In 1977, Pessina took over his family's pharmaceutical wholesaler (possibly Petrone Group) in Naples, Italy, and turned it into Alliance Santé, a Franco-Italian pharmaceutical wholesale group. In 1997, it merged with Alliance UniChem. From 2001 to 2004, he served as its CEO. He served as deputy chairman, and later as chairman. The company merged with Boots Group PLC in 2006 and was taken private in July 2007. Pessina was chairman of Alliance Boots from 2007 to 2014 and currently serves as Executive Vice Chairman and Chief Executive Officer. Pessina is a director of Walgreens Boots Alliance. He is a director of the Consumer Goods Forum.