Gottlieb joined Simon & Schuster in 1955 as an editorial assistant to Jack Goodman, the editorial director. At Simon & Schuster, Gottlieb became editorial director within five years and drew attention for the publishing phenomenon of ''Catch-22''.
In 1968, Gottlieb—along with advertising and marketing executives Nina Bourne and Anthony Schulte—moved to Alfred A. Knopf as editor-in-chief; soon after, he became president. He left in 1987 to succeed William Shawn as editor of ''The New Yorker'', staying in that position until 1992. After his departure from ''The New Yorker,'' Gottlieb returned to Alfred A. Knopf as editor ''ex officio''.
