Director of Entertainment and Guest Experiences

Create the moments people talk about long after checkout.

We are conducting a confidential search for a Director level leader who lives at the intersection of entertainment, guest experience, and revenue creation. This role is for someone who does not just schedule activities, but curates energy, builds emotional connection, and turns programming into a reason guests return again and again.

You will own the full vision and execution of entertainment, activities, and events, leading a team that brings fun to life daily while ensuring every program aligns with brand standards, guest expectations, and financial performance. This role reports directly to the General Manager and plays a visible, high impact role across the operation.

What You Will Own

Entertainment and Programming

• Design, schedule, and execute a full calendar of entertainment across the property

• Source, book, and manage live entertainment including bands, DJs, specialty acts, and performers

• Oversee contracts, performance quality, logistics, and budgets for all entertainment partners

• Ensure every program feels intentional, polished, and aligned with brand identity

• Stay ahead of entertainment and experiential trends to keep programming fresh and relevant

Team Leadership and Culture

• Lead, coach, and develop a recreation and activities team that delivers high energy experiences

• Oversee supervisors responsible for daily activities, themed programming, poolside events, crafts, and family focused experiences

• Set clear expectations for quality, safety, timing, and guest engagement

• Use feedback and performance insight to evolve programming and elevate team execution

Events and Revenue Creation

• Concept, plan, and execute both signature and recurring events that drive engagement and incremental revenue

• Own all event logistics including staffing, setup, breakdown, vendors, décor, and equipment

• Manage budgets, expenses, and invoicing tied to entertainment and events

• Build events with purpose that support both guest satisfaction and financial goals

Performance and Accountability

• Develop strategies that grow participation, revenue, and guest satisfaction through programming

• Track performance metrics and guest feedback to optimize offerings

• Partner with marketing to promote events and experiences effectively

• Ensure programs stay within budget while delivering strong ROI

Guest Experience and Brand Presence

• Be visible and engaged with guests during events and peak activity periods

• Actively gather guest insight and adjust programming in real time when needed

• Set the tone for hospitality, fun, and high energy throughout the operation

• Ensure the experience feels consistent, memorable, and elevated across all touchpoints

What We Are Looking For

Required

• Three or more years of experience in entertainment management, event leadership, or hospitality programming

• Two or more years leading teams in a high energy, guest facing environment

• Strong scheduling, production, and operational planning skills

• Proven ability to manage budgets and build revenue through experiences

• Confident communicator who leads from the front

• Flexible schedule mindset including evenings, weekends, and holidays

Preferred

• Experience in a resort or high volume hospitality environment

• Background booking live entertainment and managing vendor relationships

• Comfort with event technology, scheduling platforms, and team development

• CPR or First Aid certification or willingness to obtain

Why This Role Is Different

This is not a back of house programming role. It is a visible leadership position with creative influence, ownership, and real impact on the guest journey and bottom line. If you thrive on energy, creativity, and building experiences that matter, this role offers the platform to do just that.