PERSONAL ASSISTANT
CAYMAN ISLANDS with travel to New York

Job Reference: HU4311

Essential Requirements: Minimum of 5 years working as a private PA, extensive knowledge of New York City, excellent communication and time management skills, legal to work in USA, availability 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 that requires exceptional organizational ability, sound judgment, and a deep understanding of the lifestyle, pace, and expectations of UHNW individuals and families.

 The ideal candidate will be deeply familiar with New York City - its geography, social and cultural calendar, family-friendly venues, and high-end service providers. They will also have experience managing demanding personal calendars, coordinating private air travel, and organizing luxury experiences for both adults and children. A core part of this 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

  • Organize 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

Candidate Profile

  • Minimum 5+ years’ experience supporting a UHNW family, C-suite executive, or in a private family office

  • Extensive knowledge of and networks within New York City’s social, culinary, and lifestyle scene

  • Proven experience with property and household management across multiple residences

  • Impeccable organizational 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 is a dual-location role between Cayman Islands and New York, you will be required to travel frequently between locations. Top Salary paid in USD.  Medical Insurance. Generous Bonus. Housing will be provided on Grand Cayman. (HU4311)