Summary
PERSONAL ASSISTANT
CAYMAN ISLANDS WITH TRAVEL
Essential Requirements: Minimum of 5 years working as a private PA, excellent communication and time management skills, flexibility to travel.
Our client is seeking an experienced, highly discreet, and resourceful Personal Assistant (PA) to support the principal of a family office based between the Cayman Islands and New York City. This is a dynamic, hands-on role requiring exceptional organisational ability, sound judgment, and a deep understanding of the lifestyle, pace, and expectations of UHNW individuals and families.
The ideal candidate will have a flexible mindset regarding both location and daily responsibilities. Experience managing demanding personal calendars, coordinating private air travel, and organising luxury experiences for both adults and children is essential. A key part of the role also includes oversight of multiple residential properties in New York and the Cayman Islands, ensuring they are maintained to the highest standards.
Key Responsibilities
• Manage complex personal and family calendars across multiple time zones (NYC and Cayman)
• Coordinate all aspects of travel logistics, including private aviation, hotel bookings, visas, and itineraries
• Organise social and cultural outings for the principal, spouse, and children (e.g. baby-friendly activities, fine dining, entertainment, events)
• Handle reservations and secure access to exclusive venues, clubs, and experiences in NYC and the Caribbean
• Oversee the day-to-day management and maintenance of multiple high-end residential properties in New York and the Cayman Islands
• Liaise with household staff, vendors, contractors, and service providers to ensure all properties are running smoothly and maintained to luxury standards
• Ensure homes are guest-ready at all times, including managing household inventories, seasonal preparation, and event hosting needs
• Provide ad hoc personal support including errands, gifting, special occasions, and personal shopping
• Ensure absolute discretion and confidentiality at all times
• • Knowledge of New York City, including key venues, services, and logistics relevant to UHNW households, would be highly advantageous
Candidate Profile
• Minimum 5+ years’ experience supporting a UHNW family, C-suite executive, or in a private family office
• Proven experience with property and household management across multiple residences
• Impeccable organisational and time-management skills
• Ability to operate with complete discretion, sound judgment, and adaptability
• Experience booking and coordinating private aviation and luxury travel logistics
• Able to travel frequently between New York City and the Cayman Islands; flexibility to work outside of standard hours as required
This role is based in the Cayman Islands with frequent travel. Top negotiable salary based on experience, along with medical insurance and accommodation. (HU4311)
