Executive Assistant to the CEO

Executive Assistant to the CEO

Full-Time | In-office | Millersville MD

Reports to: The CEO directly

Location: In-office, Millersville, MD, Monday through Friday, 8:30 AM – 5:00 PM

Compensation: $60,000- $70,000 base quarterly performance bonus

Also included: Company card for approved business purchases, plus mileage reimbursement

Benefits: Paid Time Off

The Role

This role is the right hand to the founder and CEO of an established Maryland home services company with a growing portfolio of business ventures. You will be responsible for managing the calendar, travel, correspondence, and day-to-day professional and personal administration, along with bookkeeping support and office coordination. You are supporting one person, not a department.

It is a wide role and it moves fast: a flight booked at 9, an attorney followed up with at 11, a return run at 1, a client gift ordered at 3, a set of receipts coded at 4. If you like variety and you like finishing things, this is a very good seat. If you want a narrow lane, it isn't.

You will also sit at the front of a small office. As the CEO spends more time working remotely, you will be the main presence in the building, coordinating day-to-day operations, team events, and visitors, and making sure everyone who interacts with our office, whether team members, clients, or guests, has a positive, professional experience. That part matters to us as much as the logistics.

What you'll own

Calendar and time

● Full ownership of a demanding executive calendar — scheduling, gatekeeping, conflict resolution, and protecting deep-work focus time

● Meeting prep: agendas, materials, background, logistics

● A daily 30-minute sync with the CEO to align priorities and hand off new work

Travel

● All business and personal travel, booked and confirmed end to end, domestic and international

● Complete itineraries (flights, hotels, ground, contacts, reservations) delivered before departure, with backups identified

● Prior experience booking executive travel is required

Personal and household

● Personal appointments, vendors, and life administration

● Coordinating household staff and services — scheduling, groceries and supplies,

keeping everyone pointed in the same direction

● Booking and coordinating family help when it is needed

● Shopping, purchases, returns, deliveries and errands — in person when needed

● Keeping all necessary parties updated on anything that affects the household calendar

● Listing and selling personal and company equipment, vehicles, and personal property

Real estate, entity and document administration

This part of the role is document management, organization, and follow-through, working

alongside our attorneys, CPAs, and other advisors.

● Following up with attorneys, lenders, CPAs, title companies and county offices until

you have an answer — politely and persistently

● Entity administration: LLC formation follow-through, registered agents, EINs, state

filings, annual reports, franchise taxes

● Tracking properties and assets to the right entities and keeping the ownership records

straight

● Closing and refinance document collection and tracking

● Coordinating with the insurance broker as ownership and assets change

● Keeping a document library that is actually organized — deeds, operating

agreements, loan documents, policies, filings

● A compliance calendar loaded twelve months forward so nothing ever lapses

Bookkeeping

● QuickBooks Online for the CEO's personal books and affiliated entities

● Receipt capture, transaction coding, bill entry, missing document follow-up, and a

monthly close package

● You enter and prepare. The CEO approves and releases every payment — you will

not have check-writing authority.

● Prior QuickBooks experience required. You do not need to be an accountant, but you

do need to be accurate.

Network and professional memberships

● Registrations, deadlines, RSVPs, prep materials, and event logistics for professional

memberships and networking groups

● LinkedIn: connecting with people from the CEO’s chapters and events, keeping the

profile current, staying on top of current contacts, new contacts and follow-ups

● Scheduling and on-site setup support for podcast and content shoots

Office, culture and the people in it

● We're a small company where people know each other, and the office experience

matters. This part of the role is about running it well: thoughtful events, timely

recognition, and a well-organized space for team members and guests

● Company culture: offsites, holiday parties, team events, birthdays and work

anniversaries, employee recognition, client and partner gifting

● Office stocked, organized and genuinely nice to be in — snacks, supplies, decor

The inbox

● Full ownership of the CEO's personal email account — not triage and hand back, but

own it

● You review the CEO's email daily; anything that needs attention is identified and

reaches him within 24 hours. This is the most important thing this role does; nothing

important sits unseen.

How we operate

We run on three values that shape how we hire and how we evaluate. Because this role works so closely with the CEO, you'll live them daily.

● Customer obsession. In this seat your customers are the CEO, the team in the

office, and every attorney, lender, vendor and partner you deal with on his behalf. How

people experience working with you is part of the job.

● Operational excellence. Things are done properly, documented, and repeatable. If

you do something twice, it should have a system by the third time.

● Extreme ownership. When something is yours, it is yours — including when

something goes wrong. No excuses, you don't wait to be asked, you flag problems

early, and you see things through to completion.

What this role is not

● Not an operations or management role. This is a dedicated executive assistant

position.

● Not property management.

● Household and family coordination means arranging and scheduling help, not

providing care yourself.

Who this is for

● You have supported a founder, owner or senior executive before and you are

comfortable at that altitude — talking to attorneys, lenders and CPAs without being

handed a script.

● A background in real estate, title, or as a legal or paralegal assistant is a real

advantage here — if you have kept closing files, entity documents or case files

organized for someone, a lot of this will feel familiar. Construction experience is not

needed or expected.

● You finish things. All of them. Including the boring ones, and including the weeks

nobody is watching.

● When you are stuck or you do not know something, your instinct is to ask immediately

— not to set it aside and hope.

● You use AI tools every day and you can show us how you use them. This is a real

requirement, not a nice-to-have.

● You are organized to a degree other people notice, and your systems outlast your

enthusiasm for them.

● You are genuinely comfortable with the full range of this job. There is no task here that

is beneath anyone.

● You hold confidences absolutely — personal, financial and business.

● You have a valid driver's license and reliable transportation. You'll be out running

errands regularly.

● There is an expectation of weekend communication and responsiveness, Saturday

and Sunday 8 AM to 6 PM, with a two-hour acknowledgment standard. We will talk

about it openly in the first interview.

Who this is not for

● Anyone who needs close supervision or frequent follow-up to see things through.

● Anyone looking for a stepping stone into operations or management. This is a

dedicated, career executive assistant role.

How we hire

Our process begins with a first-round recorded virtual interview. Selected candidates will then be invited to an in-person interview with the CEO, and finalists to a paid half-day work trial and reference calls, followed by an offer of employment for the candidate chosen.

The work trial is about four hours and is paid hourly for all time worked. We would rather find out what working together is actually like than guess from a conversation.

We are an equal opportunity employer. We consider all qualified applicants without regard torace, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other characteristic protected by law. If you need an accommodation during the application or interview process, please let us know

Pay: $60,000.00 - $70,000.00 per year

Benefits:

• Paid time off

Application Question(s):

• Tell us about your experience supporting a CEO, founder, or senior executive. What were your main responsibilities?
• What AI tools do you use, and how have they helped you work more efficiently?
• Describe a time you had multiple urgent priorities. How did you decide what to handle first?
• What experience do you have with QuickBooks Online and handling confidential financial information?
• Are you comfortable being available for communication and responding within two hours on Saturdays and Sundays between 8:00 AM and 6:00 PM?
• Do you have a valid driver’s license, a reliable vehicle in good condition, and the ability to commute to the office every day?

Experience:

• QuickBooks online: 1 year (Required)
• Executive Assistant: 2 years (Required)

Work Location: In person

Salary : $60,000 - $70,000