Job Description

JRN #: 2664

We are seeking a service-driven Weekend Travel Personal Assistant to support a private family across residences within New York. This hands-on role travels with the family most weekends and makes every trip run smoothly, from packing and setup to solving issues on the ground. Trips may include family residences, hotels, and domestic or international destinations. The ideal candidate is a chief stewardess or a celebrity PA who loves high-level service, not only the desk work. This role offers strong exposure and room to grow.

Responsibilities:

• Travel with the family and serve as the go-to resource on weekends and during moves between residences.
• Pack, unpack, and set up for each trip. Manage luggage, wardrobe prep, garment care, and personal items.
• Travel ahead to prepare destinations and residences before the family arrives.
• Plan transportation, lodging, dining, activities, and appointments.
• Build and maintain itineraries, packing lists, checklists, contacts, and confirmations.
• Anticipate needs, including clothing, sports equipment, and special requests.
• Track travel plans and fix delays, cancellations, missing items, and vendor changes on your own.
• Handle errands, purchases, returns, deliveries, reservations, and special requests.
• Keep records of travel preferences, memberships, loyalty programs, and trusted vendors.
• Work closely with the office team and another PA during the week to stay aligned.
• Help refine repeatable processes for packing, property transitions, and weekend coverage.

Qualifications:

• 3+ years as a chief stewardess, travel PA, celebrity PA, or in a similar high-touch service role.
• Strong service skills and comfort with hands-on, non-desk work.
• Experience coordinating complex travel, logistics, and schedules.
• Valid passport and ability to travel often.
• Highly organized, proactive, and detail-oriented.
• Calm and flexible when plans change.
• Warm, polished, and highly discreet.
• Strong communicator with the team, vendors, and principals.
• Bachelor's degree preferred, or equivalent experience.

Location: New York, NY. Fully in person. Open to candidates relocating.

Schedule: Full-time, 45 to 55 hours per week. Generally Thursday through Monday, with weekend travel and midweek days off. Some evenings and holidays as needed.

Compensation: $120,000 to $160,000 DOE, plus year-end bonus. Room to grow.

Benefits: Health, dental, and vision insurance, 401(k) with match, and lunches provided.

Pocketbook Agency is acting solely as a recruiting and placement firm for this position and is not the employer of record for this role unless otherwise explicitly stated. All hiring decisions, compensation, benefits, and employment terms are determined by the client employer. By applying, you acknowledge that submission of an application does not guarantee placement or employment.

Pocketbook Agency is an equal opportunity recruiting firm and does not discriminate in its recruiting, screening, or placement practices based on race, color, religion, sex, gender identity, sexual orientation, national origin, age, disability, veteran status, or any other protected characteristic under applicable law.

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