Over the course Mr. Leo's career since 1980, he worked in Security and Privacy as a contractor for NASA at the Johnson Space Center from 1980 to 2002, in his final years in the role of Program Manager, Chief Security Architect and Chief Security Officer for Mission Operations for the Shuttle and Space Station programs. In 2002, he worked for the University of Texas-Galveston and Chief Information Security Officer and Director of IT for the Correctional Managed Care Division, establishing a complete security, privacy and compliance program for the organization. Upon departing there in 2006, he began a new career chapter as a security and privacy consultant entirely devoted to Healthcare compliance for his clients

He is a Charter member of the EC-Council Certified Hacking Forensic Investigator (CHFI) Advisory Board, a global panel of experts working to establish professional standards and practices in data forensics and serves on scientific working groups at NIST in both Cloud Security and Forensics. He serves on The American Board of Forensic Engineering and Technology (ABFET) for The American College of Forensic Examiners Institute (ACFEI) and holds several certifications from ISC2 and ISACA. Mr. Leo has been accorded Fellow status for the American Board for Certification in Homeland Security (ABCHS).

Mr. Leo has provided Expert Witness services in several cases concerning compliance issues with regard to the impact of HIPAA on the subject matter and privacy violations.