Deep within the recesses of the DoubleTree Hotel in Pittsburgh, Jason Wolfe is mentally preparing himself to deliver a speech at his company’s quarterly meeting. He’s stationed in the back of the hotel’s ballroom, seated, swiping through slides, reviewing his talking points. He looks up, takes a breath, and begins to make his way toward the front. Wolfe, the 45-year-old chief executive of GiftCards.com, is hardly shy. But there’s always something a little unnatural about speaking to—and answering questions from—a hundred or so employees gathered in a single room.