Executive & Personal Assistant to the Owner/CEO

Caring TransitionsEllicott City, MD
$19 - $22Hybrid

About The Position

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.

Requirements

  • 3+ years of experience as an Executive Assistant, Personal Assistant, Office Manager, or high-end customer service role.
  • High proficiency in Google Workspace, Apple ecosystem platforms, and general office productivity tools.
  • Must be based near Ellicott City/Columbia, MD with a valid driver’s license and a reliable vehicle for light local travel.
  • Impeccable integrity is required to safely handle sensitive corporate data and private family scheduling.
  • Strong problem-solving skills with the ability to build structure in a rapidly scaling business environment.

Nice To Haves

  • Experience with basic business accounting software is a major plus.

Responsibilities

  • Support our fast-growing team of 6+ field employees by coordinating training spaces, managing team schedules, and archiving internal documentation.
  • Assist with bookkeeping by organizing receipts for our CPA, scanning invoices, and verifying automated vendor billing in QuickBooks and Gusto.
  • Act as the primary gatekeeper for office operations, managing relationships with commercial property managers, insurance contacts, and local real estate partners.
  • Assist with routine corporate governance tasks, state business filings, and tracking required business credentials or certificates.
  • Coordinate logistics for regional team training, staff appreciation dinners, and preparation for national brand conferences.
  • Manage the owner's integrated personal and professional calendars, booking domestic travel, hotel stays, and dining arrangements.
  • Run occasional local errands or coordinate routine service providers (landscaping, maintenance) for the owner's personal properties.
  • Assist in tracking personal hobbies, collections, or vehicle maintenance records as needed.
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