Director, Entertainment Operations

One of the best-known names in cruising, Princess is the world’s leading international premium cruise line and tour company, carrying millions of guests each year to hundreds of destinations around the globe. We give our guests the Medallion Class experience others simply can’t. The Love Boat promises something for everyone.

The Director, Entertainment Operations leads the Entertainment Operations vertical and is the executive owner of the day-to-day delivery of the Princess Cruises entertainment program across the fleet. This is a newly defined role within the restructured shoreside organization, created to bring clear accountability to the quality, consistency, and integrity of the entertainment product as it is experienced by guests on every voyage.

The Director, Operations owns the programming standards, scheduling guidelines, and operational frameworks that govern how entertainment is delivered across all Princess Cruises vessels. This role provides direct oversight of a diverse team covering music programming, guest entertainers, enrichment, activities and family programming. All aligned to the strategic pillars of the PCL Entertainment Strategy.

A key mandate of this role is to build and strengthen the conduit between the shoreside organization and the fleet ensuring Cruise Directors and shipboard teams receive the support, guidelines, oversight, and communication they need to execute the entertainment program at the level the strategy demands.

Here’s a summary of what Princess is looking for in a Director, Entertainment Operations. Is this you?

Responsibilities:

Programming Standards, Scheduling & Guest Experience Integrity

• Own the development, communication, and enforcement of fleet-wide entertainment programming guidelines and scheduling standards, ensuring consistent, intentional placement of events, activities, music, and enrichment across the voyage.

• Establish and maintain the guiding principles for onboard scheduling. Including voyage structure, evening flow, venue and space assignment, off-limits guidelines, programming strategy, and family programming considerations. Ensure these are integrated into shipboard systems and consistently applied across the fleet.

• Drive the quality and artistic integrity of the entertainment program across all non-theatrical programming categories: live music, guest entertainers, enrichment, activities, gameshows, parties, and interactive events.

• Champion the strategic shift in entertainment scheduling from a volume-driven model to an intentional, guest-curated programming approach. Ensuring events are placed where they enhance atmosphere, flow is optimized, and the Patter and app accurately reflect a compelling entertainment offer.

Fleet Support, Cruise Director Oversight & Shipboard Engagement

• Serve as the primary shoreside point of accountability for Cruise Director performance, programming execution, and operational standards, establishing a clear line of communication, training, and oversight between the shoreside team and the fleet.

• Develop and implement the fleet pod support structure, including four traveling Cruise Director support roles, to provide active, ongoing shoreside engagement with shipboard entertainment operations.

• Provide programming guidance and direct support to Cruise Directors on scheduling decisions, activity execution, guest entertainer management, and enrichment delivery.

• Ensure Cruise Directors and shipboard entertainment teams are trained on new programming principles, standards, and product launches.

Music, Enrichment, Activities & Guest Entertainer Program Oversight

• Provide strategic oversight of the music programming function, ensuring the team responsible for live and background music curates a fleet-wide mix intentionally aligned to the Voyager guest profile and top-performing genres, and that genre strategy is actively marketed both onboard and pre-cruise.

• Set the strategic direction for the Princess signature Enrichment program, establishing its scope, standards, and separation from revenue-generating activities, and oversee the team responsible for its development and fleet-wide execution, ensuring it meaningfully encompasses destination programming, port information, cultural content, and interactive discovery across all trades.

• Oversee the guest entertainers and enrichment booking function, holding the team accountable for the quality, consistency, and program management of headline acts, lecturers, comedians, and enrichment speakers across the fleet, and escalating where quality or availability standards are not being met.

• Provide oversight of the activities and family programming teams, ensuring they are delivering against the strategic objectives of the department, including the evolution of gameshows, destination trivia, party branding and theming, youth and family programming, and next-generation interactive experiences, and intervening to course-correct where programming falls short of established standards.

Guest Communication, Brand Presence & Pre-Cruise Marketing

• Drive the strategic initiative to elevate guest communication around entertainment, improving Patter accuracy and usability, separating entertainment content from revenue content in the app, and amplifying onboard signage and marketing for entertainment programming.

• Lead the launch and ongoing management of pre-cruise entertainment marketing, including the Princess Entertainment website, pre-cruise communications, and external-facing entertainment messaging, in partnership with Commercial, Marketing, and Communications stakeholders.

• Develop and maintain the department's external brand presence, including the Princess Entertainment digital footprint, to enhance brand perception and attract high-caliber entertainment talent.

• Ensure entertainment is effectively promoted and visible throughout the guest journey, from pre-booking through embarkation, at-sea experience, and post-cruise engagement.

• Lead the creation of key department presentations and support the execution of major public appearances, industry events, and stakeholder meetings on behalf of the Entertainment Operations vertical.

Knowledge & Skills:

• Scope: This role has the broadest operational scope within the Entertainment department, directly influencing the day-to-day guest experience on every Princess Cruises voyage across the entire fleet. The Director, Entertainment Operations oversees a team of 14 across music programming, guest entertainers, enrichment, activities, family programming, and operations, and maintains active fleet engagement through the Cruise Director oversight structure. This role interfaces regularly with the VP, Entertainment, the two other Director-level peers and cross-functional leaders in Hotel Operations, Finance, Marketing, and Food & Beverage.

