Windstar Cruise Line 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 OCC Fleet Manager is the onboard commercial operations leader for Windstar Cruises' Onboard Cruise Consultant program, responsible for the performance, development, and implementing the strategic direction of OCCs across the fleet. This is a highly mobile, field-based management role that requires frequent travel to Windstar's yachts throughout the year, including on short notice, to provide hands-on leadership, conduct training, evaluate performance, and ensure the OCC program is operating at the highest standard. The OCC Fleet Manager owns the program's revenue targets, drives incremental onboard sales, and serves as the primary integrator of current and incoming technologies into the OCC workflow. This position reports directly to the Senior Director of Vacation Planning and is a critical link between shipboard sales execution and the company's broader commercial strategy.

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.

• Manage the full OCC team across the Windstar fleet, including performance management, coaching, professional development, and accountability to revenue and service standards.
• Own OCC program revenue targets, tracking performance by vessel and individual, identifying trends, and taking proactive action when results deviate from plan.
• Travel to the fleet throughout the year to provide in-person leadership, conduct performance reviews, deliver training, and assess the onboard guest experience; must be available to deploy with less than 72 hours notice when operational needs arise.
• Provide contract gap coverage as needed, stepping into an active OCC role aboard a yacht when a position is unfilled, to maintain continuity of the guest experience and revenue program.
• Lead the integration of current and incoming technologies into the OCC workflow, including AI-assisted tools, booking platforms, and guest engagement systems, ensuring the fleet stays current and OCCs are proficient.
• Develop and deliver OCC training programs covering product knowledge, sales techniques, guest interaction standards, promotional execution, and technology tools.
• Partner with the Senior Director to define OCC program strategy, set seasonal goals, and align onboard sales priorities with broader Vacation Planning and commercial objectives.
• Recruit, onboard, and evaluate OCC talent; maintain a pipeline of qualified candidates to ensure fleet coverage and minimize gaps.
• Serve as the primary point of escalation for OCC-related guest concerns, shipboard operational issues, and contract or scheduling challenges.
• Report regularly to the Senior Director on fleet-wide OCC performance, revenue results, training progress, technology adoption, and program health.
• Process monthly OCC incentive reporting for submission to HR and payroll.
• Collaborate with the contact center team to ensure a seamless guest experience across onboard and shore-side touchpoints, sharing insights that improve both channels.
• Other duties as assigned.

• Direct experience working as an Onboard Cruise Consultant or in a comparable shipboard guest-facing sales role is required.
• Background in travel industry sales, luxury hospitality, or cruise operations; familiarity with the small-ship or yacht segment is strongly preferred.
• Demonstrated sales performance with accountability to revenue targets; experience managing or mentoring a sales team preferred.
• Ability and genuine willingness to travel frequently and on short notice — including international travel to ports of call across Windstar's global itinerary portfolio.
• Comfort operating independently in a remote, shipboard environment with limited day-to-day access to shore-side leadership.
• Proficiency with technology tools used in a modern contact center or onboard sales environment; enthusiasm for learning and deploying new platforms, including AI-assisted tools.
• Strong interpersonal and coaching skills; able to build trust with OCCs across a distributed, rotating fleet while holding the team to a high standard.
• Excellent verbal and written communication skills; able to represent the Windstar brand with polish in guest-facing and leadership-facing settings.
• Highly organized and self-directed with the ability to manage scheduling, travel logistics, performance documentation, and reporting across multiple vessels simultaneously.
• Valid passport required; willingness to meet any visa, vaccination, or port entry requirements associated with Windstar's global fleet deployment.

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.

• Direct experience working as an Onboard Cruise Consultant or in a comparable shipboard guest-facing sales role is required.
• Background in travel industry sales, luxury hospitality, or cruise operations; familiarity with the small-ship or yacht segment is strongly preferred.
• Demonstrated sales performance with accountability to revenue targets; experience managing or mentoring a sales team preferred.
• Ability and genuine willingness to travel frequently and on short notice — including international travel to ports of call across Windstar's global itinerary portfolio.
• Comfort operating independently in a remote, shipboard environment with limited day-to-day access to shore-side leadership.
• Proficiency with technology tools used in a modern contact center or onboard sales environment; enthusiasm for learning and deploying new platforms, including AI-assisted tools.
• Strong interpersonal and coaching skills; able to build trust with OCCs across a distributed, rotating fleet while holding the team to a high standard.
• Excellent verbal and written communication skills; able to represent the Windstar brand with polish in guest-facing and leadership-facing settings.
• Highly organized and self-directed with the ability to manage scheduling, travel logistics, performance documentation, and reporting across multiple vessels simultaneously.
• Valid passport required; willingness to meet any visa, vaccination, or port entry requirements associated with Windstar's global fleet deployment.

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.