Manager of Entertainment Operations

Windstar Cruises•Miami, FL

18d

About The Position

The Manager, Entertainment & Engagement Operations is responsible for implementing, administering, and managing Windstar’s fleetwide entertainment, enrichment, and guest engagement programs. The role oversees entertainment talent, workforce planning, shipboard operations, technical requirements, content systems, budgets, vendors, and operating standards to support consistent delivery of the company’s entertainment and engagement strategy across the fleet. The position operationalizes approved programming concepts and seasonal initiatives, develops cultural and destination-focused programming, sources and manages talent and enrichment partners, and supports shipboard teams in executing voyage-specific schedules. It also oversees onboard entertainment content, background music, DJ programming, and new LED-wall content. The manager leads recruitment and performance processes for shipboard entertainment personnel, manages staffing rotations, and directly supervises the Corporate AV Manager. The role oversees audiovisual systems and equipment, develops and maintains operating standards and SOPs, manages departmental budgets and expenses, and ensures compliance with company, maritime, regulatory, and safety requirements. The role requires extensive global travel across the Windstar fleet, approximately 20% to 25% of annual work time, and flexibility to work evenings, weekends, holidays, and periods aboard vessels. Applicants must be able to obtain and maintain required international travel documents.

Requirements

Bachelor’s degree or an equivalent combination of education and experience.
At least five years of progressively responsible experience in entertainment management, guest programming, live events, hospitality entertainment, or a related field.
Demonstrated creative ability in entertainment and guest-experience development, including conceptualizing, developing, evaluating, and implementing original programming aligned with brand identity, guest demographics, destinations, and operational realities.
Strong creative judgment and entertainment-industry awareness, including evaluating 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 sufficient to evaluate capabilities, identify operational requirements, support technical teams, and incorporate technology into programming.
Experience managing entertainment talent, including sourcing, auditioning or interviewing, contracting, onboarding, scheduling, coaching, and performance management.
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 management of rotations, staffing gaps, seasonal demand, and last-minute operational changes.
Strong 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, including the ability to influence shipboard and shoreside partners without direct authority.
Proficiency with Microsoft 365 applications.
Ability to work flexible hours as operationally required, including evenings, weekends, holidays, and periods aboard vessels.
Ability to obtain and maintain required travel documents for international travel.
Ability to travel extensively across the Windstar fleet, approximately 20% to 25% of annual work time.

Nice To Haves

Cruise ship or multi-venue hospitality experience is strongly preferred.
Experience with scheduling, contract-management, procurement, budgeting, or entertainment content systems is preferred.

Responsibilities

Implement, manage, and improve fleetwide entertainment and engagement programs in alignment with established strategy, standards, and guest experience objectives.
Operationalize approved entertainment concepts, programming frameworks, and seasonal initiatives; recommend enhancements based on guest feedback and shipboard performance.
Work with the Senior Manager of Experience Development to execute entertainment and engagement components of approved initiatives.
Support voyage and itinerary development by implementing entertainment and enrichment programming aligned with the established guest experience strategy.
Develop cultural, local, and destination-focused entertainment and enrichment programs, including performers, musicians, workshops, lecturers, cultural ambassadors, and regional experts.
Source, negotiate, coordinate, and manage entertainment talent and enrichment partners with local operators, destination partners, and vendors.
Source, contract, schedule, and administer local entertainment engagements, handing confirmed engagements to shipboard teams for execution.
Manage enrichment speaker sourcing, scheduling, contracting, and operational coordination.
Guide shipboard teams in developing and executing cruise-specific entertainment schedules and programming layouts.
Oversee onboard entertainment and engagement content updates in interactive television and guest information systems.
Select and manage on-demand television content, including movies, series, and music.
Manage onboard background music and DJ programming with approved music providers.
Manage development of new content for LED walls.
Support shipboard teams in consistent execution of fleetwide entertainment programs.
Lead sourcing, recruitment, interviewing, casting, contracting, onboarding, and performance management for shipboard entertainment personnel and performers.
Manage workforce planning and rotation schedules for onboard entertainment positions.
Maintain entertainment job descriptions, role expectations, and operating resources with the Senior Manager.
Lead, coach, and support shipboard entertainment teams.
Directly supervise the Corporate AV Manager and provide operational direction and performance support.
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 improve technical capabilities.
Manage procurement, inventory, and lifecycle of entertainment materials and equipment, including audiovisual assets, books, games, prizes, props, and specialty supplies.
Help shipboard teams resolve entertainment-related operational and technical challenges.
Develop and maintain entertainment SOPs, standards, guidelines, and operating resources.
Implement and reinforce standards for programming, enrichment, live music, events, and guest activities.
Identify standardization opportunities and update documentation to support operational consistency and product evolution.
Manage and monitor the approved Entertainment Department operating budget.
Support annual operating and capital budget development through forecasts, cost requirements, and operational recommendations.
Review, code, approve, and monitor entertainment invoices, expenses, and departmental spending within company authority.
Identify cost-optimization opportunities while maintaining program quality and guest satisfaction.
Ensure entertainment operations comply with company policies, SEMS requirements, and applicable maritime, regulatory, and safety standards.
Promote safe operating practices for shipboard entertainment activities, performers, and technical operations.
Perform additional projects, assignments, and responsibilities in support of departmental and organizational objectives.