• Problem solving: This role routinely manages ambiguous, guest-facing challenges with fleet-wide implications: a scheduling conflict that places competing high-demand events at the same time on the same ship; a booking shortfall in the guest entertainer roster for an upcoming trade; a Cruise Director executing programming in a manner inconsistent with the new guiding principles; or a new interactive event concept that must be adapted for different ship classes and itinerary types. Solutions require both strategic thinking about the entertainment product and practical operational problem-solving in a live hospitality environment.

• Impact: The Director, Entertainment Operations has direct and visible impact on guest satisfaction scores, NPS, and the overall quality of the Princess Cruises entertainment experience. The programming standards and oversight frameworks established in this role determine the baseline quality of entertainment delivery across hundreds of voyages per year. Beyond guest-facing impact, this role shapes Princess Cruises' competitive positioning in the entertainment category and contributes directly to the company's ability to attract and retain guests.

• Leadership: This role leads a team of direct and indirect reports spanning Senior Managers, Managers, and Specialists across four programming functions (music, guest entertainers/enrichment, activities/family, and programming operations). The Director also provides functional oversight of shipboard Cruise Directors and manages the new fleet pod support structure. Cross-functional leadership is required to drive the guest communication and pre-cruise marketing agenda, which spans multiple departments beyond Entertainment. Budget management spans programming, enrichment, activities, and operations functions within the Entertainment Operations vertical.

For all roles:

Knowledge: Understanding of workplace policies and procedures / Familiarity with team collaboration tools and techniques.

Skills: Strong time management and organizational skills

Abilities: Ability to maintain reliable and consistent attendance / Capacity to be punctual and meet deadlines / Ability to collaborate effectively with colleagues and work as part of a team / Demonstrated professionalism in all interactions and tasks.

Essential/Minimum Qualifications:

Education:

• Bachelor's degree in Entertainment Management, Hospitality, Business Administration, or a related field; or equivalent professional experience.

Education (Preferred)

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

• Deep knowledge of cruise ship entertainment programming across multiple categories, including live music, guest entertainers, enrichment, activities, gameshows, and theatrical experiences, with understanding of how these categories interact across a voyage arc. Familiarity with shipboard operations, including scheduling systems, Patter, and the Princess app.

• Ability to conduct competitive analysis and benchmarking across the cruise, entertainment, and hospitality industries to inform strategic development. Understanding of workplace policies and procedures and team collaboration tools and techniques.

• Strong time management and organizational skills.

• Exceptional communication and presentation skills, with 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.

Essential experience required:

• Minimum of 10 years of experience in entertainment operations, programming management, or entertainment production, with demonstrated accountability for the quality and consistency of a live entertainment product across multiple venues or vessels.

• Proven experience managing a multi-functional team across programming, talent booking, and operational disciplines, with experience building and developing direct reports at the Manager and Senior Manager levels.

• Demonstrated experience developing programming standards, scheduling guidelines, or operational frameworks for a live entertainment environment, and successfully implementing those standards across a team or fleet.

• Substantive experience in cruise line entertainment operations, including deep understanding of shipboard programming workflows, Cruise Director operations, and fleet-wide communication and oversight structures.

• Demonstrated ability to conduct ongoing competitive analysis and strategic benchmarking across the entertainment and cruise industries, and to translate findings into actionable programming decisions.

• Experience engaging with and influencing marketing, comm, or communications functions to promote an entertainment product or experience, including digital and pre-cruise channels.

Preferred Experience

• Experience with enrichment program development, destination programming, or travel guide-style content in a cruise or travel context.

• Experience managing interactive entertainment formats including gameshows, trivia, themed parties, or upcharge experiential events.

• Working knowledge of the Princess Cruises fleet, itinerary portfolio, and guest demographics.

Travel: 25-50% with shipboard travel likely

Work Conditions: Work primarily in a climate-controlled environment with minimal safety/health hazard potential.

Physical Demands:. Work beyond normal business hours or on weekends may be required occasionally to support business needs, projects, or operations.

** This position is classified as “in-office.” As an in-office role, it requires employees to work from a designated Princess office Monday through Thursday each week. Employees may work from their homes on Fridays.

Princess provides comprehensive and innovative benefits to meet your needs, including:

What You Can Expect

• Cruise and Travel Privileges for You and Your Family
• Health Benefits
• 401(k)
• Employee Stock Purchase Plan
• Training & Professional Development
• Tuition & Professional Certification Reimbursement
• Rewards & Incentives

Our Culture… Stronger Together

Our highest responsibility and top priority is compliance, environmental protection and the health, safety and well-being of our guests, the people in the communities we touch and serve, and our shipboard and shoreside employees.  Please visit our site to learn more about our Culture Essentials, Corporate Vision Statement and our Core Values at: princess.com/en-us/company-information

Princess is an equal-opportunity employer. All qualified applicants will receive consideration for employment without regard to age, ancestry, color, family or medical care leave, gender identity or expression, genetic information, marital status, medical condition, national origin, physical or mental disability, political affiliation, protected veteran status, race, religion, sex (including pregnancy), sexual orientation, or any other characteristic protected by applicable laws, regulations and ordinances.

Americans with Disabilities Act (ADA)

Princess will provide reasonable accommodation with the application process, upon your request, as required to comply with applicable laws.  If you have a disability and require assistance in this application process, please contact careers@carnival.com.

#PCL

#LI-Hybrid

#LI-TM1