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Phil Gilbert is a tall man with a shaved head and wire-rimmed glasses. He typically wears cowboy boots and bluejeans to work — hardly unusual these days, except he’s an executive at IBM, a company that still has a button-down suit-and-tie reputation. And in case you don’t get the message from his wardrobe, there’s a huge black-and-white photograph hanging in his office of a young Bob Dylan, hunched over sheet music, making changes to songs in the “Highway 61 Revisited” album. It’s an image, Mr. Gilbert will tell you, that conveys both a rebel spirit and hard work.