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Shawn Bennett's work experience begins in 2009 as a Proposal Specialist at UNICOM Government Inc. From there, they worked as an Account Manager at Deltek before joining Primescape Solutions, Inc. as a Business Development Manager. In 2013, they became a Business Development Manager at THE CENTECH GROUP, Inc.

In 2014, Bennett joined Emagine IT, Inc. as a Business Development Manager/Program Manager NIH CIO-SP3 Small Business, and later served as a Senior Business Development Manager.

In 2016, they transitioned to Definitive Logic, where they held multiple roles, including Senior Manager, Assistant Director, Director of Federal Business Development & GWACs, and Program Manager of NIH CIO-SP3 Small Business.

In 2021, Bennett worked as the Principal Owner of Digital Government Strategies. Shawn also spent time at Insight Technology Solutions as the Director of Business Development before becoming the Chief Growth Officer.

Shawn Bennett attended George Mason University from 2003 to 2009, earning a Bachelor of Science (BS) degree in Business Management. In 2007, they also briefly studied at the University of Canberra, focusing on Marketing/Marketing Management, General.