Supervisor of Operations

Overview

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.

We are currently seeking a Supervisor of Operations to play a critical leadership role within the Vacation Planning department, oversee the day-to-day performance, development, and operational excellence of the Operations team. This position is responsible for managing the full booking lifecycle - from reservation creation through voyage close - while ensuring accuracy, efficiency, and a seamless guest experience at every touchpoint.

As Windstar Cruises advances its contact center modernization, this role will serve as a key operational steward of that transformation. The Supervisor of Operations will work at the intersection of people, process, and technology - partnering closely with the AI & Technology team to support the deployment of AI-assisted workflows, ensuring the team is trained and equipped to work alongside intelligent tools, and helping to identify automation opportunities that elevate team capacity without compromising the luxury service standard Windstar is known for.

This is a hands-on leadership role that combines tactical oversight with a forward-looking mindset - a leader who can manage today's booking operations while actively contributing to the future state of the department.

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, CO, FL, LA, MN, TX, and WI.

Responsibilities

People Leadership & Team Development

• Lead, coach, and develop the Operations team to consistently deliver accurate, high-quality booking processing in alignment with company KPIs and service standards.
• Partner with Guest Services Management and HR on recruitment, onboarding, performance evaluations, and improvement planning for Operations staff.
• Build a positive, accountable team culture that supports individual growth and collective performance, including ongoing skill development as the department evolves.
• Deliver training and continuing education for the team, including onboarding to new systems, AI tools, and updated workflows as they are introduced.
• 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 - including 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 that 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 the adoption and effective use of AI-assisted tools across the Operations team, including workflow automation and intelligent booking support.
• Serve as an operational champion for new technology implementations - translating system changes into team-ready training, clear documentation, and confident adoption.
• Proactively identify repetitive, manual, or high-volume tasks within the operations workflow that are candidates 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 and oversight remain essential.
• Collaborate with the Cresta AI Admin Lead and relevant technology partners (Seaware and other integrated systems) to provide operational input on system enhancements and flag issues impacting booking accuracy or throughput.

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 helping to implement solutions that improve throughput, accuracy, and the 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.

Qualifications

Experience

• 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 & Competencies

• 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 genuine 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 without waiting to be asked.
• Deep familiarity with Windstar Cruises product, policy, and procedure (or the demonstrated ability to learn quickly).

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.