Jeff Charney

With his shaved head, affinity for temporary neck tattoos, and a ban on PowerPoint, Jeff Charney believes in the power of the unexpected. "People want to take a walk on the wild side," he says. "But how do you get them to go there? You have to let people be comfortable in their own skin first, especially in corporate America." He's done it this way.

When Charney joined Progressive from Aflac almost two years ago, at his first meeting, he grabbed empty beer bottles with labels that read COMPLACENCY, GOSSIP, and ME, ME, ME and smashed them with a bat.

Charney sent a local high-school marching band through company headquarters, hired a gospel choir to break up a meeting, and had his new spokescharacter, the Messenger, ride a Harley down the hallway.

A field trip brought employees to an unfinished building to throw paint-filled balloons at the walls.

The results: Charney and his team have brought fresh ideas to the iconic Flo campaigns--one reason that Progressive wrote more policies than ever last year, more than $15 billion worth.