Robert R. Kaplan, Jr.

Robert R. Kaplan, Jr. serves as Chief Legal Officer and Executive Vice President, Corporate Development, for Red Oak Capital Holdings and its affiliate, Oak Real Estate Partners (OREP). A well-regarded expert in the federal JOBS Act, the veteran securities lawyer is also a pioneer and advocate in the revision and revitalization of SEC Regulation A.

As Chief Legal Officer, Rob develops and leads the corporate legal strategy for Red Oak and OREP; works with other executive management team members to formulate and maintain internal audits, corporate compliance programs and general management policies; and oversees delivery of legal services and resources to accomplish corporate goals, strategies and priorities. In his role as EVP for Corporate Development, Rob works with the companies’ CEO and Chief Strategy Officer to devise and execute capital markets strategy and long-term growth and development plans. He is based in the firm’s Charlotte, NC office.

Throughout his nearly 30-year career, Rob has completed more than $4 billion worth of securities transactions, institutional financings of real estate acquisitions and M&As. He is well-versed in the placement of alternative investments in the retail, independent broker-dealer and registered investment advisor market. His career also includes public sector experience, having served on the Virginia Board of Housing and Community Development.

Rob, who holds a Juris Doctor degree from the College of William & Mary’s Marshall-Wythe School of Law, has been recognized as a Best Lawyer in America within his fields each year since 2013. He was also named as the 2022 “Lawyer of the Year” by Best Lawyers® for leveraged buyouts and private equity law.