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Stephen Crossman has a diverse work experience spanning several industries. Stephen is currently working at CourseKey as the Chief Revenue Officer (CRO). Previously, they held the same role at SurePoint Technologies and was also the Vice President and Head of Sales at Rippe & Kingston (now SurePoint Technologies). Before that, Crossman worked at Bloomberg Industry Group as the Vice President and Head of Sales for the Legal Division/ Bloomberg Law, where they led sales efforts and managed regional operations. Prior to that, they were a Sales Executive at Thomson Reuters and Senior Vice President of Sales & Marketing at E.P. Executive Press & National Association of Stock Plan Professionals (NASPP). Crossman also worked at Thomson Reuters as a Sales Executive, where they focused on challenging the legal marketplace and providing innovative solutions. Earlier in their career, they were the VP of Sales at Iconic Distribution, Inc., leading sales strategy and developing brand awareness. Stephen also served as the Director of Corporate Sales and Marketing at Abt Electronics, where they built and managed the Corporate Sales Division.

Stephen Crossman earned a Bachelor of Arts degree in Political Science from the University of Iowa in 1991. Following this, they attended the Chicago-Kent College of Law at the Illinois Institute of Technology, where they obtained a Juris Doctor (JD) degree in Law from 1994 to 1997.