Charles Di Maggio

Chief Executive Officer

Mr. Di Maggio heads Greystone Management Solution’s leasing and asset management teams throughout the United States. Actively involved in real estate, management, law and construction in both the public and private sectors for over 35 years, Mr. Di Maggio provides our clients his broad experience in real estate law, lease negotiation, drafting, retail concession development, valuation and public sector procurement.

Prior to joining Greystone, Mr. Di Maggio was an executive vice president for Grenadier Realty Corp. He has also served as the City of New York’s lead housing and real estate lobbyist in Albany, the Assistant Commissioner for Local Government Affairs and Contract Management for the Department of Housing Preservation and Development, and as the Assistant Representative to the Board of Estimate for the Mayor’s Office of the City of New York under the administration of Edward I. Koch.

Mr. Di Maggio is a member of the American Public Transportation Association (APTA), where he is the founding co-chair of the Public Private Partnership Committee’s subcommittee on Real Estate and sits on the Business Member Board of Governors. Mr. Di Maggio is an adjunct professor at the Graduate School of Urban Planning at UMASS/Boston where he instructs a course on Urban Real Estate and Transit Oriented Development. He is a licensed Real Estate Broker in State of New York and Commonwealth of Pennsylvania, and a licensed attorney in the states of New York and Colorado.

Jaime Harris

Chief Operating Officer & Counsel

Ms. Harris oversees the division’s counsel staff in the drafting of Requests for Proposals, leases, licenses, disposition agreements, and other transaction documents for our public and private sector clients. During her tenure with Greystone Management Solutions, Ms. Harris has been integral in the development of all protocols and policies governing our work and the expansion of our services to clients across the country.

Prior to joining Greystone, Ms. Harris was in private practice where she focused on commercial litigation and transactional matters. She is a licensed Real Estate Broker in New York State and a licensed attorney in the states of New York and New Jersey. Ms. Harris is a member of the American Public Transportation Association (APTA), where she is a member of the Real Estate Committee.

Tom Cox

Managing Director

Mr. Cox has over 20 years of experience in real estate services in both corporate and governmental environments. He currently is Greystone’s Project Executive overseeing the management of the Massachusetts Bay Transportation Authority’s real estate portfolio; advising and facilitating real property dispositions, and supporting the agency by generating innovative solutions to increase non-fare box revenue.

Key accomplishments of Mr. Cox’s career include:

  • Renegotiation of the master lease for major inter-modal transit station in Massachusetts on behalf of public landlord, leading to a revenue increase of $152M
  • Responsibility for contract management of 9M square feet of real property across 12 states
  • Implementation of consolidated property platform for major bank across Europe, Middle East, and Africa
  • Managed municipal approvals process as Town Planner for the Hingham Shipyard mixed use development project

Mr. Cox is a noted expert in real estate dispositions, including sales, long-term lease negotiations, air rights, easements, and other complex transactions, as well as acquisitions.

Matthew Hunt

Senior Real Estate Advisor

Mr. Hunt has over 15 years’ experience in providing real estate advisory services to institutional clients throughout the world. In his capacity as a Senior Real Estate Advisor, Mr. Hunt advises clients on strategies for monetizing their real property assets, effectively managing their portfolio, and Transit-Oriented Development.

Mr. Hunt is an expert in strategy, establishment, and management of Public-Private Partnerships. Mr. Hunt has a deep understanding of all aspects of real estate development, including structuring agreements for development, financing, construction management, revenue sharing, property management, land disposition, and partnerships; having sat on both sides of the table for P3 transactions.

Notable accomplishments of Mr. Hunt’s career include:

  • Structured the financing for over $1B in real estate development, including bond and traditional debt financing
  • Served as chief real estate advisor to numerous municipalities, counties, federal agencies, and corporations, throughout the world
  • Served as chief negotiator in structuring of numerous construction management, development, revenue sharing, and land disposition agreements for clients on both public and private side of Public-Private Partnership transactions

Mr. Hunt earned an M.B.A. in Finance from Emory University and graduated magna cum laude from the University of Georgia. He is fluent in both the French and Czech languages.

Michael Plesnitzer

Managing Director

Mr. Plesnitzer serves as Greystone’s Project Executive overseeing the dedicated staff managing New Jersey Transit’s leased real estate portfolio. Mr. Plesnitzer manages the agency’s Request for Proposals process and leads efforts to increase non-fare box revenue.

Key accomplishments of Mr. Plesnitzer’s career include:

  • Successfully re-positioned Newark Penn Station, which brought nationally-known retail tenancies to a major historic rail station
  • Implementation of system-wide ATM program for New Jersey Transit
  • Development and implementation of agency-specific database for the tracking of lease key dates, inspections, rent amounts, and other details

Mr. Plesnitzer is a Certified Property Manager (CPM), as well as licensed New Jersey Real Estate Salesperson. He is a member of the International Business and Management Association as well as the Institute of Real Estate Management (IREM).

