Guest Experience Supervisor

The Islands of Islamorada•Islamorada, Village of Islands, FL

1d•Onsite

About The Position

The Guest Services Supervisor is the heartbeat of the front-of-house experience at The Islands of Islamorada. This role is responsible for ensuring seamless, warm, and memorable interactions at every guest touchpoint — from pre-arrival communication and check-in through departure and beyond. The ideal candidate leads by example on the floor, supports and develops the Guest Services team, and embodies the resort's commitment to anticipatory, personalized service. This is a hands-on supervisory role that requires equal parts hospitality instinct, operational precision, and genuine care for people.

Requirements

Minimum 2 years of front desk or guest services experience in a hotel or resort environment, with at least 1 year in a supervisory or lead capacity.
Demonstrated ability to lead a team with warmth, professionalism, and clear direction.
Proficiency with Property Management Systems (PMS); experience with Infor HMS, Opera, or similar platforms preferred.
Exceptional communication skills — written, verbal, and interpersonal — with a natural ability to connect with diverse guests.
Strong problem-solving skills and the ability to remain composed under pressure in a fast-paced, high-service environment.
Flexible availability including evenings, weekends, and holidays in alignment with resort business demands.

Nice To Haves

Experience in a boutique, independent, or luxury resort environment with a strong emphasis on personalized service.
Familiarity with guest feedback tools (Revinate, TripAdvisor, Google Reviews) and shift communication platforms (Breezeway Messaging or similar).
Associate's or Bachelor's degree in Hospitality Management or related field.
Bilingual (English/Spanish) a plus given the resort's Keys and Miami drive market guest profile.

Responsibilities

Serve as an empowered on-floor leader during assigned shifts, ensuring all guest interactions meet or exceed The Islands of Islamorada service standards.
Anticipate guest needs and resolve concerns promptly, professionally, and with genuine empathy — escalating to management when appropriate.
Oversee pre-arrival communication and villa/suite preparation coordination, ensuring guest preferences and special requests are confirmed and executed.
Conduct property orientation and welcome experiences that reflect the resort's boutique character and Florida Keys spirit.
Supervise daily activities of Front Desk Agents and Concierge team members during assigned shifts including check-in/check-out procedures, gift shop sales, room assignments, and billing accuracy.
Lead daily pre-shift meetings with the Guest Services team to align on arrivals, special requests, VIP notes, and service priorities.
Support the onboarding and ongoing training of new team members, including service standards, PMS systems, and property knowledge.
Provide real-time coaching and constructive feedback to team members; recognize and celebrate service excellence.
Assign daily tasks, monitor shift productivity, and ensure tasks and checklists are completed accurately and on time.
Maintain thorough knowledge of property amenities, local area attractions, dining, watersports, and experiential offerings to serve as a trusted resource for guests.
Coordinate with Housekeeping, Maintenance, F&B, and Recreation departments to ensure smooth interdepartmental communication and seamless service delivery.
Monitor villa and suite inventory, manage upsell add-ons/packages, and support the front office's contribution to occupancy and revenue goals.
Maintain accurate shift logs and complete required reporting for management review.
Support the implementation of resort-wide initiatives including new experiential offerings, seasonal programming, and VIP arrivals.