Executive Personal Assistant / Estate Manager

to Private Principal

Job ID: 3990021

About The Job

This is a high trust role 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 become the person she relies on to keep information flowing, maintain order, and ensure that her home, projects, and personal affairs move forward seamlessly. Someone who communicates thoughtfully and approaches each day with calm professionalism will thrive here.

 

The position blends traditional executive and personal support with property and vendor management. The principal’s primary residence is in Washington DC, which is where the assistant will be based out of, but she also has homes in Michigan, New York, and Massachusetts. The assistant will coordinate with service providers and staff in DC, as well as the other properties to manage schedules, maintain records, and ensure that everything meets the principal’s expectations.

 

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 strictly Monday through Friday, 9-5pm. The principal values privacy, routine, and clear boundaries, making 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/groundskeeper and two housekeepers.

 

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 highly values relationships and responds well to someone who communicates clearly, respects her preferences, and supports her in a way that feels thoughtful and seamless.

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 presence and do not get rattled by direct communication
  • You have a sense of humor, and thoroughly enjoy what you do professionally
  • 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 $130,000+ (depending on experience)
  • Annual performance bonus opportunity
  • Health insurance provided with full employee coverage
  • Federal holidays provided
  • 10 days paid time off (PTO)

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The world is spinning faster every day.

Employment has changed drastically the past few years—how we work, the type of work we do, and even where we work. Yet, while the world adapts, solutions for hiring private staff seem to be stuck in the past.

 

At Old State Staffing, we believe the status quo is not enough, and that those who decide now is the time to settle will be left behind. In the face of great change, tinkering around the edges simply won’t do. Since Day 1, our approach has been built on four key principles:

1. Developing A Quality Product

We’ve built Old State Staffing from the ground up, implementing the same cutting-edge recruiting tools used by the nation’s largest family offices. Historically inaccessible to smaller clients, these tools improve the tracking and management of talent, utilize machine learning for smarter searches, and intuitively compare compensation and qualification benchmarks both regionally and nationally. This allows us to find and match families with the best candidates quicker and more efficiently than ever before.

2. Building A Great Team

We knew from the start that our team would be our greatest differentiator. That’s because our agency is composed entirely of family office professionals who know what exceptional candidates look like; because we’ve applied to, managed, and hired for each of those positions ourselves.

3. Creating Meaningful Relationships

Building and maintaining relationships is important today, more than ever before. We place immense value on our relationships, not just with our clients, but our candidates, and the community at large. We spent our “pandemic years” building partnerships with local universities, to open the doors of private staffing to recent college graduates in the most educated metropolitan area in the world.

4. Refusing To Settle

Change is inevitable, yet private staffing has historically lagged in both hiring and employment standards. We’ve always been disruptors, first to adopt AI and machine learning—ensuring smarter, faster, more accurate matches for our clients.


We know that choosing an agency is a personal decision, and we’re honored for the time you have spent considering us as a partner in your search. If you haven’t spoken to us yet, let me be the first to say that we can’t wait to introduce you to our contacts, to guide you through the hiring process, and to introduce you to the perfect candidate. We know the stakes are high, but so are the rewards. With Old State Staffing you’ll be empowered to make informed, meaningful hiring decisions, so you can continue to thrive in a world that’s spinning faster every day.

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