Executive Director

Brooke Flanagan has served as Executive Director for Steppenwolf Theatre Company, America's premier ensemble theatre, since 2020. Together with Artistic Directors Glenn Davis and Audrey Francis, she is responsible for stewarding the company's artistic growth, programmatic service and economic vitality. During her tenure, the Tony-award winning theatre has expanded their artistic campus with the addition of the Lefkofsky Arts and Education Center and Ensemble Theatre in Honor of Helen Zell; produced/ presented myriad productions across their three stages in Chicago; and transferred work to Broadway, Playwright's Horizon and MTC (NYC), CTG and Geffen Playhouse (LA), and the Galway Arts Festival (Ireland). New plays premiered during her tenure include PURPOSE by Branden Jacobs-Jenkins, which is the only production in history to win the Pulitzer Prize for Drama, Tony Award for Best Play and Steinberg/ATCA New Play Award.

Prior to this role, Brooke served for ten years as Chicago Shakespeare Theater’s Managing Director, responsible for the theater's fundraising, strategy, and external affairs programs. During her tenure, she increased the theatre’s annual contributed income by 50% and led the $62 million Our City, Our Shakespeare Campaign. Key programs included: a rebranding/positioning campaign; Chicago Shakespeare in the Parks; Shakespeare 400 Chicago; and the opening of The Yard at Chicago Shakespeare.

She held early-career roles at Santa Fe Opera and League of Chicago Theatres as well as tenures as Associate Director of Development at Ravinia Festival and Director of Major Gifts at Steppenwolf.

Brooke has raised more than $300 million across the span of her career for non-profit arts organizations. She is a member of Economic Club of Chicago and The Chicago Network, a Board member of the League of Chicago Theatres and Arts Alliance Illinois (Past Chair 2016-2020). She served as a Mayoral appointee to Chicago's Cultural Advisory Committee (2021-2025) and during the Covid crisis, championed the Arts for Illinois Relief Fund, launched a mask fabrication program for out-of-work costume artisans, and served on multiple "back to work" task forces.

Brooke received the Nashville's Mayor’s Acts of Excellence Award for her direction of The Holocaust—a Gathering of Stones. She has been included in "Who's Who in Business" by Crain's 2023-2025. She resides in Lincoln Park with her husband and three children who proudly attend Chicago Public Schools.