Herb began his career in government service as a second lieutenant in the 24th Infantry Division, Fort Stewart, Georgia. Over the next 10 years, he was stationed at Fort Sam Houston, Texas; Fort Meade, Maryland; Bangkok, Thailand; and Fort Lee, Virginia. Herb left active duty to start a career in finance and investments, serving customers at Edward Jones, Signet Financial Services, Bank of America, and Colonial Downs. 

Herb was elected as  county treasurer for New Kent in 1999 and served three terms. During that time, he remained in the US Army Reserves. He was called up twice after 9/11 and served here in Virginia, then two tours in Iraq. In 2011, Herb decided not to run for a fourth term as county treasurer.  He accepted a position with the federal government as an operations officer in Afghanistan in 2012. He served in that capacity until November 2014. Herb retired in 2012 as full colonel. 

As a result of his extensive military knowledge and experience, Herb was appointed by Virginia Governor Ralph Northam to his Military Advisory Council. In 2014, Herb and his brother, Michael, started Pyramid Technologies, LLC, a cloud-computing, project management, and logistics firm. He currently serves as the co-founder and CEO of Pyramid. Herb is a long time member of Omega Psi Phi Fraternity, Incorporated. He and his wife, Yvonne, reside in the Providence Forge area of New Kent County. Yvonne is a retired educator who served as the principal at New Kent High School for 14 years. They have two sons and one grandson.

"There is a desperate need for criminal justice reform to keep all of our communities safe. This includes federally legalizing marijuana and ending the war on drugs that has disproportionately incarcerated people of color for decades." campaign website