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Jonathan Boswell has a diverse work experience that spans various industries. Jonathan began their career at Thought Convergence as a General Manager from September 2008 to September 2009. Jonathan then ventured into investments and served as the President of Boswell Investments, Inc. from September 2009 to September 2011. Jonathan then took on the role of COO at Senico Labs, LLC from September 2011 to an unknown date in 2014. During their time at Senico Labs, LLC, they oversaw significant growth and managed multiple internet businesses. Jonathan then moved on to ArborBridge where they served as the CTO from December 2014 to January 2020. Jonathan continued to expand their expertise in the technology field and joined General Assembly as a Distinguished Faculty Member from September 2016 to an unknown date. Currently, they work at PlayVS, where they started as an Engineering Manager in January 2020 and then progressed to become the Director Of Engineering in January 2022.

Jonathan Boswell earned a Bachelor of Fine Arts (BFA) degree in Motion Picture, Television & Recording Arts from Florida State University, which they attended from 1998 to 2001. Prior to that, they attended Westminster Academy. No specific start or end year was provided for their time at Westminster Academy, and no degree or field of study was included.