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Olivia Diehl has a long history of work experience. Olivia began their career in 2006 as a Contracts Summer Intern with Northrop Grumman Corporation. In 2007, they were an Engineering Design Summer Intern with the same company. In 2008, they were a Subcontractor Management Summer Intern, and in 2009 they were a Finance Summer Intern. In 2010, they were a Contracts Administrator with Huntington Ingalls Industries (formerly Northrop Grumman Corporation). From 2011 to 2014, they were a Contracts Representative with Leidos (formerly SAIC). From 2014 to 2018, they were a Contracts Manager and a Contracts Administrator III with CACI International Inc. Finally, since 2018, they have been the Director of Contracts with Northstrat Incorporated.

Olivia Diehl obtained a BA in Economics from the University of Virginia. Olivia then went on to receive a Master of Business Administration - MBA from William & Mary's Raymond A. Mason School of Business in 2020. Additionally, they hold a Graduate Certificate in Procurement and Contracts Management from the University of Virginia.