Voyage Operations Specialist Lead

About the role

Windstar Cruises is the award-winning “World’s Best Small Ship Cruise Line,” known for intimate yacht-style experiences and unique voyages to the world’s best small ports and hidden harbors. Our three sailing yachts and four all-suite yachts carry just 148 to 342 guests and cruise around the globe. We enrich people’s perspectives through inspired, 180 degrees-from-ordinary travel.

Responsibilities

• Operational Leadership and Service Support
  • Provide day-to-day direction, guidance, and production oversight for Operations Agents.
  • Oversee Operations inboxes to ensure timely, accurate, and consistent responses.
  • Coordinate guest and travel-advisor communications on bookings, invoices, itinerary changes, and irregular operations.
  • Review and approve or deny early disembarkation and late-embarkation requests per policy.
  • 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.
  • Keep assigned SharePoint resources 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 on booking quality control and other operational processes.
  • Identify workflow improvements and help implement 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.
  • Manage D-Flo and Travel communications, including transmission of letters and system improvements.
  • Conduct user-acceptance testing for new systems, processes, and operational enhancements to confirm 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.

Qualifications

• 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 remote role is home-office based, requiring reliable internet connectivity and the ability to participate in video meetings and collaborative digital workflows. The schedule varies based on business needs, including early and late shifts and occasional weekends.

Benefits

• Medical, Dental & Vision coverage
• HSA & FSA options
• Life & Disability insurance
• Accident, Hospital & Critical Illness coverage
• Pet Insurance
• Vacation, Sick Time and paid Holidays
• 401(k) with Company Match
• Employee Assistance Plan
• Education Assistance
• Employee Discounts & Travel Deals