Jessica's experiences across the theater world are vast and far reaching. For over five years, Jessica worked as a Lead Teaching Artist in Open Book’s Read​ Then​ Write Residency Program where she traveled throughout Chicago, teaching reading comprehension and creative writing to students in underserved communities.

Independent of Second City, Jessica has trained comedians in over 10 different countries including Lebanon, Greece, Poland, Germany, South Africa, China, and the Czech Republic and works as Education Manager for The Nursery Theatre in London.

As a facilitator, she leads corporate improv and idea generating workshops where she has enjoyed working with companies such as NetSuites, LinkedIn, and Willis Towers Watson.

Jessica is also a performer and director. She has directed more than 40 productions, including MY AMERICAN COUSIN at Silk Road Rising, VISPETTA: A COMMEDIA DELL’ARTE PRODUCTION at Italian American Theatre Company of Chicago, MEAT CUTE, and NOSTALGIA SUCKS: BUT IT USED TO BE AWESOME! Jessica was a participant in LaMama International’s 2017 Directing Symposium as well as The Lincoln Center’s 2018 Directors Lab. She is proud to have worked as Director for one of Second City’s National Touring Companies and as Assistant to the Director on the Mainstage production, SOUTH SIDE OF HEAVEN.

I AM A ZEBRA

Performance Art for Learning in the Worlds of Medicine and Healthcare

Originally from Youngstown, Ohio, Jessica Mitolo  is currently a director and teaching artist in Chicago, Illinois. As the current Associate Artistic Director and a faculty member at The Second City Training Center and Second City Film School, Jessica develops content and teaches improvisation and comedy writing to students of all ages and skill levels.


Jessica is partnering with I AM A ZEBRA, not only as coach and director for performance pieces, but as a facilitator in workshops focused on the use of performance art and improv skills as a way to support and enhance collaborative decision making in the worlds of medicine and healthcare: workshops with participants whose stakeholder roles are similar; and amongst stakeholders who hold different roles within and across those worlds.