Born in Portland Oregon, Kaitling discovered her passion for acting at the University of Oregon, where she studied theater. After her stint on stage, Olson moved to LA to pursue acting professionally. She began at the Groundlings Theatre, where she secured a coveted spot in the Sunday Company. This proved to be a great showcase for Olson as it led to recurring roles on both Curb Your Enthusiasm, where she plays "Becky" the sister of "Cheryl" and the Drew Carey Show, where she played the role of "Traylor" the nemesis to the "Mimi" character. Olson also had the pleasure of joining Drew Carey's Who's Line is it Anyway? Improve troupe who performed regularly at the infamous Melrose Improv. This led to Olson joining Carey on a USO tour to perform for the troops in Bosnia, Kosovo and Norway.Soon after her stint on the Drew Carey Show, Olson was cast as a series regular on the Fox series Kelsey Grammer Presents: The Sketch Show.Previously, Olson was also cast as a series regular on the FOX improve Meet the Marks and recurred on The Jamie Kennedy Experiment. Other roles include guest starring with Alicia Silverstone on Miss Match and her recurring role on Punk'd where she led pranks on Amber Tamblyn and Beyonce.