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Dylan Orlady started their work experience as a Work Study Student at the University of the South from August 2008 to May 2012. Dylan then worked as a Graphic Designer at Shamrock Matting from September to December 2012. In the same year, they also worked as a Graphic Designer at Sea Waves LLC from September 2012 to November 2013. From July 2013 to December 2018, they served as the Director of Analytic Services at Enterprise Risk Strategies, LLC. Currently, they hold the position of Chief Operations Officer at Khona Scientific, Inc since December 2020.

Dylan Orlady completed their high school education at Highlands Ranch High School from 2004 to 2008. Following this, they pursued their Bachelor of Fine Arts (BFA) degree at The University of the South from 2008 to 2012, majoring in Photography with a focus on Fine Art and Social Documentary.