Olusegun started his early education in Ogun state Nigeria, and proceeded to Ahmadu Bello University for an advanced-level preliminary course and later to the University of Jos, where he obtained a Bachelor of Science (Hons) in Business Management. He started his career with CGEE Financial Services, where he worked as a credit officer and rose to the post of head of credit and marketing in 2013.

In the advancement of his career, Olusegun took up a Masters of Science degree in International Finance (Corporate Finance) at Anglia Ruskin University, Cambridge, England, and later returned to Nigeria to put his acquired academic knowledge to work.

He briefly worked for Gifthings Concept Nigeria, an IT and business solution company, before joining Cititrust Financial Services Ltd, a subsidiary of Cititrust Holdings Ltd., where he worked as a business Analyst.

He joined Capitalfield Investment Group Ltd as Group Business Analyst in January 2020 and has since then steadily added value to the businesses of the Group.