Executive Personal Assistant to UHNW Family ( {{city}}) Job at Pocketbook Agency, Kauai County, HI

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  • 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

Remote job, Flexible hours, Afternoon shift,

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