PowerToFly
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 documentationTrack 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.
What PowerToFly.com Has to Offer PowerToFly supports a fully remote team and core coverage with country specific benefits. This may include health care, a retirement savings plan, parental and adoption leave and perks such as self-directed budgets to support learning and growth. We also offer unlimited personal time off and mentorship opportunities.
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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 documentationTrack 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.
What PowerToFly.com Has to Offer PowerToFly supports a fully remote team and core coverage with country specific benefits. This may include health care, a retirement savings plan, parental and adoption leave and perks such as self-directed budgets to support learning and growth. We also offer unlimited personal time off and mentorship opportunities.
#J-18808-Ljbffr