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Olaoluwa Awojoodu's work experience began in 2009 when they became the Chief Executive Officer of (CashEnvoy) Electronic Settlement Ltd. Olaoluwa held this position until December 2017. In 2018, they joined E-Settlement Limited as the Chief Executive Officer. Currently, Olaoluwa is the Co-founder and CEO of Yep!

Olaoluwa Awojoodu's education history includes completing a fellowship course at the Alibaba Business School in 2019. The course, known as the eFounders fellowship, focused on an unspecified field of study. Prior to that, from 2001 to 2007, Olaoluwa attended Obafemi Awolowo University, where they obtained a Bachelor of Science degree in Computer Science and Engineering.