Peggy Olson (Elisabeth Moss) started out as a secretary, spending her days typing and fending off unwanted advances. But by the middle of season 1, she was penning ads for Belle Jolie lipstick — and not long after that, she was officially promoted to Junior Copywriter. As season 6 begins, Peggy has left SCDP behind to become Cutler Gleason and Chaough's Copy Chief. Her trailblazing would pave the way for Megan Draper (Jessica Paré), née Calvet, who eventually became SCDP's second female writer. (Though in Megan's case, marrying the boss didn't hurt).