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Olayemi Popoola has extensive work experience in various leadership roles. Olayemi currently serves as a Board Member at Invictus Africa, where they are involved in promoting human rights and gender equality through evidence-based advocacy. Prior to this, Olayemi was the Group Chief Executive Officer at Cloudware Africa, leading the company in its technology services. Olayemi has also served as the Board Chair at PlungeSmile Foundation, working towards bridging the gap between subsistence and poverty-induced livelihood. Additionally, Olayemi has held the position of Group MD/CEO at Reliance Infosystems, a global technology services organization with a presence in 21 countries.

Olayemi Popoola has a diverse education history. In 1991, Olayemi attended the University of Ilorin and obtained a Bachelor of Engineering (B.Eng.) degree in Electrical and Electronics Engineering in 1997. In 2014, Olayemi participated in the Owner Manager Program at the Lagos Business School, Pan-Atlantic University. In 2018, Olayemi attended the Harvard Business School for Executive Education in Disruptive Innovation. Additionally, in 2023, Olayemi obtained the Microsoft 365 Certified: Fundamentals certification from Microsoft.