PERSONAL ASSISTANT Based in Cayman Islands with Travel to New York

PERSONAL ASSISTANT
Based in Cayman Islands with Travel to New York

Salary: $160,000 – $180,000 USD annually, with full benefits

Housing: On-site housing or housing stipend offered on Grand Cayman

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Essential Requirements:

• Minimum 5 years’ experience as a private Personal Assistant

• Extensive knowledge of New York City lifestyle, culture, and social scene

• Excellent communication, organizational, and time-management skills

• Legal to work in the USA

• Availability to travel frequently between Cayman Islands and New York

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Our client is seeking an experienced, highly discreet, and resourceful Personal Assistant (PA) to support the principal of a family office based primarily in the Cayman Islands, with regular travel to New York City. This dynamic, hands-on role demands exceptional organizational skills, sound judgment, and a deep understanding of the lifestyle, pace, and expectations of ultra-high-net-worth individuals and families.

The ideal candidate must be extremely well connected in New York and fully understand the city’s lifestyle, including trendy social venues, top restaurants, stylists, and concierge-level networks. They will expertly manage demanding personal calendars, private air travel, and curate luxury experiences for the principal and family across both locations.

A key aspect of this role involves overseeing multiple high-end residences in New York and the Cayman Islands, ensuring properties are maintained to the highest standards and always guest-ready.

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Key Responsibilities

• Manage complex personal and family calendars across multiple time zones (NYC and Cayman Islands)

• Coordinate all travel logistics including private aviation, hotels, visas, and detailed itineraries

• Organize social, cultural, and family-friendly outings (fine dining, entertainment, exclusive events)

• Secure reservations and access to exclusive clubs, venues, and experiences in NYC and the Caribbean

• Oversee day-to-day management and maintenance of multiple luxury residential properties

• Liaise with household staff, vendors, contractors, and service providers to maintain property standards

• Manage household inventories, seasonal preparations, and event hosting requirements

• Provide ad hoc personal support such as errands, gifting, personal shopping, and special occasions

• Maintain absolute discretion, confidentiality, and professionalism at all times

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Candidate Profile

• Minimum 5+ years supporting UHNW families, C-suite executives, or within a private family office

• Deep connections and knowledge of New York City’s social, culinary, and lifestyle networks

• Proven expertise in multi-property and household management

• Impeccable organizational, time-management, and problem-solving skills

• Ability to operate with discretion, sound judgment, and adaptability under pressure

• Experienced in booking private aviation and coordinating luxury travel logistics

• Flexibility to travel frequently and work outside standard hours as required

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This is a dual-location position based primarily in the Cayman Islands with frequent travel to New York City.

Competitive salary paid in USD, full medical insurance, generous bonus structure, and housing provided on Grand Cayman.

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