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Drew Bolling has worked as a Document Management Specialist at CNA Inc. from June 2014 to August 2014. They later joined Systems Alliance, Inc. in August 2015 as a Technical Support Engineer and then transitioned to the role of DevOps Engineer in July 2017, where they focused on automating key business operations and maintaining system functionality for client satisfaction. The end date for their role as DevOps Engineer is not specified.

Drew Bolling earned an Associate's degree in Computer and Information Sciences, General from Carroll Community College between 2011 and 2013. From 2013 to 2015, Drew pursued a Bachelor's degree in Information Technology: Network Design at Stevenson University.