After graduating from UCLA and attending law school, Randy served as Counsel (Section Chief) for the FDIC/RTC where he provided general counsel to failed financial institutions with assets in excess of 15 billion dollars. After 7 years, he moved from the executive branch to the judicial branch of the federal government. In 2017, Randy retired as the Chief Deputy the of California Central District Court. As the chief operations officer of the largest federal trial court in the country, he provided judicial case and trial support services to the nearly 60 judges and 500 Clerks Office and chambers employees and oversaw 14 departments.

Randy and his wife, Lissen Gregory, live in Manhattan Beach, California. They have two adult sons that live nearby. Randy has served as the president of the UCLA Alumni Association Board of Directors and as a member of the UCLA Foundation Board of Directors. He has served as a Small Group Leader at PIVOT. He also is a member of the McIntyre House Board of Directors.