Jon DeLena

Senior Managing Director

Jon DeLena brings over 30 years of experience in law enforcement, investigations, and security to his role as Senior Managing Director at Guidepost. Specializing in complex investigations, Mr. DeLena has a distinguished history of leadership and accomplishments. His career includes conducting intricate domestic and international investigations and holding pivotal leadership positions, culminating in his role as Associate Administrator of the DEA, the agency’s #3 position worldwide.

As the DEA’s Chief Operating Officer, Mr. DeLena oversaw all business operations, where he provided transformative leadership grounded in practical execution for the DEA, an organization with 10,000 employees and 330 offices in 70 countries. Mr. DeLena steered all business, financial, and administrative functions while he took the lead in building a more efficient, resilient, and future ready operation to advance the agency’s mission and increase its impact, both in the United States and around the world. He leveraged his decades of experience in investigative leadership to implement business-minded solutions that allowed the DEA to better address threats, mitigate risk, and ensure compliance.

Mr. DeLena transformed the DEA’s congressional and media divisions to expand awareness of the DEA’s mission and goals, expanding visibility and inspiring action among government officials and members of the public, while overseeing matters related to the media, public affairs, government relations, and community outreach.

Mr. DeLena’s investigative successes have leveraged both traditional law enforcement methods and cutting-edge technologies. His career has been marked by a steadfast dedication to community protection and the DEA’s mission, driven by a relentless work ethic and a commitment to justice and public service.

During the height of the fentanyl crisis, Mr. DeLena was instrumental in creating the DEA Family Summits on Fentanyl and the Faces of Fentanyl memorial at DEA Headquarters. These initiatives provide critical support and resources to affected families and have inspired other federal agencies to replicate DEA’s efforts.

Key career highlights:

  • Chief Operating Officer, DEA: Oversaw global business operations, which included Compliance, Financial Management, HR, IT, and others.
  • Testified before the United States Congress on multiple occasions to increase awareness of the DEA’s relentless pursuit of the cartels responsible for the current fentanyl epidemic.
  • New England Division, DEA: Infused energy, expertise, and commitment into directing international investigations during the fentanyl crisis.
  • Sensitive Investigations Units (SIU) Program: Managed sensitive and complex foreign law enforcement teams, highlighting DEA’s collaboration with vetted foreign law enforcement and intelligence professionals. Enabled and enforced compliance.
  • New England and Northern U.S. Border: Collaborated with federal, state, and local law enforcement to streamline investigations, increasing seizures and arrests.
  • Section Chief- Office of Special Projects. Oversaw the implementation of the DEA Drug Flow Attack Strategy (DFAS) which aimed to disrupt the flow of drugs, money, and chemicals between source zones and the United States through intelligence-driven enforcement, sequential operations, and predictive intelligence. He coordinated closely with DEA’s Foreign Deployed Advisory Support Team (FAST) and U.S. Military Special Operations forces to counter drug trafficking.

Mr. DeLena’s tenure at the DEA included various key roles, each enhancing his investigative and leadership skills:

  • DEA Chief of Congressional and Public Affairs (HQ, Arlington, VA)
  • DEA Deputy Special Agent in Charge, Senior Executive Service (New England Division, Boston, MA)
  • DEA Assistant Special Agent in Charge (Northern New England Office, Manchester, NH)
  • DEA Group Supervisor (Miami Division, FL)
  • DEA Special Agent (Colorado and Florida Divisions)

Recognized for his leadership, Mr. DeLena has received numerous awards and commendations, including the Presidential Rank Award granted by the President of the United States for “sustained extraordinary achievement.” He is committed to outreach, prevention, and education, particularly youth empowerment, and has been featured in national and regional media interviews and was often called upon for presentations on fentanyl and community engagement.

Did you know?

In September 2023, I proudly served as the master of ceremonies at the DEA’s 50th anniversary celebration, attended by past and present DEA employees, former administrators, senior Justice officials, and U.S. Congress members. This was particularly personal to me after serving the agency for 28 years.


  • Master of Science in Executive Leadership, Champlain College, Graduation Honors
  • Bachelor of Arts in Sociology, University of South Florida