[7] She participated in the Junior Reserve Officers' Training Corps while attending Santa Barbara High School, from which she graduated in 1986.

[3] Following company command, Holland earned a Master of Arts degree at Duke University en route to a teaching assignment at the United States Military Academy,[3] where she served as a faculty member in the history department from 1999 until 2002.

Returning from Iraq, she then served as a plans officer in the Operations Directorate, United States Central Command at MacDill Air Force Base in Tampa, Florida.

[10] On 15 December 2015, Holland was announced as the 76th Commandant of the Corps of Cadets at the United States Military Academy, the first woman to serve in that position.

[3][11][13] In July 2017, Holland assumed command of the South Atlantic Division, United States Army Corps of Engineers, headquartered in Atlanta, Georgia.

[15] In the first six months in this assignment, she oversaw the Corps of Engineers' support to Florida, the United States Virgin Islands, and Puerto Rico following Hurricanes Irma and Maria.

[16] In October 2020, Major General Holland was appointed the 41st President of the Mississippi River Commission, the first woman to hold that position.