John Fox
Currently John Fox is the head coach of the Chicago Bears. He also coached the Carolina Panthers and the Denver Broncos, and he won an NFC Championship and an AFC Championship, respectively, but lost both of his coaching appearances in the Super Bowl. Fox is just the second head coach in the history of the NFL to win four straight division titles since joining a new team.
Jon Gruden
Let’s see, Jon Gruden was the head coach of the Oakland Raiders and the Tampa Bay Buccaneers. He won Super Bowl XXXVII in 2003 in his first year with the Buccaneers (defeating the Raiders, who had traded him to Tampa Bay the previous off-season). And at the time, Gruden was actually the youngest head coach ever to win a Super Bowl at age 39 years, 5 months and 9 days!