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Alan Greenwood has a diverse work experience spanning over three decades. Alan began their career as a Marine in the U.S. Marine Corps in 1988 and served till 1997. After that, they joined the Marine Corps Systems Command as a Riverine Craft Project Officer from July 1999 to July 2002. In 2003, they joined U.S. Forces Korea as a Korean Exercise Planner until July 2005. From August 2005 to December 2008, Alan worked as a Program Analyst at the Pentagon for the U.S. Marine Corps. In 2007, they briefly served as a Planner at Multi-National Corps Iraq from December 2007 to June 2008. Alan then transitioned to Systems Planning and Analysis, Inc in 2009, where they took on various roles, including Systems Engineer from January 2009 to October 2011, Program Manager from October 2011 to September 2015, and currently as a Program Analyst since September 2015.

Alan Greenwood attended the United States Naval Academy from 1984 to 1988, earning a Bachelor of Science degree in Political Science. In addition, they obtained a certification in Project Management Professional from the Project Management Institute in September 2015.