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Diedre Windsor

Diedre L. Windsor is the founder of Windsor Group LLC, a professional services company based in Chevy Chase, Maryland. A native of Detroit, Michigan, enlisted in the US Army in October 1986. Upon completion of initial training she served in Germany and later at Fort Bragg, North Carolina as a paratrooper with the elite 82nd Airborne Division. In 1992 Diedre was awarded an Army Green to Gold Scholarship resulting in her transition from the enlisted to officer ranks. Diedre was commissioned a Regular Army Air Defense Artillery (PATRIOT Missile) Officer and later transitioned to the Adjutant General Corps (Personnel). She retired from active service in September 2009 as a Major.

Upon retiring from the Military, Diedre continued along her public service path by joining the federal government. She assumed roles at the U.S. Department of Education first as Chief of Staff to the Federal Student Aid Chief Information Officer and Technology Office and later as Executive Officer and Director of Resources for the Officer for Civil Rights. After five years at Education, Diedre joined the career Senior Executive Service (SES) with the Department of Justice (DOJ), U.S. Trustee Program (USTP) as the Deputy Director for Management.

Diedre left the federal government in late 2016 to pursue entrepreneurship full time. Her company, Windsor Group, LLC, provides a host of professional services and business solutions to public and private sectors. The company’s core services include, Staffing, Training, IT Support and Program and Project Management.

Diedre graduated from Methodist University in 1994 with a Bachelor of Science in Political Science and from Webster University in 2011 with a Master’s Degree in Human Resource Management. Ms. Windsor resides in Chevy Chase, Maryland with her family. 

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