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.

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 issues.
• Coordinate family activities, seasonal arrangements and holiday logistics.
• Assist with the practical organization of skiing holidays in Montana and other family trips.


Systems, Processes and Operational Improvement

• Review existing administrative and household processes and identify opportunities for improvement.
• Develop and implement standard operating procedures (SOPs) across properties and household operations.
• Create centralized systems for tracking tasks, projects, maintenance, vendors, and household requirements.
• Establish clear reporting structures and accountability.
• Develop efficient systems to ensure tasks are completed without repeated follow-up from the principals.
• Identify opportunities to automate or outsource administrative tasks.
• Build scalable systems that can accommodate the family's evolving requirements.
• Provide regular updates and recommendations to the principals.


Financial and Administrative Coordination

• Coordinate property-related invoices and expenditure.
• Maintain organized records of household and property expenses.
• Assist with budget tracking and financial administration.
• Coordinate with accountants and other external advisers as required.
• Help establish processes for managing recurring payments, bills, and property expenses.
• Potentially take on greater responsibility for bill payment and financial administration over time, as the family becomes comfortable delegating these functions.


Family and Lifestyle Coordination

• Provide occasional support with family-related logistics and activities.
• Assist with coordinating the children's wider extracurricular schedules where necessary, working alongside other household staff.
• Ensure family commitments, travel and property arrangements are coordinated seamlessly.
• Act as a trusted, discreet and dependable point of contact

• Bachelor's degree from a recognized university preferred.
• Significant experience in a senior Executive Assistant, Private PA, Executive Operations, or Household Operations role.
• Ideally, 8+ years of relevant experience supporting UHNW individuals, entrepreneurs, principals, or private families.
• Experience managing multiple properties, vendors, and external service providers is highly desirable.
• Demonstrable experience implementing systems, processes, and operational improvements.
• Strong project management and organizational skills.
• Excellent written and verbal communication skills.
• Financial and administrative literacy, ideally including experience with expense tracking and budgets.
• Experience coordinating complex domestic and international travel.
• Excellent IT skills, including Microsoft Office, Google Workspace, and relevant project management platforms.
• Experience working across multiple time zones and locations.
• A proven track record of working independently and taking ownership of responsibilities.


The successful candidate will be someone who can operate at a high level and genuinely take responsibility for making the family's lives easier.

Key attributes include:

• Exceptionally proactive, resourceful, and solutions-oriented.
• Able to think independently and make sound decisions without constant direction.
• Ability to identify efficiencies and cost-saving opportunities.
• Highly organized, with outstanding attention to detail.
• Strong project management capabilities.
• Comfortable managing multiple priorities and complex projects simultaneously.
• Able to establish processes and systems from scratch rather than simply following existing instructions.
• Confident managing vendors, contractors, household staff and external advisers.
• Strong interpersonal and communication skills.
• Discreet, trustworthy and accustomed to handling confidential personal and financial information.
• Comfortable working with a high degree of autonomy.
• Flexible and adaptable, with a willingness to travel when required.
• Able to build a strong, trusted relationship with both principals.
• Must be comfortable working within an evolving role that may expand as trust and responsibility develop.


• $170,000+ per annum, depending on experience
• Comprehensive benefits package - medical, dental, vision + 401 (k)
• All other industry-standard benefits
• Discretionary performance-related bonus.
• Private accommodation in Dorado when required.
• Potential for increased responsibility and professional development into a broader Executive Operations / Chief of Staff position.