Allison worked at various positions for the famed comedy theatre The Second City in Chicago from 2016-2022. Allison joined the touring company in 2019 after showcasing for Lorne Michaels at iO Theatre in Chicago. During the 2020 pandemic, Allison left the touring company and became a staff writer for the Second City's corporate and theatrical arms of the company. Her last project with them was "The Revolution Will Be Improvised" which had a run in DC's famous Kennedy Center.