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Gbenro Dara has a diverse work experience. In 2021, they were the Founder/CEO of Octamile Inc. From 2019 to 2021, they were the Managing Director of Olist by Opera, a Marketplace and Classifieds. Gbenro was also a Fellow at On Deck, a platform for connecting the world's top talent. From 2017 to 2021, they were the CEO of Cheki, an online cars Marketplace in Nigeria. From 2016 to 2017, they were the Managing Director of Efritin, a classifieds platform in Nigeria. Gbenro was also the Chief Revenue Officer at Hotels.ng, Nigeria's largest online travel agency. From 2014 to 2016, they were the Co-founder and Chief Operations Officer of AutoGenius. From 2012 to 2014, they were a Founding Team Member and Head of Operations at Startup Partners Africa GmbH. Gbenro was also a Founding Team Member and Head of Content and Production at Jumia Nigeria. Lastly, from 2011 to 2012, they were an Analyst and Private Equity Fellow at Kaizen Venture Partners.

Gbenro Dara obtained an MBA in Business Administration and Management, General from Lagos Business School, Pan-Atlantic University between 2010 and 2012. Gbenro then obtained a BSc in Insurance from the University of Lagos. In 2013, they obtained an ACIIN (In view) in Insurance from the Chartered Insurance Institute, Nigeria. Gbenro is currently pursuing a course from the Financial Reporting Concil of Nigeria. Gbenro also holds certifications in Valuation and Corporate Mergers from KPMG (obtained in June 2012), Certificate in Insurance from CIIN, and a Diploma in Insurance from CIIN.