Grégoire's first job was as a receptionist and assistant at an advertising firm. She was promoted to an account manager, but after three years of working in advertising, public relations, and sales, she decided to attend radio and television school, where she immediately knew, "I had found my calling". After completing her studies there, Grégoire got a job in a newsroom, writing the news ticker. A lover of culture, arts, and films, when she became aware of an opening at Quebec television station LCN for an entertainment reporter, she applied and was successful in obtaining the position. In addition to serving as an entertainment reporter for LCN's daily Showbiz segment, she contributed to segments on Salut Bonjour Weekend, Clin d'œil, and Bec et Museau for TVA, and hosted Canal Évasion's Escales de Rêves and Canal Z's Teksho. Grégoire also served as co-host on CKMF Radio's morning shows and contributed to Radio-Canada's Coup de Pouce. Additionally, she worked in the mid-2000s as a personal shopper for upscale department store Holt Renfrew.