MSgt Jolly spent nearly 18 years in the United States Marine Corps; over a decade as an operator in a joint special missions unit in Ft. Bragg, NC. During that time, he went on over a dozen combat deployments to Afghanistan, Iraq, Syria, and numerous other countries in Africa and the Middle East. He served as a team leader, squad leader, and Platoon Sergeant in the United States Marine Corps infantry and as an operational team member and team leader in a joint special missions unit designated for hostage rescue and targeting high value individuals. MSgt Jolly has completed missions ranging from overt large scale ground combat in Iraq and Syria, to singleton covert operations in the Middle East and Africa. 

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Since his retirement in 2019, he has worked with SWAT teams across the US, teaching close quarters combat, shooting, covert operation techniques, tactics and procedures, and a variety of other topics. He has helped develop and improve clandestine communication equipment through a company called IT2 and works as an instructor for the new IVAS system, formerly known as the Microsoft Holo lens. He is an operating partner for The Sentinel Foundation, a non profit through which he conducts covert child rescue around the world. His time as an operator in a special missions unit afforded him the opportunity to work under extremely stressful circumstances in a variety of locations, which has given him the experience he needed to transition into civilian life and contribute outside the Department of Defense.