Inside Gap CEO Richard Dickson’s plan to get another legacy brand back on its toes

Richard Dickson hit the pink carpet at the London Barbie premiere last July wearing a blush-toned suit and magenta pocket square. He smiled for cameras with producer-star Margot Robbie and writer-director Greta Gerwig as fans—some of whom had been lined up in Leicester Square since 3 a.m.—looked on. The event was a capstone of sorts for Dickson, who as Mattel’s then president and COO had helped transform Barbie from an outmoded feminist lightning rod into an icon of diversity,...