Dupe Olusola babban jami'iar kasuwanci ce a Najeriya. Ita ce Manajan Darakta kuma Babbar Darakta na kamfanin karbar baƙi na Najeriya, Transcorp Hotels plc, reshen kamfanin haɗin gwiwar Najeriya, Transnational Corporation of Nigeria. A watan Maris na 2020, membobin kwamitin da ke akwai suka naɗa ta ta shugabanci Otal din Transcorp, wanda ya zama mace ta biyu da za ta jagoranci kungiyar. Kafin ya shiga Transcorp Hotels Plc, Dupe ya kasance Shugaban Rukuni na Babban Bankin United Bank for Africa (UBA) kuma ya shiga cikin jagorantar duk ƙoƙarin kasuwancin ƙasashe 23 na kasancewar ƙungiyar UBA. Ta taɓa yin aiki a matsayin Manajan Darakta kuma Babban Darakta na kamfanin aikin gona na Najeriya, Teragro Commodities Limited, reshen kayan abinci na Transnational Corporation of Nigeria Plc (Transcorp Plc). An nada ta kan mukamin a shekarar 2014. A shekarar 2015 a matsayinta na shugabar kamfanin Teragro, an sanya ta a cikin manyan Daraktocin Najeriya 10 na Kamfanin Ventures Africa. Dupe ta halarci Kwalejin Sarauniya, Legas, inda ta sami GCE O-matakan a 1991.