Executive Operations Assistant Jobs in Maryland (NOW HIRING)

Are you the kind of person who thrives on being the trusted right hand behind a growing business?

Do you enjoy bringing order to chaos, anticipating needs before they arise, and helping ambitious leaders execute at a high level?

This is a full-time, primarily home-based role requiring consistent engagement during core business hours and limited after-hours monitoring when time-sensitive matters arise.

The Josh Shapiro Team at Douglas Realty is seeking an Executive Operations Manager to serve as a strategic and operational partner to the Team Leader with the real estate business as the primary focus and secondary support across several business-minded ventures. The right person will be highly organized, proactive, adaptable, and energized by supporting multiple moving pieces while helping drive projects forward.

If you’re looking for a role where you can make a significant impact, take ownership, and grow alongside a driven forward-thinker, we’d love to hear from you.

This is a high-impact, primarily home-based role that combines executive support, operations coordination, project management, and client-facing responsibilities. You’ll help keep the business running smoothly behind the scenes while also stepping into situations that require communication, leadership, and follow-through.

The ideal candidate understands that supporting a forward-thinker means balancing structure with flexibility. Priorities may shift, new opportunities may emerge, and no two weeks will look exactly the same.

Compensation

• Base Salary: $70,000–$80,000

• Expected Earnings: Approximately $80,000–$95,000 annually

• Hybrid Work Opportunity

• Location: Anne Arundel County, Maryland

• Opportunity to grow into a Director of Operations role with a successful real estate and forward-thinking organization

$70,000 - $80,000 Base Salary

Executive & Operational Support

• Manage multiple business email accounts, calendars, scheduling, priorities, and day-to-day operational coordination for the Team Leader

• Triage incoming communications and determine what can be handled independently, what should be drafted for review, and what requires the owner’s direct involvement.

•  Oversee administrative systems, workflows, and internal processes to keep the business running smoothly

• Prepare meeting agendas, document action items, and ensure timely follow-through

• Coordinate and help lead team meetings, including tracking accountability and next steps

• Anticipate needs, identify gaps, and proactively solve problems before they escalate

• Provide local in-person operational support including property visits, signage, vendor coordination, meetings, and occasional business errands

Real Estate Operations & Administrative Support

• Coordinate real estate transactions, listings, and related documentation, escalating negotiation matters

• Maintain CRM records, databases, and communication follow-up systems

• Prepare and organize contracts, forms, disclosures, and other real estate administrative materials as needed

• Track deadlines, inspections, vendor appointments, and transaction milestones

• Manage listing coordination, social media, website, and marketing execution, including signage and property-related logistics

•  Ensure day-to-day real estate operations remain organized, responsive, and client-focused

Client & Team Coordination

• Serve as a professional point of contact for clients, vendors, contractors, tenants, and business partners

• Provide a high level of responsiveness and customer service across all interactions

• Coordinate communication between the Team Leader and internal or external stakeholders and, over time, train current and new agents on team systems

•  Help create a seamless experience for clients and partners throughout every stage of the process

Rental Properties and Construction Support

• Communicate with tenants regarding routine questions, repairs and property-related concerns.

• Coordinate contractors, obtain estimates, schedule work, and confirm that repairs have been completed properly.

• Assist with tenant showings, property visits, inspections and turnover-related tasks.

• Track open rental-property issues and ensure they are resolved without repeated owner involvement.

• Assist with scheduling, vendor communication, documentation, and follow-up for residential construction projects.

• Visit properties or meet contractors locally when an in-person presence is needed.

• Gradually assume authority to approve routine repairs and operating expenses within established financial limits.

Business-Minded Project Assistance

• Support special projects and new business initiatives as they develop

• Conduct research, gather information, and organize recommendations for decision-making

• Assist with implementation of operational, marketing, and business development initiatives

• Adapt quickly to new opportunities, priorities, and projects as the organization grows

What Makes This Opportunity Different

This role is designed for someone who wants to serve at a high level and become a genuine right-hand partner.

Because the business includes real estate operations, rental properties, construction projects, and ventures, priorities can occasionally shift and no two weeks will look exactly the same. Success in this role requires someone who:

• Is comfortable working in a dynamic and occasionally unpredictable business

• Takes initiative rather than waiting for detailed instructions

• Thinks two steps ahead and proactively solves problems

• Owns outcomes, keeps commitments, and communicates before deadlines are missed

• Can confidently interact with clients, vendors, contractors, and team members

•  Is willing to assist with local errands, signage, property visits, and other in-person support tasks

You’ll likely be a great fit if you:

• Have meaningful experience in either real estate operations or serving as the trusted right-hand to a business owner or executive

• Are exceptionally organized and detail-oriented

• Communicate professionally and confidently in both written and verbal interactions

• Can balance behind-the-scenes administrative work with client-facing responsibilities

• Enjoy both strategic coordination and rolling up your sleeves to get things done

• Are comfortable leading meetings, following up with others, and driving accountability

• Live locally in Anne Arundel County, Maryland and are available for regular in-person support

• Hold an active Maryland real estate license or are willing to obtain one within an agreed-upon timeframe after hire

Preferred Experience

• Experience spanning both real estate operations and executive or forward-thinking support

• Property management or rental coordination

• Construction or project coordination

• Operations management or project management responsibilities

• Working in a fast-paced environment

The Josh Shapiro Team at Douglas Realty is a high-performing real estate team serving clients throughout Anne Arundel County and the surrounding Maryland area. Known for delivering exceptional client service and strong results, the team has built a reputation for professionalism, responsiveness, and a commitment to helping clients navigate one of life’s biggest decisions with confidence.