We are seeking a part-time Executive/Personal Assistant to take over the administrative and financial management of a senior principal’s personal affairs. The role is currently held by his longtime Personal Assistant, who is retiring, and the family is looking for someone who can step in thoughtfully, learn the existing systems, and become a steady long-term support.
Duties include scheduling, keeping track of his email and correspondence, bill pay, trust and tax coordination with his accountant and lawyer, payroll administration, and organizing both current and past personal and business records — all while being a steady, in-person presence for the principal.
Schedule
We are looking for a commitment of approximately 15 to 20 hours per week, with some flexibility based on the candidate’s own schedule, the rhythm of the household, and occasional project needs. Because the principal relies primarily on in-person communication, most of the work will be performed on-site in Georgetown. There may be flexibility for remote work over time once the person is fully settled in.
The principal is a retired general contractor in his mid-80s, based in Georgetown. He is a highly educated gentleman who likes to do things his own way and responds best to someone who is proactive, good-humored, clear, and genuinely invested in supporting him and his family over the long term.
There is a separate, dedicated office behind the residence that will serve as the Personal Assistant’s primary workspace. The principal’s caregiving team handles his day-to-day personal care and household needs, so this role is focused specifically on administrative, financial, organizational, and coordination support.
Administrative
Financial Management
Other
This role tends to suit a particular kind of background. You might be a retired Hill staffer or scheduler who’s used to managing sensitive information and keeping a lot of moving pieces organized. You might be a former full-time assistant or bookkeeper looking for something smaller in scope. Whatever your path, you likely:
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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:
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.
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.
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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.
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Adam Cook
Founder & Managing Director
