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Gregory Cherundolo has an extensive and diverse work experience. Gregory started their career in 1992 as a County Detective at the Lackawanna County District Attorney's Office. From 1995 to 1997, they worked as a Police Officer at the Montgomery County (MD) Police Department. Gregory then joined the Drug Enforcement Administration (DEA) where they held various roles including Chief of Operations -Assistant Administrator, Chief of Staff, Managing Director, and Assistant Special Agent in Charge. At the DEA, they provided strategic leadership, guidance, and support to advance the mission and reputation of the agency. Gregory also managed international investigations and enforcement operations, supervised training programs, and developed innovative strategies to combat illicit drugs, narco-terrorism, and money laundering. After their tenure at the DEA, Gregory joined MUFG as a Managing Director - Americas - Center of Excellence, where they developed and led a global shared-services strategy for the Global Financial Crimes Division. Gregory then joined Deloitte as Vice President, where they mitigated threats and drove down risk by working on criminal investigations and providing regulatory and legal support for government and public-sector clients. Overall, Gregory has a strong background in law enforcement, strategic leadership, and financial crimes.

Gregory Cherundolo has a Bachelor of Arts degree in Political Science with a minor in Philosophy from McDaniel College. Gregory also attended the University of Virginia for Senior Supervisory Leadership Training at the School of Continuing and Professional Studies. In addition, they completed an Executive/Strategic Leadership Development Program at the Treasury Executive Institute. Gregory further enhanced their education with an Executive Leadership Development program at the University of Notre Dame's Mendoza College of Business, specifically at the Stayer Center for Executive Education. Gregory Cherundolo has additional certifications, including being a member of ASIS International and completing the Police Entry Level Training Program from the Maryland Police and Correctional Training Commission. Gregory also holds a Pennsylvania Act 120 Certification from the Pennsylvania Municipal Police Officer Education and Training Commission.