Director of Guest Experience

Southernmost Beach Resort
Key West, FL

: Compensation Type: Yearly Highgate Hotels: Highgate is a leading real estate investment and hospitality management company widely recognized as an innovator in the industry. Highgate is the dominant player in major U.S. gateway cities including New York, Boston, Miami, San Francisco and Honolulu, with a growing Caribbean and Latin America footprint. The hospitality forward company provides expert guidance through all stages of the property cycle, from planning and development through recapitalization or disposition. Highgate has a proven record of developing its diverse portfolio of bespoke lifestyle hotel brands, legacy brands, and independent hotels and resorts with 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 consisting of some of the most experienced hotel management leaders, the company is a trusted partner for top ownership groups and major hotel brands. Highgate maintains corporate offices in New York, Chicago, Dallas, London, Miami, and Seattle. Location: Located in historic Old Town, Southernmost Beach Resort expands over 6 acres on a serene part of the island with Atlantic Ocean front views, gorgeous Key West architecture, and all the amenities you desire in a beach resort. Just a short walk or bike ride from Key West's boutique shops, art galleries, eclectic restaurants, and non-stop nightlife, the resort spans over two city blocks and offers guest rooms that are located within easy reach of both the beach and world-famous Duval Street. Overview: A Director of Experiences is responsible for overseeing the development and implementation of Resort initiatives that improve customer relations and loyalty. This person will serve as the Resort's cultural liaison and will be responsible for the coordination of all activities to include cultural programming, entertainment, kid's activities, and pool/beach programming. In this role he/she is responsible to supervise and oversee the strategy, planning and execution of the Resorts overall guest experience goals. He/She must plan, coordinate and service activations to engage the Resort guests to ensure customer satisfaction while maintaining profitable operations and high-quality service levels. Candidates must be comfortable in problem solving with guest relationships and activation management. Candidate must be outgoing, passionate, energetic, and innovative with the activities offered and dedicated to creating memorable experiences to drive repeat guests and revenue. Responsibilities:
  • Create Resort goals to improve the guest experience. Serve as the resort's cultural liaison.
  • Keep immediate supervisor fully informed of all problems or matters requiring his/her attention.
  • Prepare and submit required reports in a timely manner.
  • Meet with top-level executives and department heads to discuss potential plans and initiatives to implement activations.
  • Conduct research to find out more about guest behavior and preferences at the resort.
  • Coordination of all resort activities to include cultural programming, entertainment, kids' activities, pool/beach programming
  • Create and manage the Resort's Calendar of activities to include daily, weekly, special events and other evening activities.
  • Create new retail concept with Southernmost/Property brand, and increase retail revenues
  • Build a streamlined guest experience across all departments.
  • Figure out ways to increase guest satisfaction and build Resort loyalty.
  • Collect and analyze data to make well-informed business decisions.
  • Motivate team members to engage with the guests to help create experiences while pushing for success and positive guest feedback.
  • Have comprehensive knowledge of all operational departments within the hotel? Guest services, reservations, housekeeping, accounting, food and beverage and engineering.
  • Interact with outside vendors for activations as needed. Liaison between resort and 3rd party operators for programming and outdoor classes.
  • Work with operations team to activate the Resort for guests and keep the teams informed of issues as they arise.
  • Be visible on the floor and assist staff as needed during activations.
  • Assist with ensuring all invoices are paid in a timely manner; document all payments.
  • Help with and organize fundraising and community activities to support the department.
  • Maintain accurate office and activity supply inventories.
  • Ensure all equipment and supplies are kept in good condition.
  • Be involved in and/or conduct departmental and hotel training (One-to-One Training, etc.)
  • Use feedback from guest evaluations/surveys to improve service and quality and learn more about their experience with the Resort.
  • Participate in required M.O.D. program as scheduled.
Qualifications: Education & Experience:
  • At least 4 years of progressive experience in a hotel or a related field? Or a 2-year college degree and 3 or more years of related experience? Or a 4year college degree and at least 2 years of related experience.
  • At least 3 years of cultural programming experience in hotels/or resorts
  • Must be proficient in Windows, Company approved spreadsheets and word processing and in the operation of all hotel-specific systems.
Physical requirements:
  • Flexible and long hours sometimes required.
  • Weekends and Holidays sometimes required.
  • Medium work Exerting up to 50 pounds of force occasionally, and/or 20 pounds of force frequently or constantly to lift, carry, push, pull or otherwise move objects

General Requirements

  • Must be able to effectively communicate both verbally and written with all levels of employees and guests in an attentive, friendly, courteous and service oriented manner.
  • Must be effective at listening to, understanding, and clarifying concerns raised by employees and guests.
  • Must be able to multitask and prioritize departmental functions to meet deadlines.
  • Approach all encounters with guests and employees in an attentive, friendly, courteous and service-oriented manner.
  • Attend all hotel required meetings and trainings.
  • Participate in M.O.D. coverage as required.
  • Maintain regular attendance in compliance with Highgate Hotel Standards, as required by scheduling, which will vary according to the needs of the hotel.
  • Maintain high standards of personal appearance and grooming, which include wearing nametags.
  • Comply with Highgate Hotel Standards and regulations to encourage safe and efficient hotel operations.
  • Maximize efforts towards productivity, identify problem areas and assist in implementing solutions.
  • Must be effective in handling problems, including anticipating, preventing, identifying, and solving problems as necessary.
  • Must be able to understand and evaluate complex information, data, etc. from various sources to meet appropriate objectives.
  • Must be able to maintain confidentiality of information.
  • Perform other duties as requested by management.

Posted 2026-06-24

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