Jim Kales

Jim Kales
CEO of Aspire


As CEO, Jim works with 200 dynamic team members and Aspire’s Board of Directors to craft strategies that guide Aspire’s ground-breaking enterprises.

Jim has dedicated most of his career to nonprofit (or “for purpose”) work, including serving as CEO of Big Brothers Big Sisters of Lake County, and as the director of communications for the United Way of Metropolitan Chicago.

Jim graduated summa cum laude with honors from Bucknell University, and received his Master’s in Public Policy from the Harvard Kennedy School. Jim lives with his family in LaGrange Park and is currently teaching his youngest daughter to drive. Honk if you see him!

What’s your biggest challenge – or opportunity?  Our biggest opportunity is that the Chicagoland community really is ready for our message that “Together, We’re Better”. More and more companies, schools and organizations want to include kids and adults with disabilities and want to partner with us. But the challenge is making sure we do this strategically and sustainably – our resources and time are limited, so we need to stay focused.

What’s something people may not know about you? One of my summer jobs was a DJ, on the Greek island of Naxos. (And I learned a lot of lessons, believe it or not, for my current job!)

How do you stay motivated? I work together with our team at three different Aspire locales in the city and suburbs, not in a “corner office”. Working in our inspiring, collaborative spaces, and getting to meet the many participants with disabilities and their families visiting us each day…how can you not be motivated!

How do you take your coffee? Gotta have my Aspire CoffeeWorks Bold Ambition in the morning. With a shot of soymilk. (Don’t tell Tony Dreyfuss from Metropolis Coffee about the soymilk!)

Describe Aspire’s culture in three hashtags. #teamwork #getinspired #notyourtypicalnonprofit