Director, Entertainment Operations

Holland America Group•Fort Lauderdale, FL

1d•Hybrid

About The Position

The Director, Entertainment Operations leads the Entertainment Operations vertical and owns the day-to-day delivery of the Princess Cruises entertainment program across the fleet. The role establishes and maintains programming standards, scheduling guidelines, and operational frameworks to support a consistent, intentional, high-quality guest experience on every voyage. It oversees teams responsible for music programming, guest entertainers, enrichment, activities, family programming, and operations, and aligns their work with the Princess Cruises Entertainment Strategy. The Director is the primary shoreside point of accountability for Cruise Director performance and shipboard entertainment execution. The position builds communication, training, and oversight between shoreside teams and the fleet, including through a fleet pod support structure with four traveling Cruise Director support roles. It also directs guest-facing entertainment communication and marketing initiatives, including the Patter, the Princess app, the Princess Entertainment website, pre-cruise communications, and the department’s external brand presence. The role leads direct and indirect reports across multiple programming functions, provides functional oversight of shipboard Cruise Directors, and works cross-functionally with Hotel Operations, Finance, Marketing, Food & Beverage, and other stakeholders. It is accountable for programming and operational budgets and has a direct influence on guest satisfaction, NPS, and the quality and competitive positioning of the Princess Cruises entertainment experience. The position is classified as in-office. Employees work from a designated Princess office Monday through Thursday and may work from home on Fridays. Travel is 25–50%, with shipboard travel likely. Work is primarily in a climate-controlled environment with minimal safety or health hazards. Work beyond normal business hours or on weekends may occasionally be required.

Requirements

Bachelor’s degree in Entertainment Management, Hospitality, Business Administration, or a related field, or equivalent professional experience.
Deep knowledge of cruise ship entertainment programming across live music, guest entertainers, enrichment, activities, gameshows, and theatrical experiences, including how categories interact across a voyage.
Familiarity with shipboard operations, including scheduling systems, the Patter, and the Princess app.
Ability to conduct competitive analysis and benchmarking across the cruise, entertainment, and hospitality industries.
Understanding of workplace policies and procedures and familiarity with team collaboration tools and techniques.
Strong time management and organizational skills.
Exceptional communication and presentation skills, including the ability to translate programming strategy into clear operational guidance for shipboard teams.
Strong analytical capability to review guest satisfaction data, NPS, and programming metrics and draw actionable conclusions.
Ability to manage complex, multi-stakeholder projects and marketing initiatives across department lines.
Ability to collaborate effectively with colleagues, work as part of a team, maintain reliable and consistent attendance, be punctual, meet deadlines, and demonstrate professionalism.
Ability to work beyond normal business hours or on weekends occasionally to support business needs, projects, or operations.

Nice To Haves

Advanced degree or professional development in hospitality management, entertainment programming, or organizational leadership.

Responsibilities

Develop, communicate, and enforce fleet-wide entertainment programming guidelines and scheduling standards.
Establish onboard scheduling principles covering voyage structure, evening flow, venue and space assignments, off-limits guidelines, programming strategy, and family programming; ensure integration with shipboard systems and consistent fleet application.
Drive the quality and artistic integrity of non-theatrical programming, including live music, guest entertainers, enrichment, activities, gameshows, parties, and interactive events.
Shift entertainment scheduling from a volume-driven model to an intentional, guest-curated approach, optimizing event placement and flow and ensuring the Patter and app accurately present the entertainment offer.
Serve as the primary shoreside point of accountability for Cruise Director performance, programming execution, and operational standards.
Establish communication, training, and oversight between shoreside teams and the fleet, including developing a fleet pod support structure with four traveling Cruise Director support roles.
Provide Cruise Directors with guidance and direct support on scheduling decisions, activity execution, guest entertainer management, and enrichment delivery.
Train Cruise Directors and shipboard entertainment teams on programming principles, standards, and product launches.
Oversee music programming and ensure live and background music is curated for the Voyager guest profile and top-performing genres, with genre strategy marketed onboard and pre-cruise.
Set the direction, scope, and standards for the Princess signature Enrichment program, distinguishing it from revenue-generating activities and overseeing its fleet-wide execution across destination programming, port information, cultural content, and interactive discovery.
Oversee guest entertainer and enrichment booking, ensuring quality, consistency, and program management for headline acts, lecturers, comedians, and speakers, and escalating quality or availability issues.
Oversee activities and family programming teams and ensure delivery against departmental objectives, including gameshows, destination trivia, party branding and theming, youth and family programming, and interactive experiences; intervene when standards are not met.
Improve guest entertainment communications, including Patter accuracy and usability, separation of entertainment from revenue content in the app, and onboard signage and marketing.
Lead pre-cruise entertainment marketing, including the Princess Entertainment website, pre-cruise communications, and external-facing messaging, in partnership with Commercial, Marketing, and Communications stakeholders.
Develop and maintain the department’s external brand presence and digital footprint to enhance brand perception and attract entertainment talent.
Promote entertainment throughout the guest journey, from pre-booking through embarkation, the at-sea experience, and post-cruise engagement.
Create key department presentations and support major public appearances, industry events, and stakeholder meetings on behalf of Entertainment Operations.
Manage programming, enrichment, activities, and operations budgets.
Use guest satisfaction data, NPS, and programming metrics to draw actionable conclusions and guide programming decisions.
Conduct competitive analysis and benchmarking across cruise, entertainment, and hospitality industries to inform strategic development.
Manage complex, cross-functional projects and marketing initiatives, and represent the Entertainment function with internal and external stakeholders.