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Kevin Flynn's work experience includes positions in various companies and industries. Kevin started their career in the US Navy as an Electronic Warfare specialist from May 1989 to February 1993. From 1992 to 1995, they worked in sales roles at Simple Distributors and teckno. Kevin then joined Marcus Evans as a Sales professional from 1993 to 1999. In 1999, they briefly worked as a Financial Planner at Madison Securities. Following that, they worked as a Broker at Brown and Company from 1999 to 2001. In 2001, they became a District Sales Manager at Celtic Insurance until 2002. Kevin joined optionsXpress in 2002, where they held various leadership roles - starting as VP Trading until 2010, then served as VP Account Services until 2012, and finally became Senior Team Manager, Client Development from 2012 to 2017. From 2017 to 2020, they worked as a Senior Manager Trading Solutions at Charles Schwab. Currently, they are working as a Senior Trading Operations Specialist at TradeStation since February 2021.

Kevin Flynn attended DePaul University from 1994 to 2000. No specific degree or field of study information is available for this period.