Sailing Program Director Jobs in Florida (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.

We are currently seeking a Director, Fleet Planning & HR Operations. This cultural leader is the operational backbone of Windstar's crew organization - responsible for the strategy, systems, and people that keep our fleet fully crewed, compliant, and thriving. This role owns end-to-end crew lifecycle management, fleet workforce planning, and regulatory compliance across MLC, ILO, flag state, and CBA frameworks, while fostering the engaged crew culture that defines the Windstar guest experience.

• Develop, maintain, and enforce HR policies and SOPs that meet or exceed MLC, ILO, flag state, and applicable maritime labor standards - keeping Windstar audit-ready at all times.
• Lead CBA negotiations and administer collective bargaining agreements; maintain productive, ongoing relationships with union partners including Nautilus, KPI, AMOSUP, and the ITF.
• Oversee full-cycle crew recruitment, payroll, compensation, and benefits programs, ensuring alignment with fleet operational needs, CBA terms, and budgetary targets.
• Direct the Fleet Planning function, driving workforce forecasting, crew scheduling, and deployment strategies that keep every vessel properly staffed across all voyages and itineraries.
• Lead the Crew Engagement & Welfare team and the Office Manager, championing crew wellbeing programs, recognition initiatives, and a shipboard culture where people genuinely want to stay and grow.& Welfare team and oversee the Office Manager
• Manage global manning agency partnerships and crew medical oversight, balancing quality standards, regulatory compliance, and cost-effectiveness across sourcing regions.
• Administer and optimize crew management systems, including Adonis and Brightwell, maintaining data integrity and identifying opportunities for process automation and efficiency.
• Own crew labor, travel, and manning agency budgets; deliver accurate forecasts and proactive cost controls while maintaining service levels that support fleet operations.
• Serve as the primary HR partner to shipboard leadership, providing strategic guidance on crew relations, workforce planning, and complex employee matters across the fleet.
• Other duties as assigned.

• Deep, working knowledge of MLC 2006, ILO conventions, flag state requirements, and international maritime labor law; able to apply regulatory frameworks practically in a fast-moving operational environment.
• Demonstrated experience negotiating and administering CBAs, with a track record of building constructive, durable union relationships in a maritime or similarly complex environment.
• Strong background in crew management systems, payroll operations, and workforce planning in a maritime or similarly regulated, operationally complex environment; experience with Adonis and/or Brightwell a plus.
• Exceptional interpersonal and cross-cultural communication skills, with the credibility and presence to engage effectively with crew, union representatives, port agents, and senior leadership alike.
• 7+ years of progressive maritime HR experience, including demonstrated leadership of multi-functional teams spanning fleet planning, crew operations, or crew welfare.

• Familiarity with AI-powered tools (e.g., Copilot, automation platforms, or HR analytics tools) and a curiosity about how emerging technology can improve workforce planning, reporting, and operational efficiency.

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.