Maj. Gen. Masiello, of Linthicum Md., was commissioned in May 1987 from the United States Naval Academy. After Basic School he reported to Flight School at Naval Air Station Pensacola. In October 1989, Masiello was designated a Naval Aviator and assigned to HMT-303 for UH-1N Fleet Replacement Training. Upon completion, assigned to HMLA267, he deployed to Okinawa, and subsequently to the Philippines in support of MAGTF(C) 4-90. Following MAWTS-1 Weapons and Tactics Instructor course, Masiello deployed with HMM-164 (REIN), 13th MEU (SOC), supporting Operation Restore Hope in Somalia. Post Amphibious Warfare School in May 1995, Masiello served at Officers Candidate School, and reported to HMX-1 in August 1995; served as UH-1N Division Head and Operational Test Director, Plans Officer, Assistant Operations Officer, Presidential Command Pilot, and Marine One Pilot. In May 1999, Masiello reported for duty as Staff Secretary to 1st MAW Commanding General, in Okinawa. In March 2000, he went to Naval Postgraduate School for advanced acquisition study, graduating with a Master of Science degree in Management, with "Distinction" and as a Rear Adm. McClellan Award for academic excellence recipient. From June 2002 until May 2006, Masiello served as VH Assistant Program Manager for Systems Engineering and as Deputy Program Manager, Presidential Helicopter Replacement (VXX/VH-71) Program in Presidential Helicopters Program Office - PMA261/274. In May 2006, reassigned to V-22 Joint Program Office (PMA-275), he served as MV Deputy Program Manager and Director, Weapons Systems Integration until August 2007. He then reported to National Defense University, for the Senior Acquisition Course at the Industrial College of the Armed Forces. He served as Deputy Program Executive Officer, Air ASW, Assault and Special Mission Programs for Operations from June 2008 through July 2009. Masiello served as V-22 Joint Program Manager, PMA-275, from August 2009 to July 2013. He served as Senior Military Assistant to Under Secretary of Defense for Acquisition, Technology and Logistics, from July 2013 to August 2014. From August 2014 to November 2015, he served as F-35 Joint Program Director of Follow-on Development. In November 2015, Masiello assumed the role as the Assistant Commander for Logistics & Industrial Operations, Naval Air Systems Command. Masiello assumed his current position as the Program Executive Officer for Air Anti-Submarine Warfare, Assault & Special Mission Programs, PEO(A), in May 2018. Masiello's awards include: Defense Meritorious Service Medals, Meritorious Service Medals, Air Medal, and Navy and Marine Corps Commendation Medals, inaugural recipient of MCAA Michael Hough Acquisition Officer of the Year Award in 2005; FY2005 DoN Competition and Procurement Excellence Team Award Recipient; 2011 David Packard Excellence in Acquisition Team Award recipient; 2012 American Helicopter Society Harry T. Jensen Award; and FY2013 Dr. Somoroff DoN Acquisition Excellence Team Award Recipient.