Gilady enlisted in the IDF in 1975. He served as a field artillery officer in the Golan Heights in command and fire support positions, and participated in operations beyond lines with special forces and other units. In 1982–1984, he was the Commander of Battalion 334 deployed in Lebanon (First Lebanon War). Following his promotion to Colonel in 1988, he commanded the Field Artillery School (Shivta) and special forces. In 1996, Gilady was promoted to Brigadier General and was appointed Assistant Chief Officer of the IDF General Staff’s Planning Division of the Planning Directorate, where he was responsible for managing the IDF’s long-term planning, force build-up, and multibillion-dollar budgeting. Gilady was appointed Head of the Strategic Planning Division in 2001, where he led strategic planning, national security policy formulation, international diplomacy and regional negotiations. Working closely with Prime Minister Sharon in 2001–2004 (Second Intifada), he developed the Gaza Disengagement Plan as part of a long-term process between Israel and the Palestinian Authority. In 2005, Prime Minister Sharon appointed Gilady Head of Coordination and Strategy within the Prime Minister’s Office, to implement the Gaza Disengagement Plan.