Pettengill started his career in radio at the age of 13 at a local radio station in Amsterdam, New York. In 1986, he hosted the morning radio show on the Albany, New York area's WFLY "Fly 92", called the Wake Up Service. It was the highest rated show in Albany history. Later on, he was promoted to program director and then vice president of Albany Broadcasting Company. Pettengill left the station for WIOQ in Philadelphia and eventually WPLJ in New York. He was the youngest morning show host in New York radio at the age of 25, when he became co-host of the WPLJ morning show with Scott Shannon, where he is known for his "phone scams". Pettengill and Shannon were seen on Dish Nation. Todd Pettengill has been named Billboard Magazine Major Market Air personality of the year six times and Radio and Records Major Market Air personality of the year four times. He founded Pettengill Productions, Inc in 1993 and 17Black, LLC in 2007.