Assistant Vice President, Investments

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Middleburg is a vertically integrated real estate investment, development, and construction firm specializing in rental housing across the United States since 2004.

Middleburg is seeking a diligent and resourceful leader capable of taking direct ownership over underwriting reliability, capital relationships, and transaction execution. The position requires daily collaboration with Land Acquisitions, Development, Asset Management, Construction, Research, and Property Management, and the ability to synthesize complex financial and development risks into clear, persuasive narratives for investors, lenders, and internal decision makers. This is a full‑time, in‑person role located at the Vienna, VA headquarters with frequent business travel.

• Accountable for underwriting conclusions and recommendations presented to the Investment Committee, including clear articulation of opportunities, downside risks, mitigation strategies, and conviction level.
• Oversee the work product of Associates and Analysts to produce reliable and accurate underwriting.
• Oversee the creation and maintenance of tools, policies, and procedures to ensure best‑in‑class underwriting and due diligence standards.
• Organize and distribute investor feedback received during ongoing marketing efforts to inform pipeline pursuit.

• Oversee the work product of Associates and Analysts to ensure best‑in‑class offering memorandums and supplemental marketing materials for investor/lender presentations and meetings.
• Pitch deals to and conduct tours with investors/lenders (alongside Development Lead).
• Manage equity and debt marketing lists, maintaining meticulous notes regarding feedback, approval status, and outstanding diligence questions.
• Facilitate investor/lender diligence by proactively managing data rooms and responding to questions in a timely manner.
• Prospect new capital relationships and maintain valuable existing relationships.

• Negotiate equity and debt term sheets, org docs, and loan docs with oversight and approval from Managing Director.
• Draft Investment Committee memos detailing proposed capital structures.

• Take accountability and extreme ownership of transaction execution, with authority to proactively drive timelines, elevate issues, and coordinate cross‑functional collaboration.

Accountable for the timeliness and accuracy of various reporting requirements including:

• Quarterly Internal Valuations
• GP Fund Investor Reporting
• Portfolio Management Reporting
• Market Insights Reporting (e.g., Sale Comps)

• Ideal candidates progressed from rigorous underwriting roles into capital markets or principal‑side execution positions, with at least 7 years’ experience.
• Proven track record of sourcing capital and leading transaction closings.
• Expert underwriting capabilities and proficiency in MS Excel.
• Excellent verbal and written communication skills.
• Bachelor’s degree in a related subject.
• Willingness to work in office full‑time.
• Willingness to travel frequently as directed by Managing Director.

• Great benefits – comprehensive health, dental, vision, paid time off, volunteer time, company‑paid holidays, 401(k) match, employer‑paid life and AD&D insurance, and educational reimbursement.
• A challenging job that promotes excellence, knowledge, service, and integrity. Team members provide top‑notch customer service exceeding expectations.
• Great culture – responsible leadership, initiative, respect, empathy, and a supportive environment where we build better communities one unit at a time.

Who is Middleburg Communities?

At Middleburg Communities, we share a vision for greater value creation through community impact. Our success is rooted in a genuine desire to serve local communities thoughtfully and holistically. By enhancing lives we contribute positively to neighborhoods and maximize real returns for our partners.

Middleburg is a fully integrated real‑estate investment, development, and construction firm focused on rental housing in high‑growth markets across the southeastern United States. Since 2004, the company has acquired and developed over 22,000 apartment units, executed approximately $3 billion in transactions, and amassed about $1 billion in recurring annual development value.

Middleburg Communities is an equal‑opportunity employer committed to diversity and inclusion. We welcome qualified applicants from a variety of backgrounds, including race, color, religion, sexual orientation, gender, gender identity, expression, genetic information, national origin, age, disability, or status as a disabled or Vietnam‑era veteran.