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Jon Fleschler has a diverse work experience spanning over several companies. Jon started their career at FTI Consulting in 2005, initially as an intern and later as a Research Associate. During this time, they analyzed client data, created queries using Access, and organized client data to improve efficiency. In 2008, they joined Crowe Horwath as an Information Security Consultant, where they provided written deliverables for information security assessments and performed network security assessments for various organizations. In 2009, Jon joined Fairway Independent Mortgage Corporation as a Software Developer, where they developed a web portal and integrated an Electronic Document system to streamline processes. Jon then returned to FTI Consulting in 2011 as a Consultant, where they were responsible for database development, data modeling, and developing custom applications to streamline analysis. Finally, in 2013, they joined Broadleaf Commerce as the Director of User Experience.

Jon Fleschler began their education in 2004 at Indiana University, Kelly School of Business, where they obtained a Bachelor of Science degree in Business with a focus on Computer Information Systems, Business Process Management, and Operations Management. In 2007, they participated in a Study Abroad Program at the University of Adelaide. Jon continued their academic journey by pursuing a Master's degree in Computer Science at The University of Texas at Dallas from 2013 to 2016.