuous improvement initiatives to drive efficiency, adoption, and business performance.
• Manage D-Flo and Travel communications including the transmission of letters and system improvements.
• Conduct user acceptance testing for new systems, processes, and operational enhancements to confirm that business requirements are met.
• Respond promptly to system issues, failures, and operational disruptions; coordinate with IT and management to support recovery and resolution.
• Promote thoughtful adoption of AI tools and emerging technologies by helping the team evaluate, implement, and adapt to new ways of working.
• Partner with Subject Matter Experts and Reservations management to improve systems and booking processes.

• 1+ years of contact center or reservations operations experience.
• Demonstrated experience overseeing teams with varied duties and skill levels.
• Intermediate to advanced proficiency in Microsoft Office (Excel, Word, Outlook, Teams), with the ability to train others on core usage.
• Experience in the travel, hospitality, or cruise industry strongly preferred.

Skills & Competencies:

• Strong understanding of booking lifecycle operations, reservations systems, and post-booking processing workflows.
• Proficiency with reservations and operations systems; experience with Seaware preferred.
• Strong written and verbal communication skills
• Excellent organizational and time management skills, with the ability to manage competing priorities in a fast-paced, evolving environment.
• A proactive, solution-oriented mindset — comfortable identifying problems and bringing forward recommendations without waiting to be asked.
• Deep familiarity with Windstar Cruises product, policy, and procedure (or the demonstrated ability to learn quickly).

Work Environment: This position works remotely. The work environment is home-office based, requiring reliable internet connectivity and the ability to participate in video meetings and collaborative digital workflows. This role requires the ability to work a varied schedule based on business needs, including early and late shifts and occasional weekends.

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.