On 11 September 2007, Pioli was unveiled as new head coach of Serie B club Grosseto, replacing Giorgio Roselli, who was sacked after three consecutive defeats in the first three league matches, and managed to lead the Tuscan minnows to an impressive mid-table finish in their first season in the Serie B. He then served as head coach of Piacenza for their 2008–09 Serie B campaign. In July 2009, he left Piacenza to join Sassuolo as new head coach of the "neroverdi".