Copycat Holdings Ltd. is seeking an experienced Personal Assistant to provide assistance to the principal of a private family office based in the Cayman Islands within a UHNW private household environment. Reporting to the Operations Administrator, the Personal Assistant will play a crucial role in supporting the day-to-day domestic operations of the principal and family. It is essential to note that the bulk of this role entails general household and personal support to the principal. This is a highly demanding, UHNW private household position (not an office-based administrative role) requiring consistent reliability, flexibility, utmost discretion, security awareness, and the ability to build and maintain a trusted working relationship across personal, professional, and household matters. A background in security, law enforcement, or military service is required and will be strictly verified prior to interview stage progression. This requirement is non-negotiable and candidates without direct relevant experience should not apply. This role requires frequent after-hours, weekends, and on-call availability across multiple residences and operational requirements. Duties and Responsibilities
Duties and responsibilities include, but are not limited to
General Household & Personal Support
This role requires an individual to work 6 days per week, with work starting at 7:30am. The successful applicant must be available to work on Sundays and public holidays on short notice as may be required or when Principal is on island (this is a non-standard working schedule and not suitable for candidates seeking structured hours or hybrid/flexibility arrangements)
Execute personal errands for the principal and family with efficiency, utmost discretion and attention to detail
Procure and deliver gifts for family and friends, ensuring special occasions and key dates are accommodated, including weekends and holidays
Personal delivery of highly confidential information, both personal and professional along with time sensitive courier pick up/delivery
Assist colleagues with various tasks, projects and requests
Assist with annual holiday preparations and remain available at all times during this period (extended availability required; leave restrictions apply during peak periods)
Role holder is required to take vacation annually at a time when the Principal is off island, subject to operational requirements – vacation notice is to be provided at least 3-4 months in advance due to the principal’s travel schedule
Maintain absolute confidentiality regarding all personal, financial, business and family matters and ensure the privacy and security of the principal and family at all times
Perform such other duties as may reasonably be assigned by the Principal from time to time
Provide security to the principal and family as required from time to time
Household Operations & Management
Oversee all household provisioning, including grocery purchasing, inventory management and replenishment of household essentials
Maintain detailed inventories and registers for household furnishings, artwork, electronics, appliances and tools
Maintenance and co-ordination of multiple residences, including but not limited to management of repairs, staffing requirements and inventory (multi-property UHNW estate experience essential; general property management experience is not sufficient)
Maintain warranty records, service agreements, user manuals and maintenance schedules for all household systems, appliances, vehicles and equipment
Conduct regular inspections of all residences and provide reports regarding maintenance issues, security concerns and operational requirements
Organising and supervising onsite visitors who are conducting maintenance, deliveries, installations and repair projects within multiple residences
Source, obtain quotations from, negotiate with, and manage third-party contractors and service providers as required
Supervising, instructing and training housekeeping staff to consistently deliver five star, white glove service standards and attention to detail across all properties
Maintain household appliances and carry out minor repairs as needed
Monitor and coordinate maintenance of household technology systems, including internet, networking, audiovisual equipment, security systems and smart home platforms
Vehicle Management & Transportation
Manage the full life cycle of multiple vehicles, including maintenance, fueling, insurance, inspections, repairs and detailing (experience with luxury and high-value vehicles required)
Maintain accurate records of vehicle servicing, warranties, registrations and insurance documentation
Ensure all vehicles are kept in roadworthy, fully compliant, and presentation ready condition at all times
Driving principal and family as required and when on island, including airport pick-ups and drop-offs (must demonstrate proven experience and be confident operating high-value vehicles in professional or security sensitive environments)
Assist with transportation logistics, luggage handling and guest arrivals and departures as required
Financial & Administrative Responsibilities
Pay various invoices and trades as requested from time to time for household repairs and maintenance, using cash or company debit card provided
Manage and reconcile petty cash and day to day household expenditures, maintaining clear and accurate financial records
Maintain organized physical and electronic records relating to household operations, expenditures, maintenance and service providers
Liaising with insurance companies and ensuring all policies and documents are up to date
