Orsi became assistant coach of Roberto Mancini at Lazio in 2002. He followed Mancini at Inter Milan two years later. He left Inter in 2006 in order to pursue a career as head coach. Initially rumoured as possible Arezzo coach in 2006–07, he was surprisingly appointed to a Serie A job on 21 March 2007 by Livorno chairman Aldo Spinelli in order to replace Daniele Arrigoni. He made his debut with a 4–1 home win to Catania on 1 April, leading his side to a mid-table finish in the 2006–07 Serie A season. However, a disappointing start to the 2007–08 league campaign resulted in only two points after the first seven matchdays, convincing Spinelli to sack Orsi on 9 October, making him the first coach to be fired in the season. He was called back at the helm of the "amaranto" on 28 April 2008, after Spinelli decided to dismiss Giancarlo Camolese from the team's head coaching post, but did not manage to save his club from relegation to Serie B.