Pierson attended Mountain Pointe High School, where he started acting and performing in a short-form improv group. He went on to attend NYU, joining the Sketch comedy group Hammerkatz NYU in the fall of 2003. He worked as both assistant Director and Director during his 3-year tenure with the group. Pierson graduated from NYU's Dramatic Writing Department in 2007 with a degree in writing for television. He also made three brief appearances on NBC's Community, on which his Derrick Comedy co-star Donald Glover plays a main character, as a Greendale Gazette member.

Pierson was featured on both of Childish Gambino's "I Am Just A Rapper" mixtapes, contributing verses to three different songs, 49ers (Orange Shirt), The Truth (Goth Star), and Different (Feel It All Around). Pierson along with Nick Packard was also featured on Childish Gambino's "Assassins" from the 2008 Album "Sick Boi". He was also featured along with Amber Petty on Childish Gambino's "Starlight" from the 2009 album Poindexter. Childish Gambino is the rap moniker of his fellow Derrick Comedy member, Donald Glover. He is also credited with the story told during "That Power" on Childish Gambino's Camp.

In January 2012, Pierson appeared on the YouTube sketch-comedy show Let's Talk About Something More Interesting.

In 2014, Pierson had a brief cameo in Captain America: The Winter Soldier as Apple tech support.