Overview

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

Apply

To Apply

Lily Pond Services welcomes all qualified candidates to pursue our current open positions and apply to those of interest. For a full list of positions, please see below or click below or follow the link listed below: In addition, kindly review the following helpful information prior to submitting your application:

Nondisclosure Information:

Due to the highly discreet nature of each position and the confidentiality required for all of our jobs, no personal information will be provided regarding our clients until further interview stages have been reached. Please keep in mind, some positions may require candidates to submit a Confidentiality/Nondisclosure Agreement.

Application Timeline:

Once an application has been received for processing, candidates will receive a verification email. If we feel your experience suits the needs of the position, we will reach out to you. Please understand that an in-person interview may be required.

No-fee Policy:

Candidates will never be charged a fee from Lily Pond Services LLC for applying to a position listed on our website or entering into a contract with one of our clients after completing the interview process.

Pre-Interview Check-list:

If you are invited to an interview, please be prepared with the appropriate documents and information, including: - two printed copies of your resume or work history - printed letters of recommendations (optional) - photo ID - proof of employment authorization, such as a Green Card

Please upload your CV/resume in .pdf, .doc or .jpg or any other relevant file. .docx is not supported for security reasons Max. file size: 2 MB.

About Lily Pond Services

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.