Upon graduating from Duntroon in 1982, Caligari was assigned to the
Royal Australian Infantry Corps and was posted to the
1st Battalion, Royal Australian Regiment (1 RAR), an infantry unit that his father, Barry Caligari, was commanding at the time. In January 2009 he was appointed Deputy Commander, Joint Task Force 633 – Afghanistan, as part of
Operation Slipper, a position he filled for six months. For his "distinguished service" in both of these roles, Caligari was appointed an
Officer of the Order of Australia in the
2014 Queen's Birthday Honours. Promoted to
lieutenant general in October 2014, Caligari was appointed
Chief Capability Development Group (CCDG) in succession to Vice Admiral
Peter Jones. In this role he was responsible for the Department of Defence's Capability Development Group; the branch tasked to develop and gain government approval for future defence capabilities. After ten months in this role, Caligari retired in August 2015 as part of a Defence restructure that necessitated cuts to senior management. His position of CCDG was identified as redundant at
'three-star' rank level, and has been scaled down. ==Personal life==