Mr Osoba is the CEO and Managing Partner of Dare to Dream Sports Management Limited, a sports marketing and management company. Dare to Dream Sports Management Limited also owns 49% of Igbajo United, which plays in the Nigerian National League, the second tier of Nigerian football, and 50% of third-tier BYT Academical FC, which plays in Nationwide League One.

Omobolanle Osoba has been involved in the development of some Nigerian players in Nigeria and Europe, including Nigerian U-20 international Adams Olamilekan in Remo Stars, Israel Ayuma of NK Istra 1961 in Croatia, Emmanuel Olugbe of Songdal in Norway, Emmanuel Ekpeyoung of Orgyte in Sweden.

Omobolanle Osoba has also arranged talent identification programmes with European clubs like Hammarby, training camps with Ajax Amsterdam in Holland in Nigeria, and trial opportunities for Nigerian talents with clubs like Olympik Donetsk in Ukraine, Academica de Coimbra in Portugal, and Masr FC in Egypt, among others. He has also consulted on Nigerian players for scouting departments and coaches in Africa, Asia and Europe.

Omobolanle Osoba is also the brain behind the Dare to Dream Project, proudly sponsored by UBA Group, one of the biggest banks in Nigeria, and Bigi Cola drinks.