Monroe performed at The Second City, both on the Chicago and Detroit stages. In Chicago, she appeared in the 2004 revue Red Scare, directed by Mick Napier, where the character "Sassy Gay Friend" originated, and she would later appear as Desdemona in one of the character's online incarnations.
She has appeared in episodes of The Neighbors, Parks and Recreation, According to Jim, Hannah Montana, Maron, Modern Family ("Bad Hair Day"), Key & Peele and the web series Cowgirl Up. In 2010, she appeared in The Back-up Plan. In fall 2012, she appeared in Applebee's commercials with ESPN host Chris Berman. In 2014, Monroe began appearing in commercials for La Quinta Inns & Suites and E-Trade, with Kevin Spacey.
As of Fall 2017, Monroe has a recurring role as Mindy St. Claire on the hit NBC sitcom The Good Place, starring Ted Danson and Kristen Bell. Monroe's character, due to a question of point allocation, is the only character who is in "the medium place," neither "the good place" or "the bad place." This allows for Mindy to live a boring eternity as an ex-cocaine addict reading the same People magazine and watching movies on VHS.
