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Lemaire Stewart has had a lengthy career in software engineering. In 2018, they founded Goodfynd. Prior to that, they worked at EPAM Systems as a Senior Software Engineer, Sitecore from 2015-2018, NavigationArts as a Sitecore Developer from 2013-2015, Booz Allen Hamilton as a Software Engineer, Senior Consultant from 2009-2013, and Chenega Federal Systems as an Intern Contractor in 2008. At Booz Allen Hamilton, they were a SQL and .NET(C#) Web Application Developer for the Federal Aviation Administration and lead .NET development. At Chenega Federal Systems, they developed a GUI using the Qt C++ library and created an XML schema to save the attributes of an embedded system model.

Lemaire Stewart obtained a Bachelor of Science in Electrical & Computer Engineering from Virginia Tech between 2004 and 2009. In 2013, they obtained a Sitecore 7 certification from Sitecore. Lemaire also obtained a ScrumMaster certification from the Scrum Alliance in 2009. In 2013, they went on to pursue a Master of Science in Computer Software Engineering from George Mason University, which they completed in 2015.