Vincent M. Holloway

Vincent M. Holloway is an attorney and senior technology executive with three decades of experience at the operational core of the federal acquisition and defense IT enterprise. He counsels federal contractors on government contract disputes and investigations, regulatory compliance, and cybersecurity and technology law — practice areas in which his government service, active clearance, and executive experience provide contextual depth that generalist counsel cannot match.

Holloway holds active bar admissions in the District of Columbia and Kentucky, maintains an active Top Secret security clearance, and provides virtual general counsel services with authority to represent clients before most federal agencies and adverse parties.

His government contract and investigations practice is grounded in five years as Assistant Inspector General for Investigations at the Defense Information Systems Agency (DISA), where he directed more than 500 criminal, administrative, and government contract investigations. He personally oversaw DISA's largest criminal investigation, resulting in the Department of Justice's successful prosecution of individuals and entities responsible for fraudulent government contracts. He also investigated source selections, bid protests, and contract administration matters, coordinating with DOJ, the FBI, and the Department of Labor. Subsequent executive advisory roles provided direct experience structuring prime and subcontract agreements on task orders valued up to $249 million, including contract modifications, equitable adjustments, and change orders on complex multi-year vehicles.

His regulatory compliance practice draws on direct engagement with FAR, DFARS, and Titles 10, 40, 44, and 50 of the United States Code, through which he developed and delivered DoD-level policy and doctrine on IT management and acquisition. He has advised senior officials across the C5ISR community — including USSTRATCOM, the Missile Defense Agency, and multiple Program Executive Offices — and his experience designing and implementing agency-wide investigative policies at DISA directly informs his counsel on internal governance program development, compliance program design, and organizational risk management.

Holloway's cybersecurity and technology practice is built on hands-on technical experience. As a U.S. Army Signal Officer and later a senior defense technical advisor, he developed and acquired cryptographic systems, key management infrastructure, and network initialization data products used across DoD enterprise and tactical systems. He has directed computer network defense initiatives, managed classified and unclassified network operations, and led operational testing of advanced communications and satellite systems — a foundation that allows him to engage client engineering and program management teams on cybersecurity compliance, CMMC readiness, and technology acquisition matters.

In private practice, Holloway has counseled clients ranging from individuals and small businesses to Fortune 500 corporations — representing clients in federal agency employment discrimination and prohibited personnel practices proceedings; advising on workforce classification, independent contractor arrangements, and confidentiality agreements; and counseling growing businesses on entity formation, operational governance, and strategic risk management.