8. Todd Krinsky
When you're a company looking to revisit an earlier era, it's best to have someone from that earlier era calling the shots. And it's even better when that person is a grinder who started from the bottom. Todd Krinsky got his start in the Reebok mailroom—cliché alert!—and worked his way up, eventually rising all the way to VP. He paid dues in the '90s and early '00s, working (and partying) with Allen Iverson, which makes him uniquely qualified to deal with AI today. Some things never change.