Keith Allen was an infantryman with the United States Army before starting a 19-year career with the United States Postal Service (USPS). In 1996, while employed as a tractor-trailer operator with USPS, Allen enrolled at Bristol Community College to pursue an electrical engineering degree. He earned a Bachelor of Science in Electrical Engineering from the University of Massachusetts, Dartmouth, in 2004 and became a member of Phi Theta Kappa and Eta Kappa Nu Honor Societies during this time.

In 2006, Allen transferred to the Department of Veterans Affairs in Tampa, Florida. While in Tampa, he held the positions of general engineer, chief of projects, and chief of maintenance and operations. In 2013, he accepted the position of director of facilities management with VA Puget Sound Health Care System in Seattle, Washington. He graduated from the National Defense University, in July 2016, with a Master of Science in National Strategic Resourcing. Allen was most recently the deputy director for VA Puget Sound Health Care System before becoming the permanent medical center director at the Roseburg VA Health Care System.