Lt. Col. Drilling enlisted in the Kentucky National Guard in 2004 and reported to basic training at Fort Leonard Wood, MO as a Private First Class (Military Police); contracted into the Simultaneous Membership Program as an ROTC cadet at Eastern Kentucky University until commissioning as an active-duty Quartermaster officer (2006). Since commissioning, she has held various leadership positions as an Active Duty, Active Guard/Reserve (AGR) and Troop Program Unit (TPU) officer including Deputy Commanding Officer and Executive Officer (7th Psychological Operations Group, Mountain View, CA (AGR)); Executive Officer and Readiness Operations Officer, (United States Army Reserve Command G-33, Fort Liberty, NC (AGR)); Company Commander and Small Group Instructor (United States Army John F. Kennedy Special Warfare Center and School (SWCS), Fort Liberty, NC (AGR)); Collective Training and Unit Training OIC (United States Army Civil Affairs and Psychological Operations Command (Airborne) G-37, Fort Liberty, NC (AGR)), Company Commander and S-4 OIC (Headquarters and Headquarters Company, 15th Psychological Operations Battalion), Cincinnati, OH (TPU)); Executive Officer and Detachment Commander (340th Psychological Operation Company, Garner, NC (TPU)); Executive Officer and Platoon Leader (196th Quartermaster Detachment), Fort Campbell, KY (AC)), Platoon Leader (20th Quartermaster Company), Fort Campbell, KY (AC). Lt. Col. Drilling participated in two deployments in support of Operation Iraqi Freedom: 2008-2009 and Operation Enduring Freedom: 2011-2012.
Lt. Col. Drilling attained her Master of Science Degree in Safety, Security, and Emergency Management (2010) and a Bachelor of Science Degree in Criminal Justice (2006), from Eastern Kentucky University. She additionally earned a Master of Arts Degree for Defense and Strategic Studies from the U.S. Naval War College (2017) upon completing the College of Naval Command and Staff, Newport, RI. She additionally graduated from Quartermaster Captain Career Course (SWCS), Fort Liberty, NC, and the Quartermaster Officer Basic Course, Fort Gregg-Adams, VA. While serving as a USAR TPU, she had the privilege of serving the citizens of Kentucky for over three years as a Trooper for the Kentucky State Police, Post 8, Morehead.
Lt. Col. Drilling's awards and decorations include the Bronze Star Medal, Meritorious Service Medal w/OLC (3d Award), Combat Action Badge, Senior Parachutist Badge, Parachute Rigger Badge, Basic Instructor Badge, German Proficiency Badge – Gold, German Armed Forces Parachutist Badge, and Royal Netherlands Armed Forces Parachute Badge.
Lt. Col. Drilling has been married for four years, her and her husband have one child, and two rescued cats.