Director, Entertainment Experience and Programming

HollandAmerica Line has been exploring the world since 1873. Our ships offer innovative features and enriching experiences focused on destination exploration and personalized travel, inviting guests to savor the journey.

We are looking for a Director of Entertainment Product & Programming. The Director of Entertainment Product & Programming leads Holland America Line and Seabourn’s Entertainment Experience Team, overseeing the strategic development, integration, and continuous evolution of all guest-facing entertainment products. This role supervises and guides the Experience Owners for Shows & Live Music, Activities & Destination Information, Speakers & Cultural Enrichment, and Media & Events — ensuring their work aligns with brand identity, guest demographics, the Entertainment Experience Lifecycle, and the three strategic pillars : Fit & Appeal, Breadth & Frequency, and Trade Adaptation. The Director ensures that every entertainment experience — from world-class mainstage productions to enrichment talks, activities, and onboard media — is designed with clarity, authenticity, cultural intelligence, and operational feasibility. They serve as the principal architect of cross-category entertainment strategy and work closely with Process & System Owners to ensure scalability, quality, and cost discipline across 16 ships. This is a senior strategic role requiring creative judgment, systems thinking, organizational leadership, strong emotional intelligence, and the ability to maintain the taste standard for both HAL and Seabourn brands.

Responsibilities

Leadership and Execution : Directly lead, coach, and develop the Experience Owners (EOs), each reasonable for the overall effectiveness of their assigned area of the entertainment experience : Shows & Live Music, Activities & Destination Information, Speakers & Cultural Enrichment, Media & Events. Ensure cross-category cohesion, shared standards, and unified strategic direction. Drive a culture of clarity, taste, emotional intelligence, and accountability within the Experience Team.

Entertainment Product Development & Road mapping : Lead the multi-year entertainment product development strategy for both brands, in partnership with the VP, Entertainment. Oversee portfolio planning across daily entertainment, signature experiences, long and complex itineraries, and new product initiatives. Ensure all experience roadmaps consider the strategic pillars and brand vision as defined based on guest insights and company goals. Decide what goes into the fleet, why, and when with oversight of end-to-end product development.

Lifecycle Governance — Oversight of Design & Development : Own the Design & Develop stage at the leadership level; ensure each EO executes it with effectiveness and clarity. Coach EOs in experience design, creative direction, and product management, and overall calibration within each brand's distinctive identity and brand standards. Ensure experiences are simple to operate, scalable, and cost efficient for desired impact. Partner with Process & System Owners to ensure each product meets requirements for Casting, Tech / Safety, Procurement, and Delivery / Sustained Quality.

Brand Integrity & Differentiation : Serve as a steward of both HAL and Seabourn entertainment identities. Partner closely with the Marketing and Guest Experience leaders for each brand, to ensure standards are protected and onboard experiences developed and executed in collaboration with other hotel departments for optimal impact. Collaborate with the VP, Entertainment to ensure that all pre and post cruise guest communications are directly correlated with the actual onboard experience, including monitoring each brand's website and sales materials. Uphold brand taste level across all entertainment experiences; eliminate clichés, disingenuity, or off-brand characteristics to confirm all creative and product decisions and executions are data-driven and in service to each brand's primary and emerging audiences.

Strategic Partnerships & Visibility : Collaborate with VP Entertainment, Marketing, and executive leadership on high-profile talent opportunities, brand partnerships, and storytelling that aligns with each brand's direction and goals. Represent the department in cross-functional strategy discussions, providing thought leadership and product vision. Help source, develop, and maintain important business partnerships with casting, talent, and creative agencies for overall cost management, industry competition, and the ongoing continuity and success of the guest experience.

Knowledge & Skills

The Director of Entertainment Product & Programming holds enterprise-wide responsibility for the full entertainment ecosystem across both Holland America Line and Seabourn, shaping every guest-facing entertainment product delivered on 16 ships. This role oversees the strategic development, integration, and continuous evolution of all entertainment categories—Shows & Live Music, Activities & Destination Information, Speakers & Cultural Enrichment, and Media & Events—ensuring each aligns with brand identity, guest demographics, and the Entertainment Experience Lifecycle. As the principal architect of cross-category strategy, the Director defines what experiences enter the fleet, why they matter, and how they scale, balancing creative ambition with operational feasibility, cost discipline, and long-term portfolio planning.

The Director applies systems thinking and creative judgment to solve complex challenges inherent in delivering world-class entertainment at scale. They navigate constraints related to casting, technical requirements, safety, procurement, and shipboard operations, ensuring each product is both innovative and executable. When issues arise—whether related to brand alignment, guest feedback, operational complexity, or cost—the Director leads root cause analysis and drives solutions that balance artistic integrity with business realities. Their ability to anticipate risks, eliminate off-brand elements, and refine experiences through data-driven decision-making ensures that both brands maintain a competitive edge and deliver entertainment that consistently exceeds guest expectations.

The Director’s decisions directly influence guest satisfaction, brand differentiation, and the commercial performance of both cruise lines. By upholding the strategic pillars of Fit & Appeal, Breadth & Frequency, and Trade Adaptation, the Director ensures that entertainment offerings resonate with core and emerging audiences while supporting itinerary design, marketing narratives, and onboard revenue opportunities. Their work safeguards the taste standard for both brands, ensuring every production, enrichment program, and media touchpoint reflects clarity, authenticity, and cultural intelligence. Through strong governance and cross-functional alignment, the Director elevates the consistency, quality, and relevance of the entertainment experience fleetwide.

This role provides senior-level leadership to the Experience Owners, coaching them in creative direction, product management, and brand stewardship while fostering a culture grounded in clarity, emotional intelligence, and accountability. The Director ensures cohesion across categories, unifying standards and guiding the team toward a shared strategic vision. They partner closely with Marketing, Guest Experience, and Process & System Owners to ensure entertainment products are not only compelling but also operationally sound, scalable, and aligned with broader company goals. As a visible leader, the Director represents the department in cross-functional forums and collaborates with executive leadership on high-profile partnerships and talent opportunities.

Requirements

Bachelor's and / or Master's Degree (preferred, not required) in a related field : Performing Arts, Film / Creative Production, Technical Theatre, Business Administration, Marketing, etc. Demonstrated excellence in written and verbal communication, leadership, critical thinking, problem-solving, organization, and time management.

Proficiency using Microsoft Outlook, Excel, Word, Powerpoint and other Project / Product Management platforms (preferred) like Airtable, Asana, etc.

Demonstrated familiarity with AI-assisted tools (e.g., ChatGPT, CoPilot, Airtable AI, or similar) and ability to incorporate them into creative development, analysis, or project management.

7+ years in entertainment leadership roles managing creative, experiential, or product teams.

3–5 years of corporate entertainment leadership (cruise or similar scale).

Preferably shipboard experience to understand onboard operational realities.

2+ years of demonstrated experience with an ultra-luxury hospitality brand.

Demonstrated experience overseeing multiple entertainment categories or disciplines.

Experience developing strategic roadmaps and guiding multiple product owners, managing end-to-end product development.

Travel

25-50% with shipboard travel likely

Work Conditions

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

Physical Demands

Must be able to remain in a stationary position at a desk and / or computer for extended periods of time.

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

Holland 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
• Base Salary Range : $120,000 to $162,000. The range is applicable for the labor market where the role is intended to be hired. Final base salary is directly related to each candidate's qualifications and experience uniquely.

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 : https : / / www.hollandamerica.com / en_US / our-company / mission-values.html

Holland America 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)

Holland America will provide reasonable accommodations 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 recruiting@hollandamericagroup.com

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