Caring Transitions

Executive & Personal Assistant to the Owner/CEO

Ellicott City, MD - Part Time to Full Time

Location: Ellicott City, MD (On-site / Field Hybrid)
Position Type: Part Time to Full-time

The Big Picture
We are a fast-growing local franchise specializing in senior relocation, downsizing, and estate sales. As our business scales, the Owner requires a highly organized, trusted, and proactive right-hand partner to handle day-to-day administrative logistics. 
This role is a unique hybrid: 80% of your focus will be dedicated to business infrastructure, team operations, and client coordination. The remaining 20% will involve managing personal scheduling, travel, and lifestyle logistics for the owner. If you excel in high-trust, fast-paced environments where no two days are alike, we want to hear from you.

Your Day-to-Day Impact
Business Operations & Administration (80%):
  • Team & Office Coordination: Support our fast-growing team of 6+ field employees by coordinating training spaces, managing team schedules, and archiving internal documentation. [1]
  • Financial & Payroll Admin: Assist with bookkeeping by organizing receipts for our CPA, scanning invoices, and verifying automated vendor billing in QuickBooks and Gusto.
  • Vendor & Client Liaison: Act as the primary gatekeeper for office operations, managing relationships with commercial property managers, insurance contacts, and local real estate partners. 
  • Compliance & Logistics Support: Assist with routine corporate governance tasks, state business filings, and tracking required business credentials or certificates.
  • Special Business Projects: Coordinate logistics for regional team training, staff appreciation dinners, and preparation for national brand conferences. [1]
The Lifestyle Architect (20%):
  • Calendar & Travel Management: Manage the owner's integrated personal and professional calendars, booking domestic travel, hotel stays, and dining arrangements.
  • Errands & Household Coordination: Run occasional local errands or coordinate routine service providers (landscaping, maintenance) for the owner's personal properties.
  • Asset Coordination: Assist in tracking personal hobbies, collections, or vehicle maintenance records as needed.

The Perfect Match:
  • Experience: 3+ years of experience as an Executive Assistant, Personal Assistant, Office Manager, or high-end customer service role.
  • Tech Savvy: High proficiency in Google Workspace, Apple ecosystem platforms, and general office productivity tools. Experience with basic business accounting software is a major plus.
  • Locational Flexibility: Must be based near Ellicott City/Columbia, MD with a valid driver’s license and a reliable vehicle for light local travel.
  • Discretion & Trust: Impeccable integrity is required to safely handle sensitive corporate data and private family scheduling.
  • Growth Mindset: Strong problem-solving skills with the ability to build structure in a rapidly scaling business environment.
Apply: Executive & Personal Assistant to the Owner/CEO
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Imagine you are in the middle of verifying a payroll run for our CPA, and leadership simultaneously needs an urgent personal errand run across town. How do you evaluate and prioritize these competing demands?*
Which of the following platforms do you have hands-on experience using? (Select all that apply: Google Workspace, Apple/iOS ecosystem, QuickBooks, Gusto or similar payroll software, CRM/Project Management tools).*
Tell us about a time in a previous role where you noticed a process, calendar, or filing system was unorganized, and you took the initiative to fix it. What did you change, and what was the outcome?
In this role, you will handle sensitive corporate data and private family schedules. Can you share an example of a time you had to maintain strict confidentiality or exercise extreme discretion in a past professional setting?*
How would you describe your communication style when acting as the primary point of contact or 'gatekeeper' for a busy business owner? How do you ensure crucial updates don't fall through the cracks?*
This position requires light local travel around the Ellicott City/Columbia, MD area for administrative and lifestyle support. Do you have a valid driver’s license, a reliable personal vehicle, and a clean driving record?*
Human Check*