Job Overview: A successful, longtime Maui business owner is looking for an organized, professional, and tech-savvy Personal Assistant/Household Manager to become a trusted right-hand person and long-term partner. This is a unique opportunity for someone who enjoys variety in their work, takes initiative, and thrives in a role where no two days are exactly the same.

The principal has spent decades building and managing a successful business and is now focused on simplifying life, consolidating assets, and enjoying greater work-life balance. As a result, this position will play an important role in handling many of the day-to-day details, allowing him to focus on larger priorities. The ideal candidate will be adaptable, resourceful, and comfortable managing both ongoing responsibilities and unexpected needs while taking ownership of the details that keep a busy household running smoothly. While there will be regular administrative and household tasks, this role is not highly structured or micromanaged. Instead, the employer is looking for a proactive professional who can anticipate needs, solve problems independently, coordinate projects, and help keep both personal and household affairs running smoothly.

In addition to supporting the principal's daily life and household operations, the right candidate will occasionally assist with family-related needs. This includes helping coordinate transportation for the principal's active 12-year-old grandson, who participates in various after-school activities, as well as providing occasional support to the family's 94-year-old grandmother with simple tasks and errands. While caregiving is not a primary responsibility of this role, the ideal candidate will be happy to lend a helping hand when needed and become a trusted extension of the family.

As trust is established, the role may expand to include assistance with real estate holdings, property coordination, and special projects as the principal continues to evaluate investment opportunities and manage personal assets.

Key Responsibilities:
• Manage calendars, appointments, scheduling, and travel arrangements.
• Coordinate and manage household operations, vendors, contractors, and service providers.
• Oversee cleaning services and help ensure the home is running efficiently and smoothly.
• Assist with grocery shopping, maintaining household food inventory, and occasional light meal preparation as needed. While the principal currently prepares many of his own meals,

he would appreciate support in keeping the household stocked and simplifying day-to-day meal planning. A private chef may also be considered in the future.
• Assist with administrative tasks, correspondence, filing, and organization.
• Oversee property-related needs, including coordinating repairs and maintenance when needed.
• Assist with errands, special projects, and miscellaneous requests.
• Conduct research, gather information, and provide recommendations for household and business-related decisions.
• Support light bookkeeping and organization of records as needed.
• Maintain household inventory, grocery shopping, and ensure the home is stocked with everyday essentials.
• Anticipate needs and proactively identify ways to improve household efficiency and organization.
• Assist with property management, real estate-related projects, and investment coordination as opportunities arise.
• Provide and coordinate occasional transportation, scheduling, and other support needs for the principal's 12-year-old grandson.
• Provide occasional assistance and support to the family's 94-year-old matriarch as needed.
• Serve as a trusted resource for the principal, helping with day-to-day needs as they arise
• Take ownership of day-to-day household and personal operations, proactively anticipating needs, solving problems, and helping the principal stay focused on larger priorities.

Requirements:
• Previous experience as a Personal Assistant, Executive Assistant, Household Manager, or similar role preferred.
• Highly organized with strong attention to detail and excellent follow-through.
• Tech-savvy and comfortable using computers, apps, and modern communication tools.
• Strong problem-solving skills and ability to work independently.
• Professional, discreet, trustworthy, and dependable.
• Excellent communication and interpersonal skills.
• Flexible and adaptable to changing priorities and requests.
• Clean driving record.

Start Date: July 15, 2026. The principal will be traveling throughout June and anticipates July to be the earliest possible start date. Flexibility may be available for the right candidate.

Expected Job Duration: Long-term / Many years for the right fit

Schedule: Monday-Friday 9 am-5 pm
* Guaranteed 40 hours a week
* Occasional evenings, weekends, vacations

Housing Opportunity: A private guest cottage located on the employer's property may be available as part of the overall compensation package for the right candidate. The cottage features a private 1-bedroom/1-bathroom living space, air conditioning, private laundry facilities, private parking, and a separate entrance. This unique housing opportunity offers the convenience of living close to work while still maintaining privacy and independence, making it an exceptional benefit for someone looking to build a long-term career and life on Maui.

Annual Compensation with Cottage: $100,000 annually DOE, plus a private guest cottage provided as part of the compensation package. The employer is open to discussing the overall compensation structure for an exceptional candidate with the right experience and qualifications.
Hourly Equivalent: $48.08 per hour

Annual Compensation without Cottage: $130,000 annually DOE. The employer is open to discussing the overall compensation structure for an exceptional candidate with the right experience and qualifications.
Hourly Equivalent: $62.50 per hour

Benefits:
Private guest cottage provided
Paid Vacation
Paid Sick Leave
Paid Holidays
Gas Mileage Reimbursement: Candidate will be using their own car for errands.
Health Insurance
Long-term stability and growth opportunities

* Priority will be given to Hawaii-based candidates. Relocation assistance may be considered for an exceptional candidate whose qualifications and experience closely align with the family's needs.