Executive Personal Assistant to UHNW Family Job at Pocketbook Agency, Kauai County, HI

Y3Era3JmMytVRjg4VFdPVStSZ3pvaVhWRnc9PQ==
  • Pocketbook Agency
  • Kauai County, HI

Job Description

JRN: 2083

An active and entrepreneurial UHNW family of five is seeking a highly capable and emotionally intelligent Executive Personal Assistant to work closely with their long-standing family manager, with the goal of taking over the role entirely by January 2026. This is a dynamic, hybrid role that blends personal support, household operations, and executive-level coordination in a fast-paced, private home environment. The position requires a high degree of discretion, flexibility, emotional intelligence, and initiative.

Requirements:

  • 3+ years of experience in private service, executive assistant, or household management roles
  • Emotionally intelligent, discreet, proactive, and calm under pressure
  • Strong organizational and multitasking skills; comfortable managing up
  • Experience working in dynamic family environments
  • Tech-savvy and familiar with tools for scheduling, document sharing, and household operations
  • Flexible and open to a fluid schedule with occasional evening or weekend needs
  • Travel required, international and domestic
  • No formal office; candidate must be comfortable working from a home environment

Responsibilities:

  • Provide seamless administrative and personal support to the principals
  • Manage family calendars, appointments, and travel logistics (domestic and international)
  • Coordinate and liaise with attorneys, charities, vendors, and private service providers
  • Handle household payroll, invoice processing, and light financial administration
  • Oversee and collaborate with household staff, including nannies, property manager, and vendors
  • Support with errands, light household tasks, and children’s needs as needed
  • Book and manage complex travel itineraries, accommodations, and related logistics
  • Maintain documentation, communications, and scheduling for the principals' various projects and engagements
  • Occasionally travel with the family to assist with on-the-ground coordination and support
  • Handle special projects with the utmost confidentiality and care

Schedule: 24/7 mentality required

Compensation: Up to $100K BOE, healthcare stipend, PTO

Location: Primarily based in Hawaii, with travel and partial remote flexibility

Job Tags

Work from home, Flexible hours, Afternoon shift,

Similar Jobs

Macy's

Summer Video Production Assistant Job at Macy's

 ...experience all aspects of Content creation and production. All positions are in person at our Long...  .... Job Title: Video Production Assistant Reports To: Director, Video...  ...support in executing final content from filming, editing, and or both Assist video teams... 

Kyo

Business Data & Finance Analyst (100% Remote) Job at Kyo

 ...Job Description Job Description Use data to drive better decisions. Build tools that...  ...re looking for a Business Data & Finance Analyst who loves turning data into actionable...  ...or Ramp is a plus Benefits ~100% remote, work from anywhere in these states: CA,... 

Woofies

Woofie's Pet Sitter and Dog Walker- Western Loudoun Job at Woofies

 ...Job Description Job Description Calling All Pet Lovers: Join Our Paw-some Team! Must live in the Western Loudoun area Are you a true pet lover looking for a paw-some gig? Woofies of Western Loudoun is expanding and we want YOU to join our team of passionate... 

Arlington HealthCare

Obstetrics & Gynecology Physician Job at Arlington HealthCare

 ...every taste. Family-friendly service and meals can be found at any number of chain restaurants and diners, while a variety of elegant establishments serve cuisines from around the world. Coffee shops, bakeries and ice cream parlors can be found in the area as well.... 

Uniti Med

Travel Mammography Technologist - $1,959 per week Job at Uniti Med

 ...Uniti Med is seeking a travel Mammography Technologist for a travel job in Marietta, Georgia. Job Description & Requirements Specialty: Mammography Technologist Discipline: Allied Health Professional Start Date: 06/16/2025 Duration: 12 weeks Shift:...