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Robert "Bobby" Kaminski's work experience includes being an Assistant Vice President of Risk & Data Management at Direxion since March 2023. Prior to that, they worked at Eze Software (SS&C Eze, a unit of SS&C Technologies) from 2014 to 2023, where they held various roles including Principal Engagement Specialist, Senior Engagement Specialist, Engagement Manager, and Analyst. Before that, they had summer internships at Tempewick Wealth Management in 2013, where they focused on estate planning, and at Complete Consignment in 2013, where they were responsible for listing merchandise on developing websites. Robert "Bobby" also had a sales and trading internship at Knight Capital Group in 2012. Robert "Bobby" studied at Delbarton School from 2007 to 2010.

Robert "Bobby" Kaminski pursued their education by attending Delbarton School from 2006 to 2010. Robert "Bobby" then went on to enroll at Bowdoin College from 2010 to 2014, earning a Bachelor's degree. During their time at Bowdoin College, Bobby focused their studies on Economics and Classical Studies.