Executive Personal Assistant ( Remote)

Overview

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A private individual 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.

Schedule Monday – Friday core hours, with occasional weekend or evening availability required for special events or travel (advance notice provided).

This is a fully remote position. The candidate must be available for 2–3 short trips per year to Kauai, Hawaii (typically 5 days each) to support in\-person needs, events, and relationship management. All other work is performed remotely.

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.

Compensation \& Benefits

• Competitive salary (commensurate with experience)
• Comprehensive health insurance
• Generous paid vacation and sick leave
• 401(k) with employer contribution
• Performance\-based bonus
• Annual travel to Hawaii fully covered (flights, luxury accommodations, ground transportation, and per diem)

Key Responsibilities

• 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
• Anticipate needs and solve problems discreetly and efficiently

Requirements

• Bachelor’s degree strongly preferred
• 2–5\+ 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: highly proficient in Microsoft Office/Google Workspace; quick learner of new tools and software
• Outstanding written and verbal communication skills
• Ability to work flexibly across time zones and remain calm under pressure
• Valid passport and willingness to travel 2–3 times per year to Hawaii

About Lily Pond Services

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Lily Pond Services is a premier domestic staffing agency specializing in personalized placement for families. We connect families with experienced, reliable professionals through a trusted and thorough process, ensuring the perfect fit for your unique needs.