Security, Emergency Preparedness & Customs
Hurricane preparations during storm season for main residence and other properties, including ensuring all storm protection measures, supplies, and procedures are in place
The individual in this role is required to remain on island during a storm, subject to any emergency evacuation notices issued by Cayman Islands Government (mandatory operational requirement; no discretion for relocation during active storm events unless instructed by authorities or principal)
Conduct regular inspections of the residence and other properties throughout the year and during storm season to ensure security, safety, and overall readiness
Maintain and regularly inspect emergency first aid kits, medical supplies and emergency preparedness equipment in all residences and vehicles, ensuring all items remain fully stocked and within expiry dates
Assist with the coordination and processing of customs clearance for furniture, artwork, household, and residential items
Assist with the coordination and documentation required for Importing and Exporting luxury vehicles
Assist with maintaining multiple luxury vehicles, including insurance, servicing, licensing, repairs, refueling
Guest & Hospitality Services
Assist with planning and coordination, setup and breakdown of private family and social events, including dinners, parties, and recreational activities such as boat trips, including providing supplies and coordinating with outside event planners, as requested by the principal and family (this role includes frequent after-hours and weekend operational demands)
Requirements Experience
Previous long-term experience in a private family environment for high net worth individuals (minimum 5+ in a dedicated UHNW private household or family office environment required)
Previous experience managing multiple luxury residences, vehicles, and supervising household staff (multi-property estate management experience is essential)
Must have proven experience independently handling matters with Cayman Islands Customs, licensing authorities, utility providers and government departments
Previous security, law enforcement, or military service is required, with a strong understanding of situational awareness and experience operating in security sensitive environments (non-negotiable requirement; equivalent private security experience will not be considered unless explicitly approved by hiring principal)
Certifications & Physical Requirements
Applicant must hold valid CPR and AED certification throughout employment
Must be physically fit and able to safely lift and carry items up to approximately 50 lbs as part of regular duties
Must have a clean, valid driver’s license and maintain eligibility to drive at all times
Valid passport and ability to travel internationally if required
A clean police clearance certificate is a prerequisite and must remain valid as required by the principal and governing authorities
Skills & Technical Knowledge
Excellent organizational and time management skills with the ability to prioritize effectively, manage concurrent responsibilities, and consistently meet tight deadlines in a fast paced environment
Willing and able to assist at various hours of the day, including evenings, weekends and holidays, with no fixed schedule and rapid response outside standard working hours
Excellent verbal and written communication skills, with the ability to draft professional correspondence, manage external communications, and represent the principals interests appropriately
Proficient in Microsoft Office applications, particularly Excel, with preferred bookkeeping or financial record keeping
Must be knowledgeable in the Apple suite of products and provide basic troubleshooting, setup, and day to day support for Apple devices and household entertainment systems, including televisions and audiovisual equipment
Must have knowledge of and experience using Savant home automation systems, including the management of lighting, climate control, security, entertainment, and remote access functionality
Must have knowledge of hurricane preparedness procedures, property storm shuttering and post storm recovery operations
Professional Attributes
Must possess a high degree of discretion, integrity and professionalism at all times. A security-conscious mindset is essential, with prior experience in security, law enforcement, or military service
Must be a self-starter and able to manage multiple tasks and competing priorities simultaneously
Must be highly responsive and able to manage urgent matters with discretion and speed when required (including time-sensitive and high-pressure situations)
Must be confident, professional, polite, and respectful at all times, with excellent communication and interpersonal skills, and sound judgement in all interactions
Demonstrated ability to exercise discretion and handle highly confidential information (any breach of confidentiality will result in immediate termination)
Strong problem solving skills and the ability to work independently with minimal supervision
Additional Requirements
Must be able to provide 3 professional references
Sign a stringent Non-Disclosure Agreement with significant obligations covering all personal, financial, business and household matters relating to the principal and family
Applicants must be at least 30 years of age
This is a full-time, exclusive engagement. The successful candidate will be required to dedicate working capacity to this position and must not engage in any secondary employment or external professional commitments during employment
