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Drew Cartwright has a diverse work experience spanning several companies and roles. Drew began their career at ELS Language Centers in 1988, where they served as the Vice President of Special Programs until 1998. Drew then moved on to New Horizons Computer Learning Centers, where they held the position of Director of Global Business Development from 1999 to 2006. Following this, Drew worked as the owner of Wallflower Productions from 2006 to 2008. In 2008, they started working at Online Trading Academy, initially as a Franchise Training Manager until 2010, when they were promoted to Senior Director of Training & Development. In 2018, they were further promoted to Vice President of Training and Development and then became the Vice President of Operations in 2020. Drew's roles at Online Trading Academy primarily involved overseeing employee training, support, and event management.

Drew Cartwright attended Texas Tech University from 1980 to 1982, but did not obtain a degree or study a specific field during that time. From 1982 to 1985, Drew Cartwright then pursued a Bachelor of Arts (B.A.) degree in Political Science and Government at The University of Texas at Austin. In 2018, Drew Cartwright obtained a certification on Managing Conflict from LinkedIn, offered by Fred Kofman.