After college, Robb and his wife, Emily Wilkins, moved to Atlanta to teach high school to inner-city children. They then moved to California to work in his wife's family's almond-growing businesses. Robb started a health food store when they moved to Trinity County called Mountain Marketplace. After running the store for ten years, he and his wife divorced and he moved with his children to the Bay Area to manage a small natural foods chain. His longtime friend, John Mackey, convinced him to come work with Whole Foods. Robb started working with the Whole Foods Market in 1991 in the Mill Valley, California store that he operated. He became president of the Northern Pacific Region in 1993, building the area from two to 17 stores. In the year 2000, he became the Executive Vice-President of Operations and then Chief Operating Officer in 2001. He became Co-President in 2004.