He attended the last Armor Basic Officer Leadership Course (BOLC) and Army Reconnaissance Courses (ARC) at Fort Knox, Kentucky, before it transitioned to Fort Benning (known as Fort Moore since 2023). After completing BOLC, he deployed as a scout platoon leader in 2012 to Kandahar, Afghanistan, in support of Operation Enduring Freedom.
Benjamin completed the Military Intelligence Captains Career Course in 2015 and was assigned to the 1st Armor Brigade Combat Team of the 3rd Infantry Division at Fort Stewart, Georgia. While at Stewart, he deployed in support of Operation Atlantic Resolve as the senior intelligence officer for a battalion taskforce. Following the rotation to Europe, he served as the assistant brigade intelligence officer before reassignment to the Army Evaluation Center at Aberdeen Proving Ground, Maryland. As a Survivability Evaluator, he oversaw the test and evaluation of cyber, electronic warfare, and intelligence systems; including programs such as Offensive Cyber Operations, Distributed Common Ground System-Army, Integrated Visual Augmentation System and the Cross Functional Team Synthetic Training Environment. He served as the Company Commander for the U.S. Army Test and Evaluation Command, Headquarters and Headquarters Company from April 2019 to April 2021. He was then nominated to attend the Australian Defence College for his Intermediate Level of Education (ILE) after command.
Benjamin graduated from DePauw University in Greencastle, Indiana, with a Bachelor of Arts in Anthropology and Spanish. He completed a Master of Science in Space Systems Operations with a focus in Technical Engineering from Webster University and is continuing to work towards a sequential degree in Cybersecurity. While at ILE, he completed a Master of Arts in Military and Defence Studies from Australian National University
His awards and decorations include the Bronze Star Medal, Meritorious Unit Award, Meritorious Service Medal, Army Commendation Medal, Afghanistan Campaign Medal, and a Distinguished Military Graduate of ROTC, Armor BOLC and ARC.
Benjamin is married, and the couple are avid equestrians, hikers and skiers at every duty station.