Activities Supervisor

Highgate is a leading real estate investment and hospitality management company with over $15 billion of assets under management and a global portfolio of more than 400 hotels spanning North America, Europe, the Caribbean, and Latin America. With a 30-year track record as an innovator in the hospitality industry, this forward-thinking company provides expert guidance through all stages of the property cycle, from planning and development through recapitalization or disposition. Highgate continues to demonstrate success in developing a diverse portfolio of bespoke lifestyle hotel brands, legacy brands, and independent hotels and resorts, featuring contemporary programming and digital acumen. The company utilizes industry-leading revenue management tools that efficiently identify and predict evolving market dynamics to drive outperformance and maximize asset value. With an executive team of seasoned hospitality leaders and corporate offices worldwide, Highgate is a trusted partner for top ownership groups and major hotel brands. www.highgate.com

Discover more sun and more fun! Escape to a tropical beachfront paradise complete with everything you need for the perfect getaway, including delicious dining, beachfront bars, relaxing comforts, and endless activities. Here you’ll stay at one, play at two — with two connecting resorts right on the soft white sands of St. Pete Beach. Whether you’re looking for family fun, a romantic retreat, a group getaway, or anything in between, it’s all here at TradeWinds Island Resorts. https://www.tradewindsresort.com/careers

Follow your passion all the way to paradise at TradeWinds Resort! Located along the gorgeous Gulf Coast on St. Pete Beach, a Top-Ranked U.S. Beach, TradeWinds features two destination resorts just 200 flip-flops from one another. 

We’re proud to share that our management company, Highgate, has been recognized as a 2026 USA TODAY Top Workplaces award winner. When you join the TradeWinds team, you become part of a culture that values passion, collaboration, excellence, purpose, and inclusivity. If you’re passionate about creating memorable experiences and making a meaningful impact, we’d love to meet you. Bring your passion to paradise and discover where your career can take you at TradeWinds! 

The Activities Supervisor is responsible for planning, coordinating, and executing engaging recreational events and group experiences that enhance the overall guest experience for our "Campers" ages 5-17. This role oversees holiday events, themed activations, birthday parties, and youth programs while supervising frontline staff, vendors, and event logistics. The Supervisor ensures all programs are safe, well-organized, on-brand, and delivered with exceptional service standards and most importantly, FUN!

Program Development

• →

  Develop, plan, and implement engaging, creative, and age-appropriate recreational programs primarily for children and teens ages 5–17.

• →

  Coordinate and lead a variety of resort activities, including poolside events, beach games, arts and crafts, interactive experiences, and seasonal programming.

• →

  Create memorable experiences that encourage guest participation, family engagement, and repeat visitation.

• →

  Continuously introduce fresh ideas and activities that enhance the overall resort experience.

• →

  Ensure activities are properly organized, prepared, and executed according to established schedules.

Staff Management

• →

  Supervise, train, coach, and motivate recreation team members to deliver exceptional guest experiences.

• →

  Assist with staff scheduling, daily assignments, and ensuring appropriate staffing levels for scheduled activities.

• →

  Ensure team members understand and consistently follow departmental Standard Operating Procedures (SOPs).

• →

  Lead by example by maintaining a positive, energetic, approachable, and guest-focused attitude.

• →

  Provide ongoing feedback and support to encourage employee development and accountability.

Guest Engagement

• →

  Create a welcoming and energetic environment that encourages guests of all ages to participate in resort activities.

• →

  Interact with guests and families to understand their interests, preferences, and expectations.

• →

  Promote daily activities and encourage guest participation throughout the resort.

• →

  Address guest questions, concerns, and feedback professionally and promptly.

• →

  Monitor guest satisfaction and use feedback to continuously improve programming and experiences.

Safety and Compliance

• →

  Conduct routine inspections of activity areas, equipment, and facilities to identify and address potential safety concerns.

• →

  Ensure team members are properly trained on safety procedures, emergency response protocols, and age-appropriate supervision.

• →

  Immediately report accidents, incidents, and safety concerns to the appropriate leadership team.

Equipment and Facility Management

• →

  Oversee the organization, cleanliness, maintenance, and proper storage of recreational equipment and supplies.

• →

  Ensure activity spaces, poolside areas, and beach recreation areas are clean, organized, and guest-ready.

• Education: Bachelor's degree in Recreation Management or related field. (preferred, not required) 
• Experience: in resort recreational youth program management or related field.
• Lifeguard Certification - TradeWinds will provide training.
• Skills: Leadership, communication, guest service. 
• Creativity: Innovative thinking for engaging activities.
• Customer Service: Commitment to exceptional guest satisfaction.
• Dependable and dedicated work ethic. 
• Must be comfortable working outdoors for 8 hours or more in Florida’s hot climate.

This job opening was posted on November 12, 2026 and will remain open for at least 75 days.