Entertainment Director

Department: Entertainment

Employment Type: Fixed Term Contract

Reporting To: Hotel General Manager

Description

The Entertainment Director leads Holland America Line's Entertainment Department onboard the ship, overseeing the Stage Staff, Activities Team, Resident and Guest Performers, and Presenters. They help set the vision for programming across all venues, shape the department’s culture, and ensure the team delivers entertainment with consistency, creativity, and excellence. The Entertainment Director is accountable for developing talent, fostering a motivated and professional team, and serving as the primary connection with shoreside Entertainment Operations.

Working in partnership with the Hotel General Manager and shoreside partners, the Entertainment Director ensures that onboard programming enhances the guest experience and aligns with company standards. This role requires sound judgment, emotional intelligence, and decisive leadership to achieve company goals and create an entertainment program that enriches the guest journey.

Key Job Responsibilities

• Lead the Entertainment Department, including Stage Staff, Activities Team, and performers, fostering professionalism, teamwork, and accountability.
• Guide team development through coaching, feedback, and performance management.
• Maintain a visible presence at select events and guest functions, representing the Entertainment Department and reinforcing brand standards.
• Provide a superior entertainment experience that meets artistic, technical, and operational standards, including World Stage presentations.
• Oversee daily programming and the cruise arc, ensuring the schedule delivers a consistent and engaging guest experience.
• Tour manage Resident and Guest Performers, Presenters, entertainment vendors, and charters, providing clear communication, leadership, and support.
• Manage entertainment inventory, including stock, replenishment, repairs, and storage, to support seamless operations.
• Oversee accommodations for the entertainment team, performers, presenters, and contracted vendors.
• Oversee departmental administration, including scheduling, time and attendance, in-port manning, performance appraisals, document compliance, and joining requirements for performers and presenters.
• Communicate regularly with shoreside partners regarding workforce planning, staffing needs, and departmental updates.
• Ensure compliance with company health, safety, security, and environmental regulations.
• Maintain a professional appearance and set standards for dress and grooming across the department.

Desired Skills

Minimum Experience

• Bachelor’s degree in business, hospitality management, or related field of study, or equivalent professional experience
• Five years of experience in entertainment, hospitality, or guest-facing leadership roles
• Proven experience leading large, diverse teams with accountability for scheduling, administration, and performance management
• Exceptional communication and presentation skills, with the ability to interact confidently with guests, colleagues, and shoreside partners
• Strong organizational skills with proficiency in Microsoft applications including Word, Excel, and Outlook
• Knowledge of compliance requirements related to scheduling, documentation, and shipboard HR processes
• Ability to make sound decisions under pressure and manage multiple priorities within tight deadlines

Preferred Experience

• Prior experience as an Entertainment Director or equivalent senior entertainment leader on a premium or luxury cruise line
• Demonstrated success leading shipboard entertainment departments, including stage staff, activities teams, and performers
• Experience curating and overseeing large-scale productions, signature events, and enrichment programming across multiple venues
• Proven ability to foster professionalism, teamwork, and accountability within a multicultural workforce
• Experience collaborating with Hotel General Managers and shoreside operations to align entertainment delivery with company goals
• Strong track record of delivering guest satisfaction through polished, creative, and well-executed entertainment programming