Ishola obtained a Higher National Diploma (Insurance) from the Federal Polytechnic, Offa in Kwara State in 1998 and Associated Member of Chartered Insurance Institute of Nigeria with various Technical and Management Training.
He has worked in many organizations among which are Towergate Insurance Company Plc., Boof of Africa Insurance Brokers Limited and T.A. Braithwaite Insurance Brokers Limited from where he joined the Company in 2006 as Assistant Superintendent when her trade name was Industrial and Development Insurance Brokers Limited. Presently, he has over 22 years of experience in the industry.