Cackowski began her comedy career at The Second City in Chicago where she was discovered and hired by Saturday Night Live, where she worked as a Writer from 2003 to 2006. Since leaving SNL, she and Maggie Carey created an online series called The Jeannie Tate Show.
Her surname is Polish. She is married to Akiva Schaffer, whom she met when they were both writing for the 2005 MTV Movie Awards.
She appeared in feature films such as Forgetting Sarah Marshall and I Love You, Man. She also co-starred as "Byte" in the Adult Swim series Fat Guy Stuck in Internet in 2008 and also starred as a housewife in another series called "Infomercials" in 2014. In early 2009, Cackowski wrote for the short-lived ABC sitcom In the Motherhood. From 2009 to 2010, she worked as a Writer and story Editor on the NBC comedy series Community. Her brother is Comedian Craig Cackowski, who has also appeared with guest roles on Community. She also wrote for the short lived NBC sitcom Up All Night. She wrote 2 episodes of 2015 comedy The Last Man on Earth on Fox.
She also played the role of Wendy, the realtor in the comedy movie Neighbors (2014), and in its sequel Neighbors 2: Sorority Rising (2016).
