Pittard received his commission as an Armor officer in 1981. His first operational assignment was with the 1st Infantry Division (Mechanized) at Fort Riley, Kansas in 1982. He served as a Tank Platoon Leader and Tank Company Executive Officer in 2-63 Armor; then as a Scout Platoon Leader and Battalion S1 in 3-37 Armor. In 1984, he served as an Admissions Officer at the United States Military Academy; and in 1985 was assigned to Bad Kissingen, Germany, as the Squadron S4 for 2nd Squadron, 11th Armored Cavalry Regiment (ACR).