Job Description

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
• Asana (similar PM system) - REQUIRED
• 1Password - PREFERRED
• Notion or similar - PREFERRED
• American Sign Language - PREFERRED

Logistics & Compensation

• Location: in person Frederick, MD
• 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

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