Major Heywood enlisted in the Marine Corps in July 1999, and upon graduation from MCRD, Parris Island, Major Heywood reported to the Defense Language Institute (DLI) in Presidio of Monterey, CA where he conducted Arabic language studies. Following his graduation from DLI in 2001, he reported to the Marine Detachment in Goodfellow Air Force base for follow on Cryptologic training.
Upon completion of the Cryptologic training, Major Heywood reported to Radio Reconnaissance Platoon, 2nd Radio Bn where he began the Radio Reconnaissance Indoctrination Program (RRIP). After completion of the RRIP, Major Heywood, continued with the reconnaissance pipeline training, graduating from the Amphibious Reconnaissance School (ARS), Army Airborne School, and Survival Evasion Resistance Escape (SERE) school.
In 2003, Major Heywood served as lead Arabic Cryptologic Linguist and Pointman on a Radio Reconnaissance Team deployed to Iraq ISO of OIF. In 2004, Major Heywood served as Team Leader for the Radio Reconnaissance Team onboard the 22nd MEU deployed to Afghanistan ISO OEF. After voluntarily extending his enlistment twice on the deployment, and returning back to the United States November 2004, Major Heywood ended his active service to pursue college studies.May 2008, Major Heywood received a Bachelors of Science in Computer Science from the University of North Carolina at Wilmington, graduating at the top his class with summa cum laude honors. Major Heywood continued to the private sector to develop software for commercial and military aviation platforms. In 2009 Major Heywood began making preparations to return to the Marine Corps Reserves as a commissioned officer.
March 2010, Major Heywood graduated Officer Candidate School and received a direct reserve commission as a Second Lieutenant in the Marine Corps Reserves. After graduating The Basic School (TBS) November 2010, and earning the Iron Mike Award, Major Heywood reported to the Marine Combat Engineer School in Camp Lejeune, NC to attend the Combat Engineer Officer course.
April 2011, Major Heywood graduated from the Combat Engineer Officer course, and reported to C Co. 4th Combat Engineer Battalion (CEB), 4th MARDIV where he served as Platoon Commander and XO from 2011 - 2013 in the Selected Marine Corps Reserve (SMCR). In his civilian capacity, Major Heywood performed cyberspace capability development for a variety of organizations within the Intelligence Community (IC), and began his graduate studies in Computer Science.
Towards the end of his tour with C Co. 4th CEB, Major Heywood was selected to mobilize ISO Marine Corps Forces Cyberspace Command (MFCY). From 2014 - 2016, Major Heywood was mobilized on Active Duty orders and served as a Cyber Research and Development Officer and Combat Support Team Leader leading development of cyber capabilities for the emerging Marine Cyber Mission Force. While assigned to MFCY, he completed a Master of Science in Computer Science with cum laude honors from Drexel University, PA, and attended the Marine Intelligence Officer Course, concluding an MOS lateral move and becoming an Intelligence Officer.
Upon completion of his mobilization, October 2016, Major Heywood reported to the Office of Marine Forces Reserve G-9 assuming the role as Cyberspace Planner where he supported the build out of the defensive cyberspace capability in the SMCR . In October 2018, Major Heywood was selected to assume his current role as Company Commander, B Co, Defensive Cyberspace Operations, Force Headquarters Group, Marine Forces Reserve.