Retail Supervisor

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 Retail Supervisor is responsible for overseeing daily retail operations while delivering an exceptional guest experience. This role leads and supports the retail team, ensures accurate transaction processing, drives sales performance, and maintains a clean, organized, and visually appealing retail environment. The ideal candidate is a proactive leader who is detail-oriented, service-driven, and committed to creating a seamless and engaging shopping experience for all guests.

Essential Job Duties and Responsibilities:

• Guest Service & Sales Leadership:

o Lead by example in providing warm, professional, and engaging guest service, creating a welcoming retail environment.
o Support and guide team members in assisting guests with product selection, offering knowledgeable recommendations to enhance the shopping experience.
o Drive sales by promoting merchandise, special offers, and upselling opportunities.
o Monitor and ensure all guest interactions meet high service standards and brand expectations.
o Address escalated guest inquiries and ensure timely and professional resolution.

• Transaction Management & Cash Handling:

o Oversee and ensure all retail transactions are processed accurately and efficiently using the POS system.
o Monitor cash handling procedures to ensure compliance with company policies and security standards.
o Assist with and review daily cash reconciliation and reporting.
o Support team members with complex transactions, returns, exchanges, and adjustments.
o Ensure accuracy and accountability in all financial transactions.

• Merchandising & Inventory Control:

o Ensure visual merchandising standards are consistently executed and aligned with brand guidelines.
o Oversee inventory levels, stock replenishment, and product availability.
o Supervise receiving, tagging, and organization of new merchandise.
o Assist in conducting inventory counts and maintaining stockroom organization.
o Identify opportunities to improve product presentation and sales performance.

• Operational Support & Store Maintenance:

o Supervise daily retail operations, ensuring the store is clean, organized, and visually appealing at all times.
o Oversee opening and closing procedures, ensuring all tasks are completed accurately.
o Ensure all retail equipment and POS systems are functioning properly and address any issues promptly.
o Maintain operational standards across the sales floor, fitting rooms, and stock areas.

• Guest Satisfaction & Issue Resolution:

o Resolve guest concerns and complaints in a professional and timely manner.
o Handle escalated issues and determine appropriate solutions in alignment with company standards.
o Ensure a consistently positive and seamless shopping experience for all guests.

• Team Leadership & Development:

o Supervise, support, and motivate retail team members to achieve sales and service goals.
o Provide coaching, training, and ongoing feedback to enhance team performance.
o Assist in scheduling, delegation of tasks, and daily workflow management.
o Foster a collaborative and positive team environment.

• Team Collaboration & Communication:

o Partner with management to achieve store goals and operational objectives.
o Communicate product feedback, guest insights, and operational needs effectively.
o Support team initiatives, promotions, and special retail events.

• Health & Safety Compliance:

o Ensure adherence to all company policies related to safety, security, and loss prevention.
o Maintain cleanliness and organization in accordance with health and safety standards.
o Monitor proper handling and storage of merchandise and equipment.

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.