Gregory's first assignment was in Yokosuka, Japan as the assistant Resident Officer In Charge of Construction (ROICC). From there she moved to Naples, Italy to serve as the engineering and planning officer.
In 1991 Gregory moved to San Francisco, California, first as the resident officer in charge of construction, and then as the shore facility environmental compliance officer. She left the Bay Area for the Aleutian Islands to serve as the Naval Air Station Adak public works officer.
In 1995 Gregory returned to the Seabees, serving as the executive officer of Naval Mobile Construction Battalion 1 (NMCB-1), homeported in Gulfport, Mississippi, and deploying to the Western Pacific and the Mediterranean. After a tour in Washington D.C. as the chief of naval operations overseas bases planning & action officer, she went back to the Naval Construction Force, assuming command of NMCB-133, deploying throughout the Western Pacific and Mediterranean.
In 1999 Gregory reported to Naples, Italy as the officer in charge of construction, responsible for construction of a new support base and hospital. Her follow on tour was to Hawaii as the executive officer of Navy Public Works Center and NAVFAC Hawaii. Gregory then served as a Department of Defense corporate fellow, working with the Southern Company in Atlanta, Georgia.
In May 2006, she assumed command of the 30th Naval Construction Regiment in Port Hueneme, California. She reported for duty as chief of staff at the First Naval Construction Division in Norfolk, Virginia, in July 2008. Gregory was promoted to the rank of rear admiral on June 1, 2010 and assumed command of NAVFAC Pacific, in Pearl Harbor, Hawaii on July 9, 2010. NAVFAC Pacific is a command of approximately 4,000 military and civilian men and women who work for NAVFAC Pacific and its three Facilities Engineering Commands in Hawaii, Guam, and Japan.[5]
Gregory was named Iowa State University's first senior vice president for university services in July 2016 and served until her resignation in November 2017.[6][7]