Reginald Hammond earned a Bachelor of Business Administration degree from the University of Pennsylvania in 1996 and went on to receive a Master of Business Administration Degree from Drexel University in 2000. 

Reginald Hammond began his career with the Philadelphia Prison System as a correctional officer in 1981.  Mr. Hammond has been assigned to Holmesburg Prison, the Detention Center (promoted to the rank of sergeant), the House of Correction (promoted to the rank of lieutenant), and the Curran-Fromhold Correctional Facility (promoted to the rank of captain).  As a captain, he was responsible for the central intake for all adult males for the PPS at the Curran-Fromhold Correctional Facility and was instrumental in helping the PPS undertake and adapt to the challenges of a population explosion while the PPS was operating under a court-imposed admissions moratorium.

Under his leadership, the Curran-Fromhold Correctional Facility Admissions and Diagnostics Unit was honored as Unit of the Year in 1998.  Following his stint at Curran-Fromhold Correctional Facility, he was promoted to the rank of Deputy Warden and assigned to the Detention Center. Then Deputy Warden Hammond was assigned as the Director of the Policy and Audit Division in October of 1999.  In this capacity, he found new and innovative ways to systematize the policy development and revision processes in addition to streamlining policy implementation and bringing the division up to speed with ever-changing advancements in computer technology. 

Deputy Warden Hammond was promoted to Warden in August 2001 and assigned to the House of Correction. He was assigned to the Detention Center in April 2002; then assigned to the Curran-Fromhold Correctional Center in May 2003.  He was chosen to be temporarily promoted to the rank of Deputy Commissioner for Policy, Training and Special Services in December 2003. This promotion became permanent in July 2004. Deputy Commissioner Hammond took on new responsibilities in October 2005 as the Deputy Commissioner for Restorative and Transitional Services. This new title reflects the system's increasing focus on reentry programming and services.