2026 OCAAHS Eclipse Awardee, Cliff Gregory

Cliff Gregory, a native of Fluvanna County, is a dedicated advocate whose professional work and volunteer service reflect his commitment to opportunity, dignity, and second chances.

Cliff brings more than 25 years of professional experience in sales and financial services and holds a Bachelor of Science in Business Administration from Virginia Union University. Since joining OAR, Jefferson Area Community Corrections, in November 2023, Cliff has served as Rural Reentry Coordinator. Professionally, he assists individuals returning from incarceration with employment, housing, education, healthcare, transportation, and resources necessary for successful reentry. His efforts have contributed to more than 125 job placements throughout Central Virginia, helping individuals achieve stability, independence, and a fresh start.

Beyond his professional responsibilities, Cliff has made volunteer service to the Orange County community, particularly underserved residents and people of color, a personal priority. He dedicates numerous hours each week to Good Samaritan, Inc. in Orange, supporting individuals and families in need. Cliff’s service is handson: he unloads deliveries, stocks shelves, organizes resources, prepares food, and coordinates volunteers to ensure neighbors receive needed assistance.

Cliff has also volunteered as an adult education tutor, helping individuals work

toward earning their GEDs and creating pathways to greater opportunity. Married and the proud father of three adult children, Cliff lives by the motto, “If your idea of success only benefits you, you’re really not successful.” His life of service demonstrates that success is most meaningful when it creates opportunities for others to rise.