He previously served as general counsel for an information technology firm in the healthcare industry. He represented that company in all aspects of bid protests and contract negotiations with the federal government and reviewed and executed contractual agreements. Matthew also developed policies and procedures for corporate compliance and federal cybersecurity requirements; managed proposals and reviewed proposals for compliance and advised on bid/no-bid decisions for solicitations; counseled executives on sensitive human resource matters; and advised on procurement regulations and strategies.

Prior to entering law school, he was a business communications consultant in Seoul, South Korea, for four years, working with high-level Korean executives.

During law school, he worked as a legal intern for the Honorable Judge Lydia Kay Griggsby of the U.S. Court of Federal Claims, a student attorney for the DC Law Students in Court legal clinic and a program manager at the Public Contracting Institute.