[1] She began her career appearing in Off-Broadway productions and guest-starring roles on television series including Law & Order and 30 Rock.

[1] Her film credits include Mother of George (2013) starring Danai Gurira, Poltergeist (2015), The Incredible Jessica James (2017) and The Light of the Moon (2017).

In 2015, Heyward was cast in the leading role alongside Sharlto Copley and Eddie Izzard in the PlayStation Network's first scripted original series, Powers.

In 2016, she co-starred in the HBO period drama series, Vinyl playing the role of personal secretary to Bobby Cannavale's lead character.

[3][4] From 2018 to 2019, Heyward played the role of Tamika Ward, the new Warden in Litchfield prison in the Netflix comedy-drama series, Orange Is the New Black.