Matthew Webster is Senior Vice President, Chief Credit Officer at Red Oak Capital Holdings, LLC where he leads the firm’s credit culture, lending operations, and risk management initiatives. Based in the firm’s Charlotte, North Carolina headquarters, Matt oversees all loan portfolios and directs the underwriting, loan operations, and asset management teams to ensure disciplined credit decision-making and strategic portfolio management. He plays a key role in structuring and pricing Red Oak’s investments on a risk-adjusted basis while working closely with origination personnel to maintain a strong lending pipeline.
In addition to his responsibilities at Red Oak, Matt leads credit oversight at Oak Real Estate Partners (OREP), where he manages credit policies, risk assessment, and underwriting operations for the firm’s institutional investment strategies. His broad oversight ensures an integrated approach to credit and capital deployment. Matt will also sit on both companies’ Credit and Investment Committees.
With more than 30 years of experience in commercial real estate finance, alternative asset management, and capital markets, Matt has been involved in structuring and executing more than $250 billion in transactions across senior and mezzanine finance, equity investment, non-performing loan management, and property development. Throughout his career, he has worked with sovereign wealth funds, REITs, institutional asset managers, and private capital sources.
Prior to joining Red Oak, Matt served as Global Head of Real Estate Finance for HSBC, where he oversaw more than $100 billion in global commercial real estate exposure. His career also includes leadership roles at Morgan Stanley, Goldman Sachs, Hypo Real Estate, and FitchRatings, where he advised governments, central banks, and industry regulators on financial stability and risk management.
Matt holds a Chartered Financial Analyst (CFA) certificate and earned dual bachelor’s degrees in Business Management and Economics from North Carolina State University. He has served in various industry and regulatory advisory roles and is a frequent guest lecturer on commercial real estate finance.
Thomas A. McGovern is Chief Financial Officer of Red Oak Capital Holdings, where he applies his strategic and tactical capabilities to help drive the firm’s continued enterprise growth. Based in Charlotte, North Carolina, the multifunctional executive leads the national commercial real estate finance company’s financial accounting and reporting, investor communications, and ERP systems requisition efforts.
Thomas’ capital markets track record spans more than two decades of working with companies and sponsors to effect private placements, high yield and investment-grade debt issuance, IPOs, and follow-on equity offerings. He has served as an Investment Banker and Equity Research Analyst for financial services firms including Morgan Stanley, Cypress Associates, RBC Capital Markets and, most recently, Nomura. As Executive Director, he executed $14 billion in high-yield financing and led the firm’s insurance services coverage and private equity sponsor relationship efforts.
Thomas earned a master’s degree in business administration from Charlottesville, VA’s Darden Graduate School of Business at the University of Virginia and is a summa cum laude graduate of Hamilton College with a degree in economics. A Certified Public Accountant, he also holds a Chartered Financial Analyst designation and a Series 79 securities license from the Financial Industry Regulatory Authority (FINRA).
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.
Paul Cleary is President and Chief Operating Officer of Red Oak Capital Holdings, where he oversees the firm’s finances, business partnerships and funding opportunities. The Charlotte, North Carolina-based executive is also charged with overseeing and measuring the success of business and employee initiatives for the national commercial real estate finance company.
In addition to his role with Red Oak, Paul serves as Managing Partner and President of Oak Real Estate Partners (OREP), a national fund manager focused on the institutional investment sector.
Paul has over 25 years of national commercial real estate lending experience involving small-balance originations, construction loans and federally chartered credit union portfolios. He has significant expertise in creating and managing lending policies and guidelines, as well as the development of operational tools and information systems to support financing operations. Before Red Oak, Paul was a Senior Loan Originator with Parkview Financial, and served as Chief Operating Officer for Money360, Inc.
Paul is an alumnus of the University of California, Santa Barbara, where he earned a bachelor’s degree in political science. He also holds a master’s degree in business administration from the University of California, Irvine, as well as a Juris Doctor degree from the University of San Diego School of Law.
Kevin P. Kennedy is a Managing Principal and Chief Sales and Distribution officer with Red Oak Capital Holdings, responsible for capital acquisition, platform distribution and broker dealer-relationships for the firm’s offerings. He has been with the commercial real estate finance firm since its inception in 2016 and is based in the Detroit, Michigan area.
Kevin has a long history in sales and leadership roles within the investment and asset management industry. Before Red Oak, he spent 26 years at BlackRock, where he was most recently a Managing Director and Divisional Sales Director. In this role, he led a team that marketed and sold BlackRock’s active, passive and alternative investments across a 22-state area. Kevin also spent the first decade of his career with Merrill Lynch Investment Managers, last serving as a Director and Vice President in the Midwest.
A graduate of Pittsburgh’s Duquesne University, Kevin holds Series 7, 24, 63, 65 and 66 licenses from the Financial Industry Regulatory Authority (FINRA). He received a Certified Investment Management Analyst certification (CIMA) designation from Wharton Executive Education-University of Pennsylvania in 2007.
Raymond T. Davis is President & Chief Strategy Officer of Red Oak Capital Holdings and its affiliate, Oak Real Estate Partners (OREP). Operating out of Detroit, Michigan, he is charged with developing, communicating, and sustaining the companies’ medium- and long-term strategic initiatives including fund formation, AUM strategy, M&A opportunities, and the development of future business lines.
Over the course of his 25-year career, Ray has gained significant expertise in capital markets, corporate growth and strategic initiatives while working with family office pension funds and institutional clients.
A seasoned commercial real estate capital markets professional, Ray previously served as a Managing Principal and Corporate Forensics Advisory Consultant for Archon Capital LP. He also co-founded JADDA Capital Management, where he led origination and portfolio diversification efforts for the investment platform.
Ray, who studied business and economics at Wayne State University, holds a Series 22 license and Central Registration Depository (CRD) registration from the Financial Industry Regulatory Authority (FINRA).
Gary Bechtel is Chief Executive Officer & Managing Principal of Red Oak Capital Holdings, responsible for managing the national commercial real estate finance firm’s lending operations and business development efforts. He operates out of the firm’s Grand Rapids, Michigan office.
In addition to his duties with Red Oak, Gary heads the investment management leadership team for Oak Real Estate Partners. As Managing Principal and CEO, he has direct oversight of all loan portfolios and operations for the firm, a national, multi-fund manager focused on the institutional investment sector.
Over the course of his nearly 40-year career, Gary has been involved in the origination, underwriting, structuring, placement and closing of more than $10 billion in commercial debt transactions, utilizing various financing structures including permanent, bridge, equity, mezzanine, and construction loans.
Gary has held multiple leadership roles with both lenders and intermediaries throughout his career. He joined Red Oak and OREP after serving as President of Money360, where he directed and executed the firm’s expansion strategy and sat on its Credit Committee and Board of Directors. Prior to that, he was Chief Lending and Originations Officer of CU Business Partners, LLC, a major national credit union service organization, preceded by positions with such companies as Grubb & Ellis, Meridian Capital, Johnson Capital and FINOVA Realty Capital.
Gary attended the University of California, San Diego, majoring in economics. He currently sits on the Executive Board of the California Bankers Association and has been a longtime member of the Mortgage Bankers Association of America (MBA), National Association of Industrial and Office Properties (NAIOP), and International Council of Shopping Centers (ICSC). Gary has been a featured moderator/speaker at numerous industry events and is a frequent contributor to several regional and national publications.