After graduating college, Dippold started a career in improvisational comedy at Upright Citizens Brigade Theatre (UCBT) in New York City. She wrote and performed in various stage shows at the UCBT in New York City and still continues to perform improv on stage at the UCBT's venue in Los Angeles. She is a part of improv groups "The Smokes" and "Reuben Starship". Dippold has appeared as a Sketch regular on Late Night with Conan O'Brien and was a cast member on the MTV comedic prank series Boiling Points. In 2006, she became a Writer for the twelfth season of MADtv and was also a co-producer during its fourteenth season. In 2009, she joined the writing staff of Parks and Recreation where she worked for several seasons.