John G. Connolly

Senior Managing Director
John Connolly in a suit and tie smiling for a professional photograph

John G. Connolly brings a distinguished three-decade tenure with the U.S. government to his role as Senior Managing Director at Guidepost. He provides invaluable guidance to clients worldwide, navigating the complexities of U.S. customs, immigration, and visa processes. Mr. Connolly has played a pivotal part in high-profile projects, including serving on the monitoring team for a leading global financial institution and participating in a trade compliance audit for a prominent international corporation

Mr. Connolly’s expertise extends to advising multinational corporations on adherence to federal immigration laws, focusing on nonimmigrant visa regulatory compliance and reviews and remediations of Employment Eligibility Verification forms and the E-Verify processes, including identity fraud assessments and fraud detection training. He has also worked with firms in conducting due diligence investigations as well as providing subject matter expertise in support of litigation.

Mr. Connolly’s government service included various executive positions, notably as the Deputy Executive Associate Director for the Department of Homeland Security, Homeland Security Investigations (HSI). In this capacity, Mr. Connolly directed a broad spectrum of management operations, overseeing complex investigations into money laundering, intellectual property rights infringements, and customs and immigration violations.

His leadership extended to the development and implementation of policies and procedures, steering the strategic course for over 9,000 personnel across 185 domestic facilities and 67 international offices spanning 48 countries. Mr. Connolly is credited for promoting and reinforcing strong and transparent communications, both internally and externally with other law enforcement entities, other federal agencies and organizations, and senior government leaders.

Did You Know?

John had many jobs during high school and college before beginning his career with the United States government… including working for a portable toilet company and his hometown cemetery.


  • Bachelor of Science, Criminal Justice, Northeastern University
  • Senior Executive Fellows Program, Harvard University Kennedy School of Government