She is probably best known for her role as Katherine, the stern president of Panhellenic, on the ABC Family TV series Greek, or for her recurring role on the ninth season of The Office as Esther Bruegger, a neighboring farmer's daughter who becomes Dwight's girlfriend. Kirkpatrick starred in the 2015 film Pink Grapefruit, which won the SXSW Grand Jury Award. She has played many other roles in film and TV, including Men at Work, Jennifer Falls, Don't Trust the B, and Chasing Life. She was one of the leads of the popular mockumentary web series Dorm Life, in which she played Courtney Cloverlock. in 2016, Kirkpatrick created a TV show for Comedy Central entitled Best-Seller, which she wrote with Saturday Night Live alum Dennis McNicholas. The show was produced by Olivia Wilde, Jessica Elbaum, Will Ferrell, and Adam McKay from Gloria Sanchez Productions. In 2017, Kirkpatrick created, wrote and directed Virtually Mike and Nora, the first virtual reality comedy series for Hulu, with collaborator Mike O'Brien. The first two episodes of the series played at the 2017 Sundance Film Festival. In a 2017 Forbes article, Kirkpatrick mentions virtual reality's ability to cause "spatial un-comfortability," and her aim to make the viewer the lead character of the story. Kirkpatrick studies and performs at the Upright Citizens Brigade theater in Los Angeles.