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Harold S. began their career in 2004 as a Software Engineer at SAIC. In 2005, they moved to NT Concepts as a .NET Developer. In 2007, they joined InfoReliance as a .NET Developer. In 2008, they became a Mobile Architect and .NET/SharePoint Developer at Twin-Soft Corporation. In 2009, Harold S. founded RxmindMe, LLC, where they were an Apple iOS Developer, Architect, and Owner. In 2011, they became President and CTO of OGi - OGinternational. In 2012, they joined Fixmo as a Senior Architect. In 2014, they founded Monkton Consulting, LLC. Finally, in 2016, Harold S. became Co-Founder and CEO of Monkton, Inc.

Harold S. attended Virginia Tech from 2000 to 2004, where they earned a Bachelor of Science degree in Computer Science.