Skillman was the commissioning commanding officer of USS New Orleans (LPD 18). He also commanded USS Ponce (LPD 15) and USS San Antonio (LPD 17). His major command was as commander, Amphibious Squadron 4.
Ashore, Skillman served as the lead ship maintenance action officer for the Maintenance and Modernization Division (N43) and as the Sea Shield and Surface Warfare Program analyst for the Director of Integration and Warfare Assessment (N70) on the staff of the chief of naval operations. He was the military assistant and director of operations for the deputy director, Naval Warfare in Under Secretary of Defense (Acquisition, Technology and Logistics), Portfolio Systems Acquisition and served as the executive assistant and naval aide to the assistant secretary of the Navy (Financial Management & Comptroller).
As a flag officer, his tours include deputy commander and chief of staff, NATO Joint Warfare Centre, Stavanger, Norway, commander, Expeditionary Strike Group 2, he established the Enterprise Support pillar as director in MyNavyHR and most recently, Director, Programming Division OPNAV (N80).
Skillman’s decorations include the Defense Superior Service Medal, Legion of Merit, Meritorious Service Medal, Navy and Marine Corps Commendation Medal, Navy and Marine Corps Achievement Medal and various campaign, unit and service awards.