Manager of Entertainment Operations

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 Manager, Entertainment & Engagement Operations is responsible for the implementation, administration, and day-to-day operational management of Windstar's fleetwide entertainment, enrichment, and guest engagement programs. The role manages entertainment talent, workforce planning, shipboard entertainment operations, technical requirements, content systems, budgets, vendors, and operational standards to ensure consistent execution of the company's entertainment and engagement strategy across the fleet.

• Entertainment & Engagement Operations
  - Implement, manage, and continuously enhance fleetwide entertainment and engagement programs in alignment with established programming strategy, standards, and guest experience objectives.
• Operationalize approved entertainment concepts, programming frameworks, and seasonal initiatives, and recommend enhancements based on guest feedback and shipboard performance.
• Works with the Senior Manager of Experience Development to execute the entertainment and engagement components of approved Experience Development initiatives.
• Support new voyage and itinerary development by implementing entertainment and enrichment programming aligned with the established guest experience strategy.
• Programming Development & Content Management
  - Manage and continuously develop cultural, local, and destination-focused entertainment and enrichment programs, including local performers, musicians, workshops, lecturers, cultural ambassadors, and regional experts, within the established programming strategy.
• Source, negotiate, coordinate, and manage entertainment talent and enrichment partners in collaboration with local operators, destination partners, and specialized vendors.
• Own the day-to-day sourcing, contracting, scheduling, and administration of local entertainment engagements, with shipboard teams assuming execution responsibility after confirmed handoff.
• Manage enrichment speaker sourcing, scheduling, contracting, and operational coordination in alignment with established enrichment strategy and itinerary requirements.
• Provide guidance and support to shipboard teams in the development and execution of cruise-specific entertainment schedules and programming layouts.
• Oversee content updates and enhancements related to onboard entertainment and engagement within the interactive television and guest information systems.
• Selects and manage on demand content (movies, series, music) on the interactive television.
• Manage the onboard background music and DJ program in partnership with approved music providers.
• Manage the development of new content creation for LED Walls.
• Provide operational support and guidance to shipboard teams to ensure consistent execution of entertainment programs across the fleet.
• Talent Management & Leadership
  - Lead the sourcing, recruitment, interviewing, casting, contracting, onboarding, and performance management processes for Entertainment & Engagement Managers, Entertainment & Engagement Hosts, Entertainment Activities Hosts, musicians and bands, specialty musicians, piano…