Jonathan Oakman is a visionary real estate executive and community development strategist whose career has bridged the complex worlds of public policy, commercial real estate, and mission-driven urban revitalization. As Vice President of Development at Landmark Enterprises, he brings a rare combination of analytical precision, creative problem-solving, and deep civic engagement to every project he leads.
Jonathan’s current portfolio includes a dynamic mix of commercial initiatives—a pair of Class A build-to-suits for major industrial clients, a standalone emergency department for a physician-led group, and the adaptive reuse of a historic jail property, each showcasing his deftness in managing projects from predevelopment through lease-up. As a key member of Landmark’s leadership team, he also contributes to enterprise-level strategy across finance, legal, HR, and operational decisions, reinforcing his value not only as a developer but as a strategic executive leader.
Prior to stepping into his current role, Jonathan held a series of pivotal positions at Landmark, first as Development Manager and then as Vice President. Over these years, he negotiated complex deals with development and capital partners, public agencies, and lenders. Notably, he oversaw the delivery of multiple Class A industrial developments and a signature 60,000-square-foot office project—each completed with financial discipline and architectural integrity.
Jonathan’s entrepreneurial spirit took shape at Hanlan Consulting & Development, where as Vice President he helped launch and steer a full-service commercial real estate startup. His leadership extended from sourcing Charleston-area development opportunities to advancing projects through the entitlement process. This experience sharpened his fluency in deal structuring and partner collaboration—skills he first developed as Co-Founder and Principal of The Persimmon Group, a tax credit consultancy advising on New Markets Tax Credit (NMTC) transactions and adaptive reuse efforts.
Before turning his focus fully to private-sector development, Jonathan served in key roles for the City of Charleston and the NYC Department of Housing Preservation and Development. In Charleston, he was instrumental in structuring the financing for a $142 million community development project, leveraging public and philanthropic resources in support of a transformational redevelopment. He also created the Charleston Redevelopment Fund, a nonprofit CDE that sought NMTC allocations and supported developers with technical underwriting and advisory services.
Earlier in his career, Jonathan contributed to New York City’s affordable housing ecosystem, helping direct a $130 million annual budget for the City’s Multi-Family New Construction Program. He underwrote and closed dozens of development loans and helped shape large-scale mixed-use projects, gaining invaluable experience in navigating municipal finance and land use planning.
Jonathan’s academic foundation is as strong as his professional trajectory. He earned a Master’s in Public Affairs from Princeton University’s Woodrow Wilson School, where he focused on economic analysis and project management, and graduated magna cum laude with Honors in Political Science from Williams College. He has also pursued specialized coursework in real estate finance at NYU’s Real Estate Institute. His editorial work on New Downtowns: The Future of Urban Centers (2006) further reflects his longstanding interest in sustainable urbanism.
Beyond the boardroom, Jonathan is a dedicated civic participant and creative spirit. He serves on the board of the Charleston Redevelopment Corporation, chairing its Acquisition & Development Committee, and has held a 13-year tenure as Secretary of the Redux Contemporary Art Center board. A member of the Urban Land Institute, Jonathan also nurtures his personal passions through watercolor painting, guitar, and the occasional ultimate frisbee match—pursuits that reveal the same energy and balance he brings to his professional life.
Jonathan Oakman’s career stands as a testament to the powerful synergy of private investment and public purpose. With an expansive portfolio, proven leadership, and an enduring commitment to thoughtful development, he continues to shape communities in ways that are both economically sound and socially impactful.
Character
Jonathan Oakman demonstrates exceptional integrity, dedication, and civic-mindedness throughout his career, consistently aligning real estate development with community impact and public benefit. His ability to lead with authenticity and purpose has earned him trust across both public and private sectors.
Knowledge
With advanced academic training from Princeton and Williams College, as well as hands-on experience in tax credit finance, urban policy, and commercial development, Jonathan possesses a deep and nuanced understanding of real estate, public-private partnerships, and economic development.
Strategic
Jonathan is a forward-thinking leader who integrates financial acumen, stakeholder collaboration, and long-term planning to drive transformative development projects. His approach consistently balances business goals with broader community revitalization strategies.
Communication
An articulate and persuasive communicator, Jonathan effectively engages with partners, public officials, investors, and community stakeholders to build consensus and advance complex initiatives. His ability to translate technical concepts into shared vision is key to his leadership success.
