Now Seeking a Dynamic Managing Director of Lead an Exciting Mixed-Use Development at the Stunning Islands of Islamorada!

Compensation: Highly competitive salary and highly attainable bonus program!

This is an Exciting Opportunity for a high energy Managing Director to lead unique Mixed-Use Development in Islamorada, FL. Join us on Upper Matecumbe Key to shape a community that includes Residential, Marina, Resort, HOA and Guest Experience Amenities. Showcase your exceptional team-building prowess to create an unforgettable environment for guests and associates alike. Plus, Housing Provided!

What You will be Doing

  • As Managing Director, you will ensure smooth and efficient operations and exceptional guest experiences.
  • Your daily tasks will include overseeing various departments, budget management, building relationships with the HOA and resolving guest issues.
  • You will report to the Vice President of Operations.

The Ideal Candidate for this Position

The ideal candidate is a hands on leader with experience in a Residential/Condo environment coupled with Hospitality Guest Activation Experiences. This candidate should have a background in Hospitality with the ability to lead Revenue Development with Channel Management and Food and Beverage while maintaining a luxury cleanliness standards and conditions.


  • Must be a citizen of this country or possess a valid work permit.
  • Requires a minimum of 4 plus year of leadership experience in a hotel environment.
  • HOA/Condo Environment Experience, Required.
  • Hospitality Experience, Required
  • Applicable State Licensing, Required. 
  • Position will be required to work a varied schedule that may include evenings, nights, and weekends.
Additional Requirements:
  • Experience managing and completing hotel Accounting & HR responsibilities.
  • Track record driving and meeting GSS.
  • Consistently exceed revenue and guest expectations.
  • Ability to manage change effectively.
  • Provide leadership to position the property to achieve the mission.
  • Provide leadership to the departments to achieve their goals and objectives.
  • Communicate the goals and objectives and inspire associates to achieve those goals.
  • Clear, concise written and verbal communication skills.
  • Ability to sell concepts and ideas to management, peers, and associates.
  • Maintain a good working relationship with guests, groups, and personnel from other departments.
  • Demonstrate team building experience and lead by example.
  • Participative management style.
  • Proven successful leadership experience.
  • Abilities to inspire, train, and develop people for promotion.
  • Experience training associates.
  • Instill a guest service attitude in all associates with a "can-do" attitude.
  • Coach associates how to resolve and deescalate conflicts.
Educational Requirements:
  • BA/BS 4-5 year degree or foreign equivalency or combination of experience and education.

Our Associates Love

  • Managing Director Villa, Included! 
  • Amazing opportunities for career advancement across HVMG
  • Up to 40% earned wages paid BEFORE payday with PayActive
  • Flexible Time Off Policy
  • Full Healthcare Benefits (including medical, dental, and vision coverage)
  • 401k Retirement Plan with a guaranteed 4% match and no vesting
  • Hotel and Food and Beverage Discounts and Perks

An Equal Opportunity Employer. We provide equal opportunity without regard to race, color, national origin, religion, sex, age, marital status, or disability. EOE/AA.

The Islands of Islamorada

82779 Old Highway
Islamorada, FL 33036

Telephone (305) 440-3255