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Executive Personal Assistant

to CEO (and Spouse)

Job ID: 3441988

About The Job

We are seeking a dynamic, high-level Executive Personal Assistant to support a CEO based in Baltimore, MD. This is a full-time role that blends traditional executive support with high-touch personal assistance. The ideal candidate thrives in fast-paced environments, can pivot seamlessly between business and personal matters, and understands how to bring order and calm to a complex, ever-changing schedule.

 

This is a Monday through Friday position, typically from 8:30 AM to 5:30 PM, though flexibility is key. Some evenings, weekends, and occasional travel may be required depending on the CEO’s calendar. The right candidate will have experience supporting C-level executives, an impeccable command of logistics and discretion, and a service-oriented mindset.

 

The Executive Personal Assistant will be the CEO’s right hand in all aspects of life and business—from managing inboxes and high-level communications, to overseeing family logistics, coordinating travel, running point on property vendors, and supporting the CEO’s spouse with social, household, and philanthropic obligations.

The Employer

The principal is a high-performing CEO leading a mid-sized private company with a national footprint. His schedule is demanding and fluid, with travel, investor meetings, speaking engagements, and company offsites. The CEO is sharp, gracious, and expects clear communication, high efficiency, and trusted judgment from his inner circle.

 

This is a newly created role that reflects the growing need for integrated support across his professional and personal life. The Executive Personal Assistant will work closely with internal staff including the Chief of Staff, Executive Assistant to the company, household service providers, and other stakeholders. The role also includes support for the CEO’s spouse, who maintains an active calendar of social, philanthropic, and volunteer commitments.

Responsibilities

Executive Support

 

  • Coordinate and manage the CEO’s business and personal calendar, ensuring seamless scheduling across both spheres
  • Monitor and respond to emails, flag time-sensitive items, and draft communications as appropriate
  • Serve as liaison between the CEO and internal/external stakeholders, handling requests with discretion and professionalism
  • Assist with board materials, investor relations prep, and travel itineraries in coordination with the CEO’s corporate Executive Assistant
  • Track high-level follow-ups, outstanding decisions, and long-range planning items

 

Personal & Family Support

 

  • Manage the family’s personal calendar, travel coordination, and household appointments
  • Provide support to the CEO’s spouse on errands, personal correspondence, event prep, and charitable initiatives
  • Oversee family gifting, including sourcing, shipping, and seasonal planning
  • Coordinate medical appointments, home maintenance, and other personal commitments
  • Run errands and provide in-person support for tasks that require local attention

 

Travel & Event Planning

 

  • Handle end-to-end logistics for personal and professional travel, including flights, lodging, ground transport, dining, and itinerary documents
  • Ensure seamless execution of social events, dinners, and gatherings at home or offsite (including working with caterers, vendors, florists, etc.)
  • Prepare briefing materials or packing lists for trips, ensuring all logistics are covered

 

Home & Vendor Oversight

 

  • Manage relationships with vendors including housekeepers, landscapers, tech support, security, and seasonal services
  • Oversee vendor scheduling, access, and follow-through, ensuring high standards are maintained
  • Track maintenance calendars, subscription renewals, warranties, and home projects
  • Act as point-of-contact for urgent household needs or deliveries, especially when the family is traveling

 

Special Projects

 

  • Research and coordinate ad hoc projects ranging from school applications to real estate needs, nonprofit initiatives, or private travel experiences
  • Assist with digital organization, from file management to streamlining personal accounts and systems
  • Maintain and update contact lists, preferences, and key reference documents

Must Haves

  • 5+ years of experience as a Personal or Executive Assistant, preferably supporting a CEO, entrepreneur, or high-profile individual
  • Strong interpersonal instincts and excellent written and verbal communication skills
  • Extremely detail-oriented, organized, and proactive
  • Proven discretion, trustworthiness, and ability to manage sensitive information
  • Confident with Mac and PC environments, cloud-based tools (Google Workspace, Dropbox, Evernote, etc.), and digital calendar systems
  • Local to the Baltimore area with reliable transportation and ability to travel locally for errands or vendor coordination
  • Flexibility to respond to occasional needs outside business hours or during travel

About You

  • You anticipate needs before they’re spoken and bring order to chaos
  • You’re professional, polished, and calm under pressure
  • You understand what makes a CEO tick and know how to protect their time
  • You’re just as comfortable in a boardroom as you are at the dry cleaner or handling a sensitive family matter
  • You’re grounded, discreet, and highly organized—able to manage multiple priorities with grace
  • You get things done quietly and efficiently, without needing constant direction
  • You enjoy variety, problem-solving, and being the go-to person others rely on

Compensation & Benefits

  • Salary range of $100,000 to $130,000, commensurate with experience
  • Annual bonus eligibility based on performance
  • Comprehensive health benefits including medical, dental, and vision insurance
  • 401(k) with employer contribution
  • Paid time off (vacation, sick days, floating holidays, and federal holidays)
  • Discretionary travel and professional development opportunities
  • Phone and laptop provided; travel expenses reimbursed

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At A Glance

  • Baltimore, MD
  • Full-Time
  • $100,000-130,000

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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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Adam Cook
Founder & Managing Director

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