Masiello started his career at Venezia, he made one Serie B appearance before moving to Lumezzane (Lega Pro Prima Divisione).
In January 2006, he was involved in the transfer deal of David Di Michele, to join Udinese along with Pepe and Nicola Santoni in joint-ownership.
[4] In June 2011, Bari acquired Masiello outright and sold Paulo Vitor Barreto back to Udinese.
Press reports in August 2011 stated that he was involved in a plate-throwing incident at a Bari team dinner.
Fellow Bari player Alessandro Crescenzi was reportedly struck by the plate and had to have 40 stitches in the resulting wound.