As a youth, she was educated in Nigeria, Switzerland, and England. She received a Bachelor of Fine Arts in theatre from Smith College.
She is known for her role as Hayley Shipton in Castle and Jackie Joyner-Kersee in the American Broadcasting Company television sitcom The Neighbors. Her name is pronounced "Tokes Awlahgoondohyay". Olagundoye made her screen debuts on both television and the big screen in 2002.
In an episode of the television series The Education of Max Bickford.
And in the film Brown Sugar later that same year. She appeared opposite Ruby Dee in an off-Broadway production Saint Lucy"s Eyes in April 2001, and in 2005 she cofounded the theater company Three Chicks Theatre, which produced Andrea Lepcio"s One Nation Under in 2008.
Olagundoye has guest-starred on Ugly Betty, Law & Order, Computer Society of India: New York, Switched at Birth, NCIS: Naval Criminal Investigative Service and Prime Suspect. Her film credits include A Beautiful Soul, Come Back to Maine, Absolute Trust and The Salon.
In 2012 Olagundoye was cast as a series regular in the American Broadcasting Company comedy series The Neighbors, playing the part of Jackie Joyner-Kersee until the series was canceled after two seasons in 2014.
She later had starring roles in the two television pilots: Feed Maine, opposite Mary-Louise Parker for National Broadcasting Company. And Amazon"s Salem Rogers, co-starring with Leslie Bibb. Olagundoye joined the cast of American Broadcasting Company comedy-drama Castle in 2015 as a series regular in the role of Hayley Shipton.