Masiello has held a variety of systems acquisition roles including principal contracting officer for surveillance and reconnaissance systems, weapon systems and test ranges. She was an assistant professor at the Air Force Institute of Technology and Executive Director for the National Reconnaissance Office Inspector General. She has also served several staff tours including Deputy Director of Plans and Programs, and Director of Contracting at two systems acquisition centers.
Masiello commanded the 95th Air Base Wing, and from July 2005 through January 2006, she deployed to Iraq as Principal Assistant for Contracting Forces in Iraq/Afghanistan. Her responsibilities included contracting and acquisition support to forces in both countries, security transition support in Afghanistan, and humanitarian relief following the Pakistani earthquake. Prior to her current assignment, she was Program Executive Officer for Combat and Mission Support.
Lieutenant General Wendy Masiello is married to Thomas Joseph "Tom" Masiello, a retired Air Force Major General. The couple have two sons, who are also in the Air Force.