Oladejo moved to Canada in 2001 at 16. Initially interested in law, she found her passion for acting while working at the Canadian Opera Company. After studying theatre arts at Humber College and the Soul Pepper Academy in Toronto, she struggled to find roles and almost gave up acting. Following her agent's advice, she submitted a self-made casting video and landed the role of Joann Owosekun on Star Trek: Discovery. Since then, she has appeared in various theater productions, including roles in Shakespeare's Hamlet and Chekhov's The Cherry Orchard.