After coaching, he had a long career at Warner Communications (today WarnerMedia), where he developed the first cable television sports networks, pioneered interactive and pay-per-view television and events, oversaw and marketed the New York Cosmos soccer team, and produced for ABC and worldwide syndication Pelé's farewell game event (with Muhammad Ali and other celebrities). Later, new New York City Mayor Rudolph Giuliani tapped Sherman to become president of the failing New York City Off-Track Betting Corporation (OTB), which, within two years, Sherman made profitable for the first time while revitalizing its tawdry image.