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Executive & Personal Assistant to the Owner/CEO

Caring Transitions
Caring Transitions Salary
Ellicott, MD Full Time
POSTED ON 6/25/2026
AVAILABLE BEFORE 12/20/2026
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

Salary.com Estimation for Executive & Personal Assistant to the Owner/CEO in Ellicott, MD
$58,575 to $72,915
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