Senior Executive Assistant & Real Estate Operations Manager

Job Description

Job Description

Position Overview

Chesapeake Companies is seeking an exceptional Senior Executive Assistant & Real Estate Operations Specialist to serve as a trusted partner to the Chief Executive Officer across a growing portfolio of real estate investments, development projects, commercial properties, residential properties and operating businesses.

This is not a traditional Executive Assistant position. While executive support is an important component of the role, the primary focus is helping manage and coordinate real estate acquisitions, dispositions, financing activities, leasing initiatives, development projects, and property management operations.

The ideal candidate is highly organized, proactive, detail-oriented, and capable of managing multiple priorities simultaneously. This individual will serve as the central point of coordination between the CEO, attorneys, lenders, title companies, brokers, property managers, contractors, consultants, and other stakeholders to ensure projects continue moving forward and critical deadlines are met.

The successful candidate will thrive in a fast-paced entrepreneurial environment, possess strong business acumen, and have prior experience in real estate, property management, development, construction, lending, legal support, or transaction coordination.

 

Benefits & Compensation

• Competitive salary based on experience
• Performance-based bonus opportunities
• 100% employer-paid employee health insurance
• Dental, vision, life, and disability insurance
• 401(k) retirement plan
• Tuition reimbursement for approved educational programs
• Monthly gym membership reimbursement
• Paid time off and holidays
• Professional development opportunities

 

Executive Support Responsibilities

• Manage and prioritize the CEO's calendar, meetings, travel, and appointments.
• Manage executive email communications, ensuring urgent matters receive immediate attention.
• Draft professional correspondence, reports, presentations, and executive communications on behalf of the CEO.
• Track action items, deadlines, and follow-up responsibilities resulting from meetings and business discussions.
• Assist with strategic initiatives and special projects across multiple business entities.
• Prepare executive briefing materials and decision-support documents.
• Serve as a trusted gatekeeper and extension of the CEO.

 

Real Estate Operations, Acquisitions & Transaction Management

This position plays a critical role in supporting the CEO's real estate activities and ensuring transactions, projects, and property operations remain organized and moving forward.

 

Responsibilities Include:

• Coordinate real estate acquisitions and dispositions from contract through settlement and closing.
• Manage transaction timelines, due diligence requirements, financing milestones, contingency deadlines, and closing deliverables.
• Serve as the primary coordinator between attorneys, lenders, bankers, title companies, brokers, engineers, surveyors, contractors, and consultants.
• Organize and track documentation required for construction loans, refinancing transactions, acquisitions, and property sales.
• Monitor outstanding lender requests, legal requirements, title matters, insurance requirements, and settlement conditions.
• Review contracts, leases, purchase agreements, loan documents, settlement statements, and related real estate documentation to identify deadlines, action items, and follow-up requirements.
• Assist with leasing activities, lease administration, and lease-related communications.
• Support property management operations by coordinating with property managers, tracking tenant issues, maintenance matters, vendor activities, and operational priorities.
• Maintain organized records of contracts, leases, loan documents, property files, entity records, permits, insurance policies, and transaction documentation.
• Conduct research regarding property values, comparable sales, development opportunities, and investment opportunities.
• Create and maintain project trackers to ensure no deadlines, deliverables, approvals, or critical tasks are missed.
• Drive accountability among stakeholders by proactively following up on outstanding items and ensuring projects continue moving toward completion.
• Provide regular status updates to the CEO regarding acquisitions, financing activities, leasing initiatives, development projects, and property operations.

 

Project Management & Organization

• Manage multiple active projects simultaneously while maintaining exceptional attention to detail.
• Prioritize competing tasks and ensure high-priority initiatives receive timely attention.
• Develop and maintain systems that improve organization, communication, and operational efficiency.
• Track project milestones, deadlines, deliverables, and stakeholder responsibilities.
• Ensure projects remain on schedule and stakeholders remain accountable.

 

 

Qualifications

 

Required Experience

• 5+ years of experience supporting senior executives, business owners, developers, investors, or leadership teams.
• Experience in commercial real estate, property management, real estate development, construction, lending, title/settlement services, legal support, or transaction coordination.
• Experience coordinating multiple projects involving attorneys, lenders, brokers, contractors, consultants, and external stakeholders.
• Demonstrated ability to manage competing priorities and complex workflows.
• Strong experience with Microsoft Office Suite, including Outlook, Excel, Word, and PowerPoint.

 

Preferred Experience

• Commercial real estate transactions
• Property management
• Real estate development
• Construction lending
• Commercial leasing
• Real estate investment operations
• Title, escrow, or settlement coordination
• Real estate legal support or paralegal experience

 

Skills & Competencies

• Exceptional organizational skills and attention to detail.
• Ability to manage large volumes of information and documentation.
• Strong project management and follow-through capabilities.
• Excellent written and verbal communication skills.
• Ability to read, understand, and organize contracts, leases, loan documents, and transaction-related materials.
• Strong problem-solving and critical-thinking abilities.
• Ability to work independently and proactively.
• Professional judgment and discretion when handling confidential information.
• Comfortable operating in a fast-paced, entrepreneurial environment.

 

What Success Looks Like

The ideal candidate becomes an indispensable partner to the CEO by creating organization, accountability, and follow-through across real estate transactions, development projects, property operations, and executive priorities.

This individual ensures acquisitions close on time, lender requirements are satisfied, projects continue moving forward, stakeholders remain accountable, and critical tasks never fall through the cracks.

Company Description

We are a growing real estate investment and property management company focused on the acquisition, ownership, and management of a diverse portfolio of residential and commercial properties. Our organization is actively involved in identifying new investment opportunities, improving existing assets, and delivering high-quality property management services across multiple markets.

With a hands-on and growth-oriented approach, we oversee all aspects of property operations, including acquisitions, tenant relations, maintenance coordination, leasing, financial performance, and long-term asset planning. Our team values professionalism, accountability, and operational excellence while fostering a collaborative and fast-paced work environment.

As we continue to expand our portfolio, we are seeking motivated professionals who are eager to contribute to a dynamic company with long-term growth opportunities.

Company Description

We are a growing real estate investment and property management company focused on the acquisition, ownership, and management of a diverse portfolio of residential and commercial properties. Our organization is actively involved in identifying new investment opportunities, improving existing assets, and delivering high-quality property management services across multiple markets.\r\n\r\nWith a hands-on and growth-oriented approach, we oversee all aspects of property operations, including acquisitions, tenant relations, maintenance coordination, leasing, financial performance, and long-term asset planning. Our team values professionalism, accountability, and operational excellence while fostering a collaborative and fast-paced work environment.\r\n\r\nAs we continue to expand our portfolio, we are seeking motivated professionals who are eager to contribute to a dynamic company with long-term growth opportunities.