Barbara Matthews joined Commonwealth Capital in 2024 as Executive Director, Capital Markets, bringing an extensive track record of legal and strategic leadership across diverse corporate structures, including public, private, private equity, and family-owned businesses. She is a seasoned legal executive and trusted advisor to senior leaders and boards of directors, with expertise in navigating complex legal and regulatory landscapes, particularly in mergers and acquisitions (M&A), growth capital transactions, initial public offerings (IPOs), and ownership succession planning. Mrs. Matthews has a proven ability to design and implement robust internal controls and governance frameworks that are instrumental in preparing companies for investor scrutiny and public company compliance.

Prior to her role at Commonwealth Capital, Barbara served for 16 years as Senior Vice President, General Counsel, and Corporate Secretary at Hagerty, the world's largest provider of specialty insurance for classic cars, where she was instrumental in the company’s transformation from a family-owned business to a publicly traded entity. She led the development of Hagerty’s first independent board of directors and played a pivotal role in the company’s successful listing on the New York Stock Exchange (NYSE). Her leadership in governance practices and public company readiness has earned her a reputation as an authority in these fields.

Barbara’s career includes chief legal executive roles at four major enterprises: Hagerty, Priority Solutions, Heller Financial, and Sears Savings Bank. She has overseen notable M&A transactions, such as the acquisition of a $700 million equipment leasing business, a start-up ride-sharing company, and a digital motorsport business. Additionally, she has managed significant capital transactions, including real estate sale-leaseback agreements, IPOs, tender offers, SPAC mergers, and a $200 million growth capital investment.

Her strategic expertise extends to forging and managing complex joint ventures with leading global banks and financial institutions, facilitating market entries across multiple continents. She has also led legal, compliance, risk, and governance teams on domestic and international scales in highly regulated industries such as banking, corporate finance, insurance, and logistics. With extensive experience in government relations, Barbara has successfully navigated legislative advocacy, policy development, and regulatory challenges across jurisdictions in the United States, Canada, Latin America, and Asia.

In addition to her executive leadership, Barbara contributes to governance as a board member for Gray & Company, Inc., Chairman of the Board for the Elk Rapids Downtown Development Authority, and as a board member of the Grand Traverse Regional Community Foundation. Her governance experience includes serving on Finance, Risk Management, and Nominating & Governance Committees, as well as prior roles as a board director and secretary for a Bermuda-based insurance company and a start-up sustainable shoe company.

At Commonwealth Capital, Barbara serves as a member of the Senior Management Team, where she manages the company’s investment banking and broker-dealer capital market relationships. Reporting directly to the President, she is responsible for formulating and executing the company’s Blue Chip Program™ capital source engagements, ensuring alignment with strategic objectives and corporate standards. She also plays a key role in creating, updating, and overseeing the compliance of corporate finance operating policies and procedures for Executive Board approval and implementation.

Mrs. Matthews further serves on the Investment Policy Committee of Commonwealth Capital Income Fund-I.

Barbara earned her Juris Doctor (J.D.) from DePaul University College of Law. She holds a NACD
Directorship Certification and a certificate in Private Company Governance from the Private Directors Association.