Major Drew Hess is a native of Rockford, Illinois, and graduated from Guilford High School in 1991.  Upon graduation, Drew attended the University of Iowa for one semester before transferring to the University of Illinois.  He graduated in 1996 with a Bachelor of Science degree in Finance and earned his aviation mechanics license.  While in high school and college, Drew participated in swimming and competitive water-skiing where he and his water-ski team won numerous state championships and a national championship in 1991.

Drew was commissioned through the Platoon Leaders Class (PLC) program in 1996 and reported to The Basic School in Quantico, Virginia. Upon completion, he reported to Naval Air Station (NAS) Pensacola, Florida, to begin primary flight training. In December 1998, Drew reported to Training Squadron 31 (VT-31) at NAS Corpus Christi, Texas, to fly the TC-12 Huron and received his wings of gold in July 1999.

In August 1999, Drew reported to Marine Aerial Refueling Transport Training Squadron 253 (VMGRT-253) at Marine Corps Air Station (MCAS) Cherry Point, North Carolina, to begin training in the KC-130. He then reported to his first fleet squadron Marine Aerial Refueling Transport Squadron (VMGR-352), the "Raiders," at MCAS Miramar, California, in June 2000. While with the "Raiders," Drew served as the logistics officer and as the powerline division officer. During this tour, Drew deployed to Pakistan in support of Operation Enduring Freedom as well as to Bahrain in support of Operation Iraqi Freedom.

Following his first fleet tour, Drew reported to VMGR-152, the "Sumos" at MCAS Futenma, Okinawa, Japan, in February 2004. While assigned to the "Sumos," Drew served as the aviation safety officer, aircrew training officer and Naval Air Training and Operation Procedures Standardization (NATOPS) evaluator. Drew's next assignment came in December 2005 as the Third Marine Expeditionary Force (III MEF) Tactical Exercise Control Group (TECG) air officer. During his time in the fleet, Drew has flown more than 250 combat hours. He also has flown numerous missions in support of operations and exercises in Sri Lanka, Mongolia, Thailand, the Philippines, the Republic of the Marshall Islands, South Korea, Guam, Wake Island, American Samoa, Iwo Jima, Australia, Canada, Spain, Portugal, Scotland, Italy, Greece, Afghanistan, Kuwait, and Iraq.