After working as a stand-up Comedian, Grandy turned to television writing and became a Writer on Jon Stewart's The Daily Show in 2001. After his Daily Show stint, Grandy became a Writer and Producer on Saturday Night Live, where he worked until 2008. In the same year, he joined the writing staff of the fifth season of the American version of The Office. At the beginning of the sixth season he became a co-producer and by the time the show entered its seventh season, he had become a supervising Producer of the series. After the cancellation of his show, Guys With Kids, he joined his former Office cohort, Mindy Kaling, on the second season of her show, The Mindy Project, as a Writer and co-executive Producer.