Executive & Personal Assistant (Full-Time)
Location: St. Michaels, MD (Eastern Shore) — must live locally and be available on-site
Schedule: Full-time, standard business hours with flexibility as needed; occasional evening/weekend availability may be required
Compensation: $75,000–$100,000 annually, commensurate with experience, plus benefits
Reports to: Owner/Principal
About the Role
We're looking for a highly capable, tech-savvy Executive & Personal Assistant to support a serial entrepreneur who has founded and operates a group of companies spanning marketing technology, e-commerce, manufacturing, and consumer services (including brands with hundreds of employees across multiple states), alongside a personal portfolio of real estate investments. This is a hands-on, high-trust role for someone who can manage complexity independently — you'll be given outcomes to own, not tasks to be told how to do. A background in real estate is a significant advantage, as the role will involve coordinating personal investment property matters alongside standard executive and personal support.
This role is ideal for an experienced, highly autonomous EA/PA — for example, someone with a real estate agent, broker, transaction coordinator, or property management background — who wants a full-time role with real scope and ownership rather than routine task execution.
Key Responsibilities
Executive Support
- Manage calendars, scheduling, and meeting coordination across multiple businesses
- Handle correspondence, phone/email triage, and follow-up on behalf of the owner
- Coordinate travel logistics (personal and business)
- Track expenses, invoices, and basic financial paperwork; liaise with bookkeepers/accountants as needed
- Prepare documents, briefing materials, and light research as requested
Personal Support
- Coordinate household vendors, contractors, and service providers
- Manage personal appointments, errands, and scheduling
- Assist with travel planning, reservations, and event/gift coordination
- Act as a trusted point of contact for personal matters requiring discretion
Real Estate Support (Strongly Preferred)
- Serve as a point of contact for a personal portfolio of real estate investment properties
- Liaise with agents, brokers, title companies, and property managers on owned or managed properties
- Track contracts, leases, closings, insurance renewals, and key deadlines
- Coordinate maintenance, inspections, and vendor relationships for investment properties
- Support light due diligence or research on potential new acquisitions as needed
- Bring working familiarity with MLS, transaction timelines, and standard real estate documentation
Business Operations Support
- Maintain organized digital records and files across multiple companies and business entities
- Keep CRM/contact systems up to date
- Support light bookkeeping, document tracking, and administrative operations
- Help coordinate communication and follow-ups across the owner's various businesses and leadership teams as needed
- Anticipate needs proactively rather than waiting for direction
What We Need From You
- 3+ years of experience as an Executive Assistant, Personal Assistant, Transaction Coordinator, or similar high-autonomy support role
- Real estate background strongly preferred — licensed agent/broker, property management, or transaction coordination experience is a major plus
- Genuine tech fluency (non-negotiable): comfortable with tools like Google Workspace or Microsoft 365, scheduling apps, e-signature platforms (DocuSign), expense/accounting tools, and able to learn new software quickly without hand-holding
- Demonstrated ability to work independently — this role has minimal day-to-day supervision by design
- Excellent written and verbal communication
- Discretion and trustworthiness with confidential business and personal information
- Based in or near St. Michaels / Talbot County and able to work on-site regularly
- Reliable transportation and valid driver's license
Nice to Have
- Active real estate license (even if not currently practicing)
- Experience supporting a business owner across multiple companies/entities
- Notary public certification
- Familiarity with QuickBooks or similar accounting software
Compensation & Structure
- $75,000–$100,000 annually, depending on experience (open to discussion for an exceptional real-estate-credentialed candidate)
- Full-time position with standard business hours and some flexibility
- Health insurance contribution, PTO, and retirement plan participation
- Mileage reimbursement for errands/travel on behalf of the owner
Pay: $75,000.00 - $100,000.00 per year
Benefits:
- Flexible schedule
- Health insurance
- Paid time off
- Retirement plan
Work Location: In person
