Executive Personal Assistant; Kauai, Hawaii

A distinguished private individual based in Kauai, Hawaii, is seeking an exceptional Executive Personal Assistant (EPA) to provide discreet, proactive, and highly professional support across both personal and business matters. This is a rare opportunity for a poised, detail-oriented, and adaptable professional to become a trusted right hand in a dynamic, high-standard environment. The ideal candidate thrives in a full charge setting, anticipates needs before they arise, exercises impeccable judgment, and maintains absolute confidentiality at all times.

Monday - Friday core hours, with occasional weekend or evening availability required for special events or travel (advance notice provided) Based on Kauai or willing to relocate (preferred); must be able to work on-site and separate housing provided. This is a long-term career opportunity for someone who takes genuine pride in creating order, exceeding expectations, and becoming an indispensable partner to the principal.

• Competitive salary (commensurate with experience)
• Comprehensive health insurance
• Generous paid vacation and sick leave
• 401(k) with employer contribution
• Performance-based bonus
• Relocation assistance available for the right candidate

• Act as the primary point of contact between the principal, household staff, vendors, service providers, and external partners
• Manage a complex, ever-changing calendar with precision – scheduling appointments, meetings, and personal engagements
• Plan and coordinate seamless domestic and international travel, including flights, ground transportation, luxury accommodations, visas, and detailed itineraries
• Organize private dinners, gatherings, and special events – liaising with chefs, florists, caterers, entertainment, and other high-end vendors
• Oversee personalized gifting, high-end procurement, and bespoke purchases
• Maintain household and office inventories; procure supplies and manage vendor relationships
• Handle invoice approval, expense tracking, and vendor vetting for property maintenance and services
• Run local errands (driving required), including shopping, deliveries, and appointments
• Anticipate needs and solve problems discreetly and efficiently

• Bachelor's degree strongly preferred
• 1-5 years of experience as an Executive Assistant, Personal Assistant, Chief of Staff, or similar role supporting a high-net-worth individual or C-suite executive
• Exceptional organizational, time-management, and problem-solving abilities
• Absolute discretion and a proven track record of handling sensitive information
• Tech-savvy: proficient in Microsoft Office/Google Workspace; quick learner of new tools and software
• Outstanding written and verbal communication skills
• Valid driver's license and clean driving record
• Ability to work flexibly and remain calm under pressure