About the Role

Seeking a highly organized, detail-oriented, and resourceful Personal Assistant to oversee and manage a dynamic portfolio of personal, family, and household responsibilities. This role supports a busy executive and their extended family across a range of activities including family affairs, travel logistics, household management, medical coordination, inbox and calendar support, philanthropic initiatives, and ad hoc personal and professional projects.

The ideal candidate is proactive, discreet, highly communicative, and comfortable wearing many hats in a fast-paced and evolving environment. You will work closely with family members, household staff, external service providers, and other key collaborators to ensure smooth day-to-day operations across all domains of the family ecosystem.

Key Responsibilities

Medical & Insurance Coordination

• Schedule and manage medical appointments for family members
• Handle all health insurance matters (claims, reimbursements, renewals) for CEO and immediate/extended family
• Liaise with doctors, providers, and insurance companies to ensure proper coverage and timely reimbursements

Travel Management

• Research, book, and coordinate personal and business travel for family members
• Create detailed itineraries including flights, hotels, ground transportation, meals, and activities
• Manage passport/visa renewals and travel documentation
• Track travel-related contracts and expenses

Children, Family & Education Support

• Assist with educational scheduling, extracurriculars, applications, and ongoing deadlines
• Research programs, tutors, and opportunities tailored to children's evolving interests and needs
• Support family members on a variety of personal and professional projects and their respective career developmental activities

Household & Property Management

• Support the management of multiple properties
• Coordinate maintenance, staff, utilities, and vendor relationships
• Manage HOA/club correspondence and billing
• Support rental logistics and property use for guests and family members

Inbox & Communication Management

• Monitor and manage CEO’s personal inbox; draft responses and highlight priorities daily
• Oversee family email correspondence and assist with formal communications
• Track and sort all personal and business mail/correspondence and key documentation

Finance & Administration

• Track and manage personal and family expenses
• Assist with property taxes for all structures within household portfolio
• Assist with documentation needed for tax season (in collaboration with accountants)
• Manage CEO’s business expenses (via RAMP) and maintain expense records for family LLCs
• Subscription management and financial tracking for recurring services

Philanthropy & Events

• Coordinate philanthropic donations, documentation, and communications
• Assist with planning family events, holidays, and special occasions

Qualifications

• Proven experience in executive support, household/family management, or personal chief-of-staff role
• Impeccable attention to detail, organization, and follow-through
• Excellent communication skills, both written and verbal
• Ability to manage multiple priorities with grace and discretion
• Strong tech literacy (Google Workspace, RAMP, Dropbox, etc.)
• Comfortable handling sensitive information with absolute confidentiality
• Self-starter mindset with ability to work independently and problem-solve proactively

Bonus Skills

• Background in project management, event planning, or healthcare coordination
• Experience supporting executives or entrepreneurial families
• Familiarity with travel booking platforms and international logistics
• Interest in education, music, and/or creative arts

This position is being advertised on behalf of a partner organization. Employment terms, benefits, and conditions may vary and are subject to the policies of the hiring company. Details on the specific requirements and conditions for this role will be provided during the recruitment process.