Matthew J. O’Brien

Managing Director

Matthew J. O’Brien brings over two decades of leadership in global investigations, security strategy, and risk management to Guidepost Solutions. He has directed high-stakes investigations and security operations across domestic and international jurisdictions including Mexico, Central America, Europe, and the Middle East.

As a former Assistant Special Agent in Charge with the Drug Enforcement Administration (DEA), led internal and external investigations from sensitive workplace matters to money laundering (including cryptocurrency), and the diversion of controlled substances, drug trafficking and violent crime.

Mr. O’Brien’s DEA career also included pivotal roles as Acting Chief of Foreign Operations and Section Chief of the Mexico, Central America, and Canada section of Special Operations Division, leading multi-agency investigations targeting transnational criminal networks and oversight of DEA enforcement activities in 69 countries. His work included managing joint teams from law enforcement, intelligence, and military agencies. Notable experience includes:

  • Spearheading bilateral investigations in Guatemala, Honduras, Mexico, and Panama, resulting in the arrest and extradition of high-level criminal operatives.
  • Staff Coordinator for the Special Operations Division’s Mexico, Central America, and Canada section which was responsible for executing the majority of the DEA’s international investigations.
  • Directed pivotal cross-border investigations in collaboration with US and foreign intelligence and law enforcement agencies.
  • Managed and conducted investigations in South and Central America, indicting senior operatives in Colombia, Venezuela and the Middle East.
  • Establishing first-of-their-kind alliances with law enforcement and judicial authorities in Belgium, Colombia, Denmark, Ghana, Italy, the Netherlands, Panama, Romania, and Spain.
  • Leading sensitive workplace investigations and threat assessments and implementing robust security programs to minimize operational risk.

Mr. O’Brien began his DEA career in New York City, where he led major cases that resulted in the conviction of top-ranking international crime figures. He also brings corporate experience in business development and fraud investigations from his time at Cintas Corporation.

Mr. O’Brien has received the DEA Administrator’s Award and multiple commendations from the U.S. Attorney’s Office, Southern District of New York.

Education

  • Bachelor of Science, Business Administration, Georgetown University, McDonough School of Business
  • Executive Program in Strategic Leadership, Notre Dame University, Mendoza School of Business

Affiliations

  • Atlanta/Carolinas HIDTA (High Intensity Drug Trafficking Area), Executive
  •  Association of Federal Narcotics Agents (AFNA)
  •  Federal Law Enforcement Officers Association (FLEOA)

Certifications

  • Top Secret/SCI Security
  • Chainalysis Reactor Certification
SBC hotline
Oakland County AAR
MAGELLAN Monitorship