Officer Singletary started his career in law enforcement in 2001. He began riding a police motor his first year as a Law Enforcement Officer. He was hired with the Holly Springs Police Department in 2006. Officer Singletary completed motor school through the Holly Springs Police Department in 2011, and became a part of the Holly Springs motor unit. In addition to the motor unit, Officer Singletary is a domestic violence Officer, a member of the Crisis Intervention Team, and is on the Police Bicycle Team.