Supervisor of Operations

Windstar Cruises, awarded World’s Best Small Ship Cruise line, offers intimate yacht-style experiences and unique voyages to the world’s best small ports and hidden harbors. Our fleet of three sailing yachts and four all-suite yachts carries 148 to 342 guests, delivering personalized and immersive travel experiences. Our mission is to enrich lives through inspired travel with values centered on being guest-obsessed, open, fun-loving, genuine, polished, and responsible.

About the role

We are seeking a Supervisor of Operations to play a critical leadership role within the Vacation Planning department. This position oversees the day-to-day performance, development, and operational excellence of the Operations team, managing the full booking lifecycle—from reservation creation through voyage close—while ensuring accuracy, efficiency, and a seamless guest experience. As Windstar advances its contact center modernization, this role will serve as a key operational steward, partnering with the AI & Technology team to support AI-assisted workflows, train staff, and identify automation opportunities that elevate team capacity without compromising luxury service standards.

This is a hands-on leadership role combining tactical oversight with a forward-looking mindset, ideal for someone who can manage today’s booking operations while contributing to the future of the department. Full-time, hybrid position available in the Miami metro area or remotely in AR, AZ, FL, LA, MN, TX, or WI.

Responsibilities

• People Leadership & Team Development
  • Lead, coach, and develop the Operations team to deliver accurate, high-quality booking processing aligned with company KPIs and service standards.
  • Partner with Guest Services Management and HR on recruitment, onboarding, performance evaluations, and improvement planning.
  • Build a positive, accountable team culture supporting individual growth and collective performance, including ongoing skill development.
  • Deliver training and continuing education on new systems, AI tools, and updated workflows.
  • Monitor individual and team performance, providing real-time coaching and structured improvement plans as needed.
• Operations Execution & Booking Oversight
  • Oversee end-to-end booking processing from reservation creation through voyage close, ensuring accuracy across documentation, invoicing, manifests, accounting, and communications.
  • Coordinate across departments—Reservations, Groups, Accounting, Air, and shipboard teams—to facilitate smooth booking and voyage operations.
  • Maintain oversight of Irregular Operations and Redeployments, ensuring timely communication and resolution for affected guests and internal teams.
  • Support creation, organization, and archiving of operational communications including Itinerary Change Notifications, Charter Moves, and Irregular Operations letters.
  • Coordinate phone and email coverage to ensure operational continuity, and provide backup support to the main queue and lead lines as needed.
  • Ensure operations procedures, policies, and reference materials are current, clearly documented, and accessible on the Guest Services intranet and company systems.
• AI Integration & Technology Stewardship
  • Partner with the AI Lead to support adoption and effective use of AI-assisted tools, including workflow automation and intelligent booking support.
  • Serve as an operational champion for new technology implementations, translating system changes into team-ready training and documentation.
  • Proactively identify repetitive, manual, or high-volume tasks suitable for automation or AI augmentation, and surface recommendations to management.
  • Support the team in building comfort and proficiency working alongside AI tools, ensuring staff understand where human judgment remains essential.
  • Collaborate with the Cresta AI Admin Lead and technology partners (Seaware and other integrated systems) to provide operational input on system enhancements.
• Reporting, Analysis & Process Improvement
  • Provide management with regular reporting on team performance, processing volumes, quality metrics, and operational trends.
  • Identify process gaps and inefficiencies, recommending and implementing solutions to improve throughput, accuracy, and guest experience.
  • Lead or contribute to project management initiatives related to operations systems, database maintenance, and workflow development.
  • Support cross-functional initiatives as directed by the Manager of Operations, including departmental planning, audits, and special projects.

Requirements

• 2+ years of contact center or reservations operations experience in roles of increasing responsibility.
• 1+ year of direct supervisory or team lead experience preferred.
• Demonstrated experience managing teams with varied duties and skill levels.
• Experience in the travel, hospitality, or cruise industry strongly preferred.

Skills

• Strong understanding of booking lifecycle operations, reservations systems, and post-booking processing workflows.
• Proficiency with reservations and operations systems; experience with Seaware preferred.
• Comfort working with AI-assisted tools and curiosity about how technology can improve operational performance; prior experience with AI platforms, CRM automation, or workflow tools is a plus.
• Intermediate to advanced proficiency in Microsoft Office (Excel, Word, Outlook, Teams), with the ability to train others on core usage.
• Strong written and verbal communication skills; able to communicate clearly with frontline staff, cross-functional partners, and senior leadership.
• 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.
• Deep familiarity with Windstar Cruises product, policy, and procedure (or the demonstrated ability to learn quickly).

Benefits

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