Sergeant Major Dobson graduated from Clinton Prairie High School and entered the delayed enlistment program between his junior and senior year. Upon graduation, He shipped to Marine Corps Recruit Depot San Diego, CA. in 1990.

Upon completion of his initial training he was designated a Field Radio Operator. During 1991, Lance Corporal Dobson was assigned to Bravo Battery 1st Bn. 10th Marines for duty where he served as a Radio Operator for the liaison section and subsequently served as the Radio Chief. In March 1992 he was promoted to Cpl (Meritoriously) and was then assigned as the liaison section chief while in direct support of 2d Bn 2d Marines. During this period Cpl Dobson completed one LF6F deployment participating in Operations Provide Promise in the Adriatic Sea and Support Democracy in Haiti. He was promoted to the rank of Sergeant in January 1994. During the end of 1994 Sergeant Dobson was then transferred to the School of Infantry for a short time where he served as a communications instructor to the SNCO Academy as well as the Range Scheduler for the School of Infantry.

During the middle of 1995 Sergeant requested and received orders returning him to the Operating Forces where he was reassigned to 1st Bn 10th Marines. During this period Sergeant Dobson completed another LF6F deployment participating in Operations Quick Response and Assured Response as the Battery Radio Chief. Upon returning from deployment in 1996 Sergeant Dobson requested and received orders to the Drill Field. Upon completion of Drill Instructor school in 1997, Sergeant Dobson was assigned to Kilo Company 3rd Recruit Training Battalion where he served as a Drill Instructor and Senior Drill Instructor.

He was promoted to Staff Sergeant in March 1998. In 2000, upon completing a successful tour on the Drill Field, Staff Sergeant Dobson received orders to 2d FSSG. He was assigned as the Electronic Key Management System (EKMS) Manager for the 2d FSSG responsible to the Commanding General for all Cryptographic hardware and software in the 2d FSSG. He was promoted to Gunnery Sergeant in April 2001.

In August 2001 Gunnery Sergeant Dobson was reassigned to Communication Company where he served as the Company Gunnery Sergeant and Company First Sergeant until August 2003. From January 2001 to March 2002 Gunnery Sergeant Dobson deployed as a member of JTF-160 in support of Operation Enduring Freedom conducting Detainee Operations in Guantanamo Bay, Cuba.

In February 2002, Gunnery Sergeant Dobson deployed to Kuwait in support of Operation Enduring Freedom and Iraqi Freedom.

Upon returning from deployment in May 2003, Gunnery Sergeant Dobson was assigned as the Company First Sergeant of Communication Company where he stayed until August 2003. In August 2003, Gunnery Sergeant Dobson was assigned to the position as the Company First Sergeant of Service Company H&S Bn. 2d FSSG.