Executive Personal Assistant (RELOCATION)

Yutori Method

United States

On-site

USD 70,000 - 80,000

Full time

14 days+

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Benefits offered by this job

Comprehensive benefits package

Relocation expenses reimbursement

Leadership training participation

Job summary

A dynamic business support organization is seeking an Executive Personal Assistant to manage the household of a busy entrepreneur. You will handle scheduling, travel coordination, and communication with household staff while ensuring routines run smoothly. This full-time role requires strong organizational skills and at least two years of experience as an Executive Assistant. A competitive salary and comprehensive benefits package are offered.

Qualifications

Two years in a Personal/Executive Assistant role required.
Five years administrative/project management experience required.
Experience with ChatGPT or similar technology required.

Responsibilities

Coordinate household and family activities, appointments, and logistics.
Maintain organized documentation and manage calendars effectively.
Book and manage travel arrangements for the principal and family.

Skills

Project management experience

Strong communication skills

Organizational skills

Time management

Coordination skills

Education

Bachelor's degree or equivalent

Tools

Google Suite

Microsoft Suite

1Password

Notion

Job description

Overview

Executive Personal Assistant (RELOCATION) — Yutori Method is managing the recruitment for this role. This position is a full-time, in-person leadership role based in Frederick, MD. Candidates must be willing to commute.

About

TCS Interpreting and Captioning — A leading provider of American Sign Language (ASL) interpreting and captioning services, TCS delivers high-quality, reliable language access solutions for clients across sectors. Known for its professionalism, accuracy, and commitment to accessibility, TCS serves as a trusted partner for organizations requiring clear and effective communication for Deaf and hard-of-hearing communities.

Young Entrepreneur Council (YEC) — An exclusive, invitation-only community for high-achieving entrepreneurs. YEC provides members with access to a trusted network, publishing opportunities, private events, and a robust suite of business resources designed to accelerate success.

About the Role

This is a unique and exciting opportunity for a high-caliber Personal Assistant to lighten the load for a dynamic entrepreneur, ensuring her household of four children, partner, pets, and staff runs seamlessly while supporting her leadership across multiple thriving businesses. You will own the personal and professional calendars, coordinate travel, maintain inbox zero, and ensure action items are completed. You’ll manage household logistics — from meal planning and vendor coordination to family events and children’s activities — all while anticipating needs and protecting Jessica’s time for her highest-impact work.

If you thrive on being the primary point of contact for personal matters and working closely with household staff, vendors and the Chief of Staff to ensure smooth daily operations and timely follow-through, this role offers the chance to make a meaningful impact in streamlining systems that keeps the focus on high-level priorities.

What You’ll Do

Personal & Household Property Logistics

Coordinate family, household, and pet appointments, manage property maintenance, and oversee special events.
Manage household budget, subscriptions, errands, supply inventory, and meal prep coordination with staff.
Liaise with household team to ensure smooth daily operations, updated schedules, and execution of routines and systems.

Administrative

Maintain inbox zero, track action items, manage documents, and upload critical files to shared systems.
Provide meeting support, follow up on tasks, and coordinate with the Chief of Staff and ops team for continuity.
Organize personal and business resources for quick access and effective execution.

Calendar & Scheduling

Manage professional and personal calendar, aligning energy and priorities while accounting for family schedules.
Coordinate meetings, family events, and children’s activities with appropriate time buffers.
Plan date nights, family activities, and weekly rhythm reviews.

Travel Coordination

Book and manage personal and business travel for principal, family, and companions, including childcare needs.
Create detailed itineraries and ensure all travel preferences and VIP perks are utilized.
Oversee loyalty programs, points, and other travel benefits for optimized use.

Knowledge & Skills

Bachelor's degree or equivalent - PREFERRED
Two (2) years in a Personal/Executive Assistant role - REQUIRED
Five (5) years administrative/project management experience - REQUIRED
ChatGPT (similar) - REQUIRED
Google Suite - REQUIRED
Microsoft Suite - REQUIRED
1Password - PREFERRED
Notion or similar - PREFERRED
American Sign Language - PREFERRED

Logistics & Compensation

Work Hours: 9:00 AM – 5:00 PM EST (flexibility required as needed)
Expected Start Date: 10/1/25
Compensation: $70,000-$80,000
Relocation Expenses: $5,000 repayment
Must have valid Driver's license
Benefits: Comprehensive benefits package shared with finalists; participation in leadership training and programs
Authorization: Must be authorized to work in the U.S. without sponsorship
Accommodations: Reasonable accommodations available for qualified individuals with disabilities

Seniority level