Dennis Wood

Assistant Director, Business Development

Mr. Wood leads Greystone’s business development and communications efforts, responsible for all external communications and marketing activities of the division. Mr. Wood’s responsibilities include overseeing Greystone Management Solutions’ web and social media presence, developing all client-facing reports and proposals, and maintaining the division’s presence in the marketplace.

Prior to joining Greystone, Mr. Wood worked in property management. He holds a Bachelor of Business Administration in Finance & Real Estate from Temple University, and is a member of the American Public Transportation Associations’ Innovative Funding, Finance, and P3 Committee and its Real Estate Subcommittee.

Laura Kaplan

Senior Counsel

Ms. Kaplan is Senior Counsel in Greystone’s Massachusetts office, where she consults to the Massachusetts Bay Transportation Authority (MBTA) and the Massachusetts Department of Transportation (MassDOT) on all aspects pertaining to the disposition of surplus real property. In this role, Ms. Kaplan negotiates purchase and sale agreements, development agreements, leases, licenses and conveyancing documents. She also ensures procurement law compliance and prepares public offering documents.

Prior to joining Greystone, Ms. Kaplan was in private practice where she represented real estate developers and lenders on development, financing, lease, sale and acquisition transactions. Ms. Kaplan is a licensed attorney and Real Estate Broker in Massachusetts.

Ashleigh Coughlan

Managing Director

Ms. Coughlan, an experienced financial analyst, has direct experience working with public agencies and private sector commercial and residential clients providing financial analysis of management, lending and acquisition transactions. She currently provides analysis and reconciliation of complex commercial leases, augmenting her experience in many areas of real estate including asset management, lending and acquisitions. She assists our accounting team with the review or financial statements ensuring compliance with complex real estate leases, produces ad hoc reports, and develops Excel models for complex real estate agreements to illustrate compensation and revenue structures.

Notable accomplishments of Ms. Coughlan’s career include:

  • Implementation of a major revenue recovery initiative related to public permits and licenses
  • Management of the team servicing over 220 public parking facilities in New York and New Jersey
  • Oversight of billing activities for over 4,000 lease accounts in client’s portfolio
  • Provided support to management team of a multi-million-dollar loan program including Fannie Mae, Freddie Mac, CMBS and FHA loans

Ms. Coughlan earned her Master’s in Finance at the Dublin Institute of Technology and her Bachelors in Business and Accounting at the Galway Mayo Institute in Ireland. Ms. Coughlan is a member of the Irish Business Organization of New York.

Melissa Chaput

Broker & Senior Asset Manager

Ms. Chaput has over 18 years of asset management and brokerage experience concentrated in asset stabilization, financial analysis, and construction management; as well as public-sector procurement practices and lease negotiation. For our clients in Massachusetts, Ms. Chaput manages several multi-tenanted buildings and specializes in developing strategies for owned real estate assets and new asset initiatives that maximize return for clients. Her other responsibilities include brokerage, project oversight, accounting and expense reduction initiatives.

Notable accomplishments of Ms. Chaput’s career include:

  • Disposition of $105M in real estate assets across 14 states
  • Development and oversight of fuel service procurement; netting an additional $18 million dollars of new revenue for the Massachusetts Department of Transportation
  • Stabilization of defaulted and nonperforming travel service plazas, including curing of deferred maintenance and code issues
  • Advisor to construction team for 7,845 SF inter-modal mixed-use building in Hingham, MA

Ms. Chaput is a licensed real estate broker in the Commonwealths of Massachusetts and Virginia and the State of New Hampshire; and member of The Institute for Real Estate Management (IREM), the Urban Land Institute (ULI) and the American Public Transportation Association (APTA) where she is a member of its Real Estate Committee.

Andrew Knowlton

Director of Accounting

Mr. Knowlton is the Director of Accounting in Greystone’s Massachusetts office. His team is responsible for performing billing, collection, and reporting on behalf of the Massachusetts Bay Transportation Authority, including daily and monthly cash management, producing monthly financial reports detailing all real estate activity for the period. He serves as the System Administrator for treasury, accounting, and tenant management platforms.

Mr. Knowlton’s team was responsible for reconciling and collecting over $3M in past due funds for the MBTA while maintaining a 97% collection rate. Through this reconciliation process the MBTA has realized a 20% increase in recurring revenue since 2014. In addition to accounting duties, Mr. Knowlton is also responsible for overseeing the MBTA’s short term licensing program which has seen an increase in revenues of 55%.