Kelly Leonard

Vice President of Creative Strategy, Innovation and Business Development - The Second City

Kelly Leonard is the Vice President of Creative Strategy, Innovation and Business Development at The Second City. His book, “Yes, And: Lessons from The Second City” was released to critical acclaim in 2015 by HarperCollins and was praised by Michael Lewis in Vanity Fair who called it “ excellent guide to the lessons that have bubbled up in Second City’s improv workshops.” Kelly is a popular speaker on the power of improvisation to transform people’s lives. He has presented at The Aspen Ideas Festival, The Code Conference, TEDx Broadway, Chicago Ideas Festival, The Stanford Graduate School of Business and for companies such as Coca Cola, Microsoft, Twitter, Memorial Sloan Kettering and DDB Worldwide. Kelly co-created an initiative with the Center for Decision Research at the Booth School at the University of Chicago, The Second Science Project, that looks at behavioral science through the lens of improvisation. He also hosts the podcast, “Getting to Yes, And,” for Second City Works and WGN radio that features interviews with academics, authors and leaders such as Brene Brown, Adam Grant, Michael Lewis, Lindy West, Dan Pink and Amy Edmondson.

For over twenty years, Kelly oversaw Second City’s live theatrical divisions where he helped generate original productions with such talent as Tina Fey, Stephen Colbert, Amy Poehler, Seth Meyers, Steve Carell, Keegan Michael Key, Amy Sedaris, Adam McKay and others. In 2019, Arts Alliance Illinois awarded Kelly and his wife Anne Libera with their Creative Voice Award.