[3][4] She says that her parents have been a strong support system for her and that actors such as Angela Bassett and Will Smith were positive influences for her to pursue acting and comedy.

After three seasons of being a part of the main cast of Love That Girl!, it was announced that Webb had been upgraded to the leading role of the television series after former lead actress Tatyana Ali was prevented from returning due to contractual obligations to the now cancelled BET television show, Second Generation Wayans.

[7][8] In 2013, Webb was featured on a special showcase of Saturday Night Live that focused on female comedians of African American descent.

[10] Also in 2014, she had a recurring role in the ABC medical drama series, Grey's Anatomy playing Teresa Morris.

[14] In 2016, she appeared in the comedy films Ride Along 2 starring Kevin Hart and Meet the Blacks opposite Mike Epps.

In 2018, she appeared in the thriller Acrimony starring Taraji P. Henson, and had a supporting role opposite Kevin Hart and Tiffany Haddish in the comedy film Night School.