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Winston Reuning has a diverse work experience in the executive search and talent management fields. Winston started at Diedre Moire Corporation in 2010 as an Executive Search Consultant, where they specialized in conducting confidential, retained, and contingent searches for top-level positions. Their responsibilities included defining the search criteria, conducting thorough research, qualifying candidates, and presenting detailed descriptions of potential candidates to clients. In 2016, they became the Director of Talent Management and Organizational Development at the same company.

Reuning also had experience as a CEO at Wobble Studios, LLC from 2007 to 2009, where they oversaw the operations of the company. Prior to that, they worked as a Pharmaceutical Research Assistant at Diedre Moire Corporation from 2002 to 2003.

Winston Reuning began their education in 2003 at Montana State University-Bozeman. However, no degree or field of study information is available for this period. Winston then went on to William Paterson University of New Jersey from 2004 to 2007, where they obtained a Bachelor of Arts degree in Communications.