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
Compensation:
$70,000 - $80,000 Base Salary
Responsibilities:
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
Qualifications:
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
About Company
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.
