Full-Time Traveling Executive Personal Assistant

| Kauai, HI, United States

Posted Date 4/06/2026
Description

Job Title:           Full-Time Live-Out Traveling Executive Personal Assistant

Reporting to:    The Principal

Start:                 ASAP

Location:           Kauai, Hawaii

Hours:               Monday through Friday, business hours, 40 to 45 hours per week; must be flexible and responsive after hours and weekends as needed

Salary:              $155,000 - $170,000 per year

Benefits:            Partial housing stipend, $500/monthly medical stipend or medical insurance, 401k retirement, PTO, sick days, and main federal holidays

The Family:        The principal and her three sons, 11, 10, and 4-years-old; it is a split family dynamic, this role will also assist her ex-husband

Pets:                   No pets

The Home:        The property in Kauai is 3,000sq ft, 4 bedrooms, and has a guest house

The Staff:          Household Manager, Nannies, and Housekeepers

Travel:              Extensive travel domestic and international; common destinations include, Los Angeles, NYC, Italy, Australia, and elsewhere; typically short trips, except for summers are spent 6-8 weeks away, this role will likely be expected to be with the principal the whole duration

Relocation:        Family will consider candidates that live in Hawaii and California; will cover relocation to Kauai; may also opt to live in nearby Oahu; temporary housing will be provided for the first 90-days

 

Key Responsibilities*

Please find your primary responsibilities outlined below:

*Please note the below list is not exhaustive.

 

General Administrative

  • Preparing appropriate, efficient and timely responses to all the principal’s requests, whether made in person, electronically or otherwise
  • Managing access to employer by screening, drafting, and issuing correspondence on their behalf
  • Heavy calendaring and efficient planning week to week; ensuring principals are aware of all appointments and are fully prepared.
  • Coping with last minute changes/requests, working to pre-empt and resolve potential scheduling conflicts
  • Assisting with projects and research as required
  • Ensuring availability and flexibility, including managing last minute requests beyond office hours, over the weekend and holidays

 

Day to Day Management

  • Knowledge of household security and smart home systems
  • Ability to perform all tasks of staff under management and fill in as needed
  • Work with and coordinate things with Household Manager

 

Family Assistance

  • Monitoring deliveries and arranging returns
  • Assisting with service during events and family gatherings
  • Sorting mail, separating junk
  • Approaching work with a ‘never having to ask’ attitude – proactively completely jobs and pre-empting the family’s needs.

 

Occasional Childcare

  • May, on rare occasions, need to step in to supervise the children if the nanny on duty calls out

 

Staff Supervision

  • Assist the household manager in their absence with overseeing staff as appropriate
  • Assist with onboarding and training staff
  • Forging relationships with the family and household staff & becoming a trusted ‘go to’ person when needed

 

Household Budget & Bill Pay

  • Maintaining the household budget and keeping a record of all household expenses – preparing expense reports
  • Assisting with household bill pay
  • Liaise with bill payment team, all 3rd party provider accounts, ensuring punctual payments
  • Reconcile credit card statements

 

Travel & Event Planning

  • Help coordinate all aspects of family travel: flights, accommodations, itineraries, reservations, and ground transportation with the principals (commercial and private)
  • Maintain and update family calendars with social engagements, appointments, and travel plans
  • Travelling domestic and international as needed
  • Property set up: travelling ahead of the family and/or coordinating with on-site staff, to ensure the house is ready - supplies are ordered, relevant staff know their duties, suitcases are unpacked – ensuring the house is fully ready
  • Assist with planning and coordinate social and family events, including managing logistics and vendor communications with the principals; this includes social plans with friends, birthdays, and dinners, etc.

 

Requirements:

  • A clean valid driver’s license (may have access to house vehicle for errands)
  • Legally able to work within the United States
  • Must have experience working in a similar role for HNW private families
  • Must be tech savvy
  • Must have heavy calendaring and travel planning experience (commercial and private)
  • Must have household budget and bill pay management experience
  • Excellent references required
  • Confidentiality/non-disclosure agreement
Job Type
Full-Time
Job Categories
Executive Assistant | Personal Assistant
Housing
Live-out
Compensation
$155,000 - $170,000 per year; relocation; partial housing stipend, $500/monthly medical stipend or medical insurance, 401k retirement, PTO, sick days, and main federal holidays

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