Chicago has a well-earned reputation as a holding company town, filled with decades-old shops that traditionally operate inside the city’s looming skyscrapers. But Highdive is proving that a spunky startup can not only survive, but thrive, in the Windy City. The 4-year-old agency—which is a repeat Midwest Gold winner—is on a tear, racking up agency-of-record assignments from Jeep and Boost Mobile, while cranking out two of the best Super Bowl ads of the year, Jeep’s “Groundhog Day” spot and a Quicken Loans spot featuring “Aquaman” star Jason Momoa.

See all of the 2020 Ad Age Small Agency Awards winners.

The leadership team is filled with big agency vets, including co-chief creative officers Chad Broude and Mark Gross, who left DDB Chicago to start the agency. The agency’s name speaks to its attitude. “For us it represented taking smart calculated risks, being daring, doing daring work, and daring things,” says Gross, who logged 22 years at DDB. “It really was about that feeling you have as a kid walking up those stairs staring and looking over the end of the high dive.”

The agency’s Super Bowl ads created such a splash that new business inquiries poured in—and the 30-person shop it is now staffing up to handle the increased workload.

—E.J. Schultz