She enlisted in the Massachusetts Army National Guard as a helicopter mechanic and served as a traditional (National Guard) soldier before receiving a commission as a Second Lieutenant as a Signal Officer. 

She served in Active Guard and Reserve (AGR) positions for more than 18 years at the state and national level.  Various assignments include Personnel staff officer; Program Manager for Line of Duty claims; Program Evaluation Group (PEG) analyst, Executive Officer for the Army National Guard Chief Resource Management Officer (G-8).  Colonel Leonard was selected to become a Legislative Liaison for the National Guard Bureau where she managed Joint Programs to include National Guard Military Construction.  She was assigned to the Army Budget Legislative Liaison office where she oversaw Army Active Duty and Reserve Component Military Construction programs, Family Housing and Environmental Programs.  She returned to the National Guard Bureau Legislative Liaison office to work Army National Guard specific programs for the Director of the Army National Guard.

Colonel Leonard holds a Bachelors of Science in Human Services from Fitchburg State College and a Masters of Public Administration from Troy State University.