Court Supervisor Jobs (NOW HIRING)

Montauk Yacht Club
Spanning 16 acres of waterfront expanse, untouched natural beauty, and endless views, Montauk Yacht Club is a resort haven on the calm waters of Lake Montauk—bridging a legacy of East End tradition with Star Island adventure, exceptional dining at Ocean Club Montauk, elevated wellness offerings, and direct access to the Hamptons’ largest marina…all from the team behind Proper Hospitality.
Job Summary:
The Court Supervisor is responsible for overseeing daily court operations while ensuring an exceptional guest experience. This role manages court bookings, supports programming and events, and leads the court team to maintain high standards of service, safety, and organization. The Court Supervisor plays a key role in driving operational efficiency, resolving guest concerns, and ensuring all court facilities are maintained to brand standards. The ideal candidate is a proactive leader with strong organizational skills and a passion for hospitality and recreation.
Essential Job Duties and Responsibilities:
Court Operations & Scheduling:
o Oversee and manage court bookings, including rentals, lessons, and reservations.
o Ensure efficient and professional guest check-in and check-out processes.
o Provide accurate information on services, programs, events, and memberships.
o Supervise scheduling for court time, lessons, and activities to optimize utilization.
o Maintain and regularly update the court and event calendar.
Guest Service & Experience:
o Lead by example in delivering exceptional customer service and hospitality.
o Address and resolve guest concerns or escalations in a timely and professional manner.
o Ensure a welcoming, organized, and high-quality court environment at all times.
o Support guests with equipment, rules, and general inquiries.
Team Leadership & Development:
o Supervise, support, and motivate court staff to ensure high performance and service standards.
o Assist with staff scheduling, shift coverage, and daily task delegation.
o Provide training, coaching, and ongoing feedback to team members.
o Foster a positive, team-oriented work environment.
Retail & Revenue Support:
o Oversee retail and beverage cart operations, ensuring accurate transactions and strong sales performance.
o Support upselling of court programs, lessons, memberships, and retail offerings.
o Monitor inventory levels and assist with ordering and stock management.
Court Maintenance & Operations:
o Ensure courts are clean, safe, and properly set up before and after use.
o Oversee routine maintenance such as net adjustments, court sweeping, and equipment organization.
o Monitor court conditions and ensure any maintenance or safety concerns are reported and addressed promptly.
o Maintain organization and presentation of all court areas, storage spaces, and equipment.
Events & Programming Support:
o Assist in planning, coordinating, and executing court-related events, tournaments, and special programming.
o Ensure events run smoothly, including staffing, setup, and guest experience.
o Collaborate with instructors and event teams to deliver high-quality programming.
Administrative & Operational Support:
o Oversee POS transactions, payments, and daily financial accuracy.
o Ensure proper record-keeping and reporting for court usage and revenue.
o Coordinate with other departments (e.g., Front Desk, Events, Recreation) to support operations.
o Enforce all court rules, policies, and safety procedures.
Health & Safety Compliance:
o Ensure all operations comply with company policies and safety standards.
o Maintain a safe environment for guests and team members at all times.
o Monitor adherence to court rules and proper equipment usage.
Education and/or Experience
• High school diploma or equivalent required.
• Previous experience in recreation, sports facilities, hospitality, or a related field preferred.
• Supervisory or leadership experience preferred.
• Experience with POS systems and scheduling tools is a plus.
Skills/Specialized Knowledge
• Strong leadership and team management skills.
• Excellent communication and guest service abilities.
• Strong organizational and multitasking skills.
• Ability to resolve issues and make decisions in a fast-paced environment.
• Sales-oriented mindset with the ability to drive revenue.
• Attention to detail and operational awareness.
• Knowledge of court sports (e.g., tennis, pickleball) is a plus.
Physical Demands
• Ability to stand and walk for extended periods of time.
• Ability to lift and carry up to 25 pounds (e.g., equipment, supplies).
• Ability to work outdoors in varying weather conditions.
• Flexibility to work evenings, weekends, and holidays as required.
Why Join Proper Hospitality
At Proper, we build experiences that move people — and that begins with the team behind them. As a best-in-class employer, we’re committed to creating one of the Best Places to Work in hospitality by nurturing a culture where creativity, excellence, and humanity thrive together.
Everything we do is grounded in the belief that hospitality is more than a profession - it’s an opportunity to care for others and make lives better. Guided by the Pillars of Proper, we show up with warmth and authenticity (Care Proper), strive for excellence in everything we do (Achieve Proper), think creatively and resourcefully (Imagine Proper), and take pride in the style and culture that make us who we are (Present Proper).
We believe our people are our greatest strength, and we invest deeply in their wellbeing, growth, and sense of belonging. From comprehensive benefits to meaningful development programs, Proper is designed to help you build a career, and a life, that feels as inspiring as the experiences we create for our guests.
Our Commitment: Building the Best Place to Work
Our Best Place to Work initiative is a living commitment — a continuous investment in our people, our culture, and our purpose. We listen, learn, and evolve together to create an environment where everyone feels empowered to imagine boldly, achieve confidently, care deeply, and present themselves authentically.
At Proper, joining the team means more than finding a job — it means joining a community that believes in building beautiful experiences together, for our guests and for one another.
Proper Hospitality is an equal-opportunity employer. We provide employment opportunities to all individuals regardless of race, color, religion, sex, national origin, age, disability, gender identity or expression, genetics, or any other federally or state-protected category.
We also consider qualified applicants with criminal histories in accordance with local Fair Chance Hiring Ordinances.
Equal Opportunity Employer
This employer is required to notify all applicants of their rights pursuant to federal employment laws.
For further information, please review the Know Your Rights notice from the Department of Labor.