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Shola Ajewole has a diverse and extensive work experience spanning over several years. They started their career as an associate at the law firm Weil, Gotshal and Manges in 2003 and worked there until 2007. In 2007, they joined Comcast Entertainment Group as a Counsel, where they stayed until 2009. At ABC Studios, they held the positions of Director of Business Affairs from 2009 to 2010 and later became Counsel/Associate Principal Counsel in the Legal Affairs department from 2010 to 2013. They then joined Fox Sports as a Director of Business and Legal Affairs from 2013 to 2014 before being promoted to Senior Director in the same department until 2016. In 2016, they transitioned to Fox 21 as the Vice President of Business and Legal Affairs and worked there until October of the same year. Currently, Shola Ajewole is employed at FX Networks, where they started as the Vice President of Business Affairs in 2016 and are currently serving as the Senior Vice President of Creative and Cultural Diversity since March 2021.

Shola Ajewole attended Columbia Law School from 2000 to 2003. The degree obtained and field of study are not provided. Shola's education history also includes attending the University at Buffalo, but no details regarding the degree or field of study are given.