An exceptionally capable and proactive semi-remote Full-Time Executive Personal Assistant/ Executive Household Operations Manager is sought to support a busy, internationally mobile family with multiple residences and a complex range of personal, household and administrative responsibilities. Candidates should ideally be based in New York, where the family spends their summers. Their primary residence during the academic year is Dorado, Puerto Rico, and candidates will be expected to travel here 1 x per month.
The family is looking for an individual who can genuinely add value, anticipate requirements, take ownership of projects, implement systems and processes, and ultimately save the principals considerable time.
The family currently maintains approximately 5–10 properties worldwide, and existing local support is in place, including dedicated property concierges and professional housekeeping services. The successful candidate will be responsible for coordinating these resources, ensuring clear communication and accountability, and making sure that outstanding tasks are followed through without requiring constant input from the principals.
The family is not necessarily looking to establish a formal family office or appoint a traditional Chief of Staff at this stage. However, they would welcome someone with the capability and ambition to grow into a broader operational role over time. This individual should ideally be able to build the infrastructure that allows the family to operate more efficiently.
Responsibilities
Executive and Personal Support
Provide high-level executive and personal support to both principals.
Proactively manage complex calendars, appointments, commitments, and schedules.
Coordinate personal and family travel, working alongside the family's existing travel agent where appropriate.
Manage itineraries, flights, accommodation, ground transportation and travel logistics.
Anticipate requirements and resolve issues before they become problems.
Manage correspondence, communications and follow-ups.
Prepare briefing documents, itineraries, schedules and relevant background information.
Identify opportunities to streamline the principals' day-to-day lives and reduce administrative demands.
Property and Household Management
Oversee the coordination and ongoing management of approximately 5–10 domestic and international properties.
Work closely with existing property concierges and on-site contacts to ensure each residence is maintained to the required standard.
Implement property checklists, maintenance schedules,s and standard operating procedures.
Coordinate contractors, vendors, maintenance teams, and service providers.
Monitor outstanding maintenance issues and ensure timely resolution.
Oversee property readiness ahead of family arrivals and departures.
Coordinate seasonal property openings and closures.
Manage property-related projects and ensure deadlines are met.
Coordinate with rental management companies regarding properties being rented out.
Assist with the preparation and rental coordination of properties in New York and Puerto Rico.
Monitor property-related expenditure and maintain accurate records.
Vendor and Staff Management
Act as a central point of contact for household staff, concierges, vendors, and external service providers
Establish clear lines of communication and accountability.
Source and manage reliable service providers across different locations.
Negotiate where appropriate and ensure value for money.
Monitor service standards and address issues proactively.
Ensure that household operations are running efficiently across all properties.
Travel and Lifestyle Management
Coordinate complex family travel across multiple locations.
Work alongside the family's existing travel agent while retaining ownership of the overall logistics.
Ensure properties, staff, transportation,n and other arrangements are ready ahead of each trip.
Manage changes to itineraries and resolve travel-related…