ABOUT THE JOB
We are looking for an experienced Executive Personal Assistant with deep property/vendor management experience, who is comfortable working in close partnership with a principal who has clear preferences and a defined way of doing things. She will share an office with the principal and become the person she relies on to keep information flowing, maintain order, and ensure that her home, projects, and personal affairs move forward appropriately. Someone who listens closely, communicates thoughtfully, and is a true professional will thrive here.
The position blends traditional executive and personal support with significant property and vendor management. The principal’s primary residence is in Washington DC, which is where the assistant will be based, but she also owns properties in Michigan, New York, and Massachusetts. The assistant will coordinate with service providers and staff at all four properties to provide oversight over the four properties, while providing seamless executive support to the principal in a 1:1 capacity.
This role is also an opportunity for the assistant to support the principal’s philanthropic work and assist in building out the operations of her foundation. The assistant will take on research, special projects, contact and document management, and the day-to-day communication flow that keeps everything running smoothly.
Schedule
The schedule is Monday through Friday, 9-5pm. The principal values routine, and clear work-life boundaries, which makes this a rare opportunity to work in a senior level position with stability and predictability.
THE EMPLOYER
The principal is a Washington DC resident with longstanding ties to the region and an active personal, civic, and philanthropic life. Her DC home is her primary residence, though she spends part of each week in New York for work and retreats to homes in Massachusetts and Michigan during the summer and holidays. Her DC residence is supported by a household team that includes a long tenured houseman and two housekeepers.
Her standards are high, and her style is direct. She appreciates someone who is organized, steady, observant, and able to keep pace with her structured approach to managing both her home and personal affairs. While she is private and discerning, she values relationships and responds well to someone who communicates clearly, respects her preferences, and supports her in a way that feels seamless, thoughtful, and aligned.
RESPONSIBILITIES
Executive & Personal Support
- Partner closely with the principal in a shared workspace and maintain a calm, professional presence throughout the day
- Professionally represent and interface with the principal’s family, friends and colleagues at all times
- Support the management of her calendar, coordinating meetings and logistics at her request
- Maintain and update contact lists, emergency contacts, and key information repositories
- Prepare written updates and summaries, using the principal’s preferred structure
- Draft correspondence, notes, and written materials with excellent penmanship and attention to detail
- Review, route, and track bill pay and expenses in coordination with the principal’s wealth manager
- Handle mail, scanning, filing, photocopying, document organization, and other administrative tasks
- Support research, archives, writing projects, and other special initiatives
- Assist with the operational buildout of her foundation and help coordinate fundraising and philanthropic activity
Property/Vendor Management
- Maintain oversight of the DC residence, ensuring that household staff and vendors meet the principal’s expectations
- Coordinate directly with the houseman and housekeepers, providing leadership and structure while respecting existing relationships/workflows
- Manage property calendars, maintenance schedules, punch lists, warranties, contracts, and household documentation
- Liaise with service providers and contractors at all properties, ensuring accurate communication and follow through
- Source, vet, schedule, and supervise vendors as needed, securing competitive bids and monitoring performance
- Maintain property files, budget documents, maintenance logs, and renovation records
- Support landscaping and grounds programs as needed, coordinating mowing, pruning, seasonal changes, irrigation, and pool or hot tub maintenance
- Advance properties as necessary to prepare for the principal’s and/or guests’ arrival
- Monitor safety procedures and security systems and communicate all relevant updates to the principal
- Support ongoing special projects, storage inventory, and organizational improvements across properties
MUST HAVES
- 7-10 years of relevant experience supporting a private principal or family in a high touch environment
- Strong administrative foundation, including document management and digital/paper filing
- Excellent written communication skills and neat penmanship (sample expected)
- High proficiency with Apple products, iCal, spreadsheets, and general home office technology
- Experience managing household staff and multiple vendors with confidence and tact
- Comfort working in close physical proximity to a principal each day
- Ability to maintain strict confidentiality, discretion, and a need-to-know mindset
- Professional polish, sound judgment, and the ability to work steadily alongside a strong personality
ABOUT YOU
- You are organized, intuitive, and observant, with a talent for picking up preferences quickly
- You have a calm, centered presence and do not get rattled by direct communication
- You enjoy creating order, managing information, and keeping systems running smoothly
- You take pride in being a reliable right hand and in building trust with a principal
- You are capable of managing multiple properties, deadlines and personalities both in-person and from afar
- You understand high standards and can uphold them without ego or pushback
- You communicate clearly and succinctly, both verbally and in writing
- You are protective of your principal’s privacy and operate with humility and judgment
- Spanish speaking is a plus for communicating with staff and vendors
- Excellent references and a history of longevity in past positions required
COMPENSATION & BENEFITS
- Salary of $150,000 (depending on experience)
- Annual performance bonus opportunity
- Health insurance provided with full employee coverage
- 13 paid holidays each year
- 10 days paid time off (PTO)
This position is listed by Old State Staffing, the Mid-Atlantic’s #1 referral agency for household, child & family-care, executive/personal support and family office staff. With over 40 years of experience placing exceptional candidates with successful families and individuals, we represent roles that are as dynamic and tailored as the families we support. Our principals value discretion, professionalism, and long-term success, and we provide candidates with insight, guidance, and ongoing support throughout the hiring process. Learn more at www.oldstatestaffing.com.
Pay: $150,000.00 per year
Benefits:
- Health insurance
- Paid time off
Application Question(s):
- Please briefly describe any experience you have providing house management to a principal (1-2 sentences).
- Please briefly describe any experience you have providing executive assistance to a principal (1-2 sentences).
- This position is based in NW Washington, DC. Are you local to DC or are you considering relocation for this position?
Work Location: In person
