Executive & Personal Assistant

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