Meet the Expert

Matthew Oakes

Matthew was appointed President of Real Estate Services in April of 2023 after 6 years with OSG. In this role, he leads all aspects of the Real Estate Services division, including sales, customer service, partner relationships and revenue growth, with a focus on driving innovation and delivering superior client experiences. Matthew’s executive leadership experience includes previously held positions as Chairman of the Board, CEO & President for both private and public software and eCommerce companies including Paybox Corp, Direct Insite Corp, Direct Media Networks, Mall Net Media Corp., and Westinghouse. His diverse background spans corporate strategy, operations, legal, and financial management, positioning him to drive growth and operational excellence in his current role. Matthew holds a B.S. Degree in Business Finance and Management from Cornell University, and Juris Doctor of Law from Nova Southeastern University. Matthew is a veteran having served in the United States Marine Corps for six years attaining the rank of Sergeant. He was deployed with the 3rd Marine Division serving multiple tours overseas as a Scout Sniper, and at Parris Island, SC as a Drill Instructor with the 1st Recruit Training Battalion.

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