Top 3 Executive assistant to owner Jobs in Easton, Md

Executive & Personal Assistant (Full-Time)
Millman Search Group —Easton, MD
- $75,000 - $100,000 a year
- Weekends as needed
- Google Workspace
- Research
- Mid-level
- Travel reimbursement
- Mileage reimbursement
Quick Apply
6d
Executive Assistant to Owner
Soistman Family Dentistry & Associates —Easton, MD
- $50,000 - $65,000 a year
- Full-time
- English
- Research
- Mid-level
- Health insurance
- Dental insurance
Quick Apply
3d
Fire Sprinkler Fitter Foreman (TRAVELING)
North American Fire Protection —United States
- $30 - $40 an hour
- Overtime
- Background check
- Mechanic experience
- Construction site
- Profit sharing
- Paid training
Quick Apply

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Executive & Personal Assistant (Full-Time)
Millman Search Group —Easton, MD
Reliable transportation and valid driver's license. Active real estate license (even if not currently practicing). Keep CRM/contact systems up to date.
$75,000 - $100,000 a year
Quick Apply
6d
Senior Project Manager - Commercial Drywall & Interiors
Client of JLM HR Consulting LLC —Crofton, MD
Partner with estimators, field leadership, and executive management to ensure seamless project execution. Serve as the primary point of contact for owners,…
$130,000 - $165,000 a year
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3d

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Superintendent - K-12 Construction
Michael Page —Columbus, OH
Modern construction technology including Procore, Bluebeam, drones, and digital field management tools. Experience reviewing and managing RFIs, submittals, shop…
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Executive & Personal Assistant (Full-Time)

Millman Search Group
Easton, MD

Quick Apply

Job Details

Full-time
$75,000 - $100,000 a year
6 days ago

Benefits

Travel reimbursement
Mileage reimbursement
Health insurance
Paid time off
Flexible schedule
Retirement plan

Qualifications

Vendor relationship building
Accounting systems
Google Workspace
Confidential information handling
DocuSign
Executive administrative support
Research
Real Estate License
Driver's License
QuickBooks
Collaborative technology platforms
E-signature software
Productivity software

Full Job Description

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

Quick Apply

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executive assistant to owner jobs in easton, md

Executive & Personal Assistant (Full-Time)

Executive Assistant to Owner

Fire Sprinkler Fitter Foreman (TRAVELING)

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