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Weston Henry has held a number of roles in the tech industry since 1999. Weston began their career as the Owner of Ignus Technologies in 1999. In 2010, they became President of Insight Technologies, Inc. and Partner at ConnectBooster, where they were responsible for the Payments Acceptance Automation tool integrated into the ConnectWise PSA platform and QuickBooks accounting. In 2012, they became Owner/CIO, President of Software Development, and CEO of TrueIT LLC.

Weston Henry attended East Grand Forks Senior High from 1980 to 1985. Weston then went on to attend the University of North Dakota.