Manager of Entertainment 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.

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.

Responsibilities

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 entertainers, Polynesian Ambassadors, and other entertainment personnel.

• Manage workforce planning and rotation schedules for onboard entertainment positions.

• Maintain and update entertainment job  descriptions, role expectations, and operating resources in partnership with the Senior Manager as programming and fleet requirements evolve.

• Provide leadership, coaching, and support to shipboard entertainment teams to ensure consistent program delivery and operational excellence.

• Directly supervise the Corporate AV Manager and provide operational direction, performance support, and alignment with fleetwide entertainment requirements.

Technical Operations & Equipment Management

• Oversee the operation, functionality, design, and long-term planning of shipboard entertainment and audiovisual systems.

• Partner with shipboard and shoreside teams to identify equipment needs, manage upgrades, and enhance technical capabilities across the fleet.

• Manage the procurement, inventory, and lifecycle of entertainment-related materials and equipment, including audiovisual assets, books, games, prizes, props, and specialty supplies.

• Support shipboard teams in resolving entertainment-related operational and technical challenges.

Entertainment Standards, SOPs & Governance

• Develop and maintain entertainment SOPs, standards, guidelines, and operational resources.

• Implement, maintain, and reinforce approved standards for programming, enrichment, live music, events, and guest activities.

• Identify opportunities for standardization and continuously update documentation to support operational consistency and product evolution.

Financial Management & Administration

• Manage and monitor the approved Entertainment Department operating budget throughout the fiscal year.

• Support annual operating and capital budget development by preparing forecasts, cost requirements, and operational recommendations for entertainment operations.

• Review, code, approve, and monitor entertainment-related invoices, expenses, and departmental spending within established company authority to ensure accuracy and budget compliance.

• Identify opportunities for cost optimization while maintaining program quality and guest satisfaction.

Compliance, Safety & Operational Support

• Ensure all entertainment operations are conducted in compliance with company policies, SEMS requirements, and applicable maritime, regulatory, and safety standards.

• Promote and maintain safe operating practices for shipboard entertainment activities, performers, and technical operations.

Other

• Perform additional projects, assignments, and responsibilities as required in support of departmental and organizational objectives.

Qualifications

• Bachelor's degree or an equivalent combination of education and experience, with a minimum of five years of progressively responsible experience in entertainment management, guest programming, live events, hospitality entertainment, or a related field. Cruise ship or multi-venue hospitality experience is strongly preferred.

• Demonstrated creative ability in entertainment and guest-experience development, including the ability to conceptualize, develop, evaluate, and implement original entertainment, enrichment, and engagement programming aligned with brand identity, guest demographics, destinations, and operational realities.

• Strong creative judgment and entertainment-industry awareness, with the ability to evaluate talent, programming concepts, content, and guest experiences for quality, originality, brand alignment, audience appeal, and operational feasibility.

• Working knowledge of entertainment technology and venue-based audiovisual systems, with sufficient technical understanding to evaluate capabilities, identify operational requirements, support technical teams, and incorporate technology into entertainment and guest-experience development.

• Demonstrated experience managing entertainment talent, including sourcing, auditioning or interviewing, contracting, onboarding, scheduling, coaching, and performance management.

• Proven experience managing vendors, negotiating service agreements, and administering contracts, invoices, and operating budgets.

• Experience developing and implementing SOPs, operating standards, training materials, and quality-assurance processes across multiple locations or vessels.

• Strong workforce-planning and scheduling skills, including the ability to manage rotations, staffing gaps, seasonal demand, and last-minute operational changes.

• Excellent project-management, organizational, and analytical skills, with the ability to manage multiple priorities, deadlines, and stakeholders in a fast-paced environment.

• Strong written, verbal, presentation, negotiation, and relationship-management skills, with the ability to influence shipboard and shoreside partners without direct authority.

• Proficiency with Microsoft 365 applications; experience with scheduling, contract-management, procurement, budgeting, or entertainment content systems is preferred.

• Ability to work flexible hours as operationally required, including evenings, weekends, holidays, and periods aboard vessels; must be able to obtain and maintain required travel documents for international travel.

Travel: This role requires extensive global travel across the Windstar fleet, representing approximately 20% to 25% of annual work time, to oversee entertainment operations, support shipboard teams, and ensure the consistent delivery of exceptional guest experiences

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.