Our Property:

Captiva Island has been the destination of choice for generations of families. South Seas, for many, is where the destination has come to life. The 330-acre retreat and wildlife nature preserve on the Florida Gulf Coast offers elevated coastal experiences and world-class amenities designed to appeal to a multitude of guests. Join this passionate and hardworking team and enjoy working in paradise.

Our Core Values:

We are in the business of creating an authentic sense of place for families to return to time and time again while committing ourselves to creating memorable and fun experiencers through passionate, attentive service. This mantra is reflected in everything we do and every interaction we have whether it be in hospitality operations management, asset management, development, or sales & marketing. Our values define who we are.

• Be Authentic
• Practice Humility
• Cultivate Teamwork
• Value Time
• Be Trustworthy

We offer a very competitive salary and generous benefits including:

• Medical, Dental, Vision Plans
• Paid Life Insurance
• Short- and Long-Term Disability
• Paid Time Off & Holidays
• 401(k) with 100% match up to 4%
• Commuter and Company-paid Toll Programs

Position Overview

The Recreation Supervisor is responsible to assist in overseeing the daily operations of Captiva Landing. This supervisor role ensures that all recreational spaces are maintained to the highest standards while delivering exceptional guest experiences in assistance to the Recreation Manager. The Captiva Landing Recreation Supervisor will provide direction to the team, coordinate daily activities, and ensure compliance with all safety policies and operational procedures. This role is perfect for a passionate and service-driven leader who thrives in a dynamic, guest-facing environment.

Key Responsibilities

Leadership & Team Management

• Supervise, train, and mentor a team of recreation attendants, ensuring excellent guest service and adherence to resort policies.
• Provide ongoing role-playing scenarios to enhance team members’ communication, problem-solving, and service skills.
• Lead pre-shift meetings to communicate goals, updates, and expectations for the day.
• Foster a positive and professional work environment that encourages teamwork, accountability, and high performance.
• Assist with hiring, onboarding, and evaluating team members to ensure alignment with resort standards.
• Assist with administrative duties like scheduling, ordering and monthly planning.

Pool & Water Amenity Operations

• Oversee and assist with the setup and breakdown of all pool and water amenity equipment, including lounge chairs, umbrellas, and cabanas.
• Ensure furniture layout is organized, aesthetically pleasing, and aligned with resort standards.
• Ensure that all recreational areas are clean, well-maintained, and properly stocked with towels, and essentials.
• Monitor pool capacity, adjusting setups as needed for guest comfort and safety.
• Enforce resort rules and safety regulations, addressing guest inquiries and concerns in a professional manner.
• Coordinate VIP setups.

Guest Experience & Cabana Rentals

• Actively engage with guests to enhance their experience, respond to feedback, and resolve any concerns promptly.
• Maintain high visibility on the pool deck, assisting guests as needed and ensuring exceptional service.
• Manage cabana reservations and coordinate guest check-in/check-out for rentals.
• Provide personalized service to cabana guests, including towel delivery, amenities, and special requests.
• Respond promptly to guest inquiries and resolve concerns with professionalism and care.

Water Slide & Amenity Safety

• Oversee water slide operations, ensuring all safety protocols are followed.
• Train and supervise staff on resort emergency response procedures.
• Conduct regular inspections of water features and slides for safety and functionality.

Equipment Maintenance

• Perform routine checks and minor maintenance on poolside furniture.
• Report and coordinate repairs with the maintenance team as needed.
• Maintain inventory of pool supplies and request replenishments when necessary.

Operational Excellence & Compliance

• Uphold all safety standards, emergency procedures, and risk management protocols in recreational areas.
• Conduct regular inspections of pool and water amenity equipment, ensuring proper maintenance and cleanliness.
• Maintain detailed records of daily operations, including guest participation, incidents, and equipment usage.
• Work closely with other departments alongside Recreation Manager, such as housekeeping, security, and guest services, to ensure seamless resort operations.
• Assist with seeking opportunities to enhance recreational offerings and elevate the guest experience.

Qualifications & Skills

• Prior experience in recreation, hospitality, or resort management preferred.
• Strong leadership skills with the ability to motivate a team.
• Excellent communication and guest service skills.
• Knowledge of water safety and pool operations.
• Ability to work outdoors in various weather conditions.
• CPR and First Aid certification (or willingness to obtain).

Pay Rate: $25/hr, Full-time

Schedule: Flexible, may include weekend shifts

Start Date: November 2025

Timbers Company is a developer and operator of exceptional boutique hotels, residence clubs and resort communities located in some of the most sought-after destinations in the world. We are passionate about creating remarkable experiences with world-class hospitality while exposing our Owners and guests to the humble authenticity of every location that we call home.

Our company (“Company”) fully subscribes to the principles of Equal Employment Opportunity. It is our policy to provide employment, compensation, and other benefits related to employment based on qualifications, without regard to race, color, religion, national origin, age, sex, veteran status, genetic information, disability, or any other basis prohibited by federal, state or local law. 

In compliance with the Americans with Disabilities Act (ADA) and applicable federal, state and/or local laws, it is our policy to provide reasonable accommodation upon request during the application process to applicants in order that they may be given a full and fair opportunity to be considered for employment. As an Equal Opportunity Employer, we intend to comply fully with applicable federal, state and/or local employment laws and the information requested on this application will only be used for purposes consistent with those laws. To the extent required by applicable law, The Company maintains a drug- free workplace.