Italiano started his coaching career at NSW NPL club Blacktown City where he held the position of sporting director, during which the club won the 2015 National Premier League NSW season and the National Premier League Finals.

[1][2] Following this success he joined A-League Men club Sydney FC where he would work alongside Graham Arnold, Steve Corica, and Ufuk Talay whilst working with the Sydney FC academy set up.

[3] When Ufuk Talay departed Sydney FC in 2019 as manager of New Zealand A-League Men club Wellington Phoenix, Italiano was one of the first people that Talay sought to bring across the Tasman Sea, which Italiano was initially hesitant to do.

[1] Italiano would join the Wellington based club as an analyst, before working closely with Talay, as he was announced to be an assistant coach for the Phoenix.

[4] As Italiano progressed through the club's coaching hierarchy, he completed his AFC Professional Coaching Diploma, a pre-requisite for managers to earn before they can become the head manager of a club in the Asian Football Confederation.