Personal Assistant to Private Principal

We are seeking an experienced, polished, and highly proactive Personal Assistant to support a private principal at their residence in Baltimore County, Maryland. This is an exciting opportunity for someone who enjoys wearing multiple hats and serving as a true right hand, helping to keep every aspect of the principal's personal life running seamlessly. The ideal candidate is exceptionally organized, resourceful, and service-oriented, with a natural ability to anticipate needs before they arise.

This role requires someone who is equally comfortable managing calendars, coordinating travel and vendors, running errands, organizing the home, planning events, and handling a wide variety of personal and administrative requests with professionalism and discretion. You'll work closely with the principal and existing household staff to ensure everything behind the scenes operates effortlessly.

• Provide high-level personal and administrative support to the principal across all aspects of daily life
• Manage an ever-changing calendar, appointments, reservations, reminders, and personal commitments
• Coordinate domestic and international travel, including itineraries, accommodations, transportation, and logistics
• Oversee grocery shopping, household inventory, and ensure the residence remains fully stocked and organized
• Coordinate household vendors, service providers, deliveries, maintenance appointments, and home projects
• Run personal errands, manage returns, dry cleaning, shipping, mail, and other day-to-day requests
• Research, source, purchase, and coordinate gifts for holidays, birthdays, and special occasions
• Assist with planning and coordinating small gatherings, family events, and entertaining as needed
• Track purchases, receipts, reimbursements, and outstanding follow-up items
• Serve as a liaison between the principal, household staff, vendors, and outside professionals
• Prepare the residence for the principal's arrival, guests, and special occasions
• Anticipate needs, solve problems proactively, and continually look for ways to improve efficiency
• Handle all personal, household, and family matters with the highest level of discretion and confidentiality

• 7+ years of relevant Personal Assistant, Executive Assistant, or similar experience
• Exceptional organizational, time management, and prioritization skills
• Outstanding verbal and written communication abilities
• Strong calendar management and travel coordination experience
• Excellent judgment with the ability to work independently and anticipate needs
• Warm, polished, and professional demeanor with a service-first mindset
• Ability to collaborate effectively with household staff, vendors, and outside professionals
• Tech-savvy with proficiency in Microsoft Office, Google Workspace, smartphones, shared calendars, and task management platforms
• High degree of discretion, integrity, and professionalism when handling confidential matters
• Positive attitude with a no-task-too-small approach

Full-time, 40 hours per week. This role is primarily based at the principal's residence in Baltimore County, Maryland, with flexibility required based on the principal's schedule. Occasional evenings and weekends may be required with advance notice whenever possible.

Up to $200K depending on experience, healthcare coverage, PTO

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.