Fleetwide Entertainment & Engagement Manager

Windstar Cruises, LLC.; Miami (FL); On-site; USD 110,000 - 150,000; Full time

Benefits offered by this job

Medical, Dental & Vision

HSA & FSA

Life & Disability

Accident, Hospital & Critical Illness

Pet Insurance

Vacation, Sick Time and paid Holidays

401(k) with Company Match

Employee Assistance Plan

Education Assistance and Employee Dis,

Job summary

Windstar Cruises, LLC. seeks a Manager of Entertainment & Engagement Operations to lead fleetwide programs, talent sourcing, and day-to-day operational management of aboard entertainment and guest experiences.

You will oversee content systems, enrichment partnerships, and shipboard scheduling, ensuring alignment with strategic priorities and guest satisfaction across Windstar’s fleet.

Qualifications

• Bachelor’s degree or equivalent; 5+ years in entertainment management.
• Cruise ship or multi-venue hospitality experience preferred.
• Strong ability to evaluate talent, programming concepts, and guest experiences.

Responsibilities

• Lead fleetwide entertainment and guest engagement programs aligned with strategy and guest experience objectives.
• Source, contract, schedule, and manage entertainment talent and enrichment partners.
• Oversee shipboard entertainment schedules, content updates, and LED wall content creation.
• Manage budgets, vendors, and operational standards for consistent program delivery.
• Provide leadership and development for entertainment teams and onboard staff.

Skills

Entertainment management

Guest programming

Live events

Hospitality entertainment

Vendors management

Talent management

Project management

Communication skills

Education

Bachelor's degree

Tools

Microsoft 365

Contract management

Budgeting

Entertainment content systems

Job description

Windstar Cruises, LLC. seeks a Manager of Entertainment & Engagement Operations to lead fleetwide programs, talent sourcing, and day-to-day operational management of aboard entertainment and guest experiences.

You will oversee content systems, enrichment partnerships, and shipboard scheduling, ensuring alignment with strategic priorities and guest satisfaction across Windstar’s fleet.