A native of Jacksonville, FL, Commander Kohlskelley graduated from the University of South Florida in 2008, earning a Bachelor of Arts in Criminology. CDR Kohlskelley was commissioned through the Naval Reserve Officer Training Corps Program and reported to NAS Pensacola, FL for flight training in April 2009. He earned his Naval Aviator Wings in January 2010. In February 2010, CDR Kohlskelley reported to the HSM-40 “Airwolves” for initial fleet training as an SH-60B pilot.

CDR Kohlskelley began his first operational flying tour in November 2010 with the “Vipers” of HSL-48.  While a “Viper”, he made two deployments aboard USS FORREST SHERMAN (DDG 98) and USS VELLA GULF (CG 72), participating in various multi-national exercises and BMD operations in the Mediterranean and Black Seas.

CDR Kohlskelley reported to the “Airwolves” of HSM-40 as a Fleet Replacement Instructor Pilot in 2014, and served as the Quality Assurance Officer, DLQ instructor pilot, and FCP program manager, and was voted NHA Region 3 instructor of the year award for 2017. In August 2015, CDR Kohlskelley began studies in a Master of Business Administration Program at the University of Florida, graduating in December 2017.  In February 2018, he reported to “Team Factory” of CVW-8 serving as the assistant operations officer until March 2020.

CDR Kohlskelley returned to the fleet as a Department Head in HSM-77, the “Saber Hawks”.  While with the Saber Hawks, he completed three deployments aboard USS RONALD REAGAN (CVN 77) and USS SHILOH (CG 67) in support of 7th Fleet Freedom of Navigation operations, Operation Enduring Freedom, and Operation Freedom’s Sentinel serving as Safety, Training, OIC, and Operations Officer.

Following his Department Head tour, CDR Kohlskelley served as an action officer, Joint Staff, J-3 Directorate in Norfolk, VA.  While on the Joint Staff, he directly supported the Secretary of Defense Orders Book and the Global Force Management Allocation Plan, coordinating Air Power, Aviation, and ISR forces.  He selected for squadron command in March 2023 and reported to HSM-37 as Executive Officer in July 2025.

CDR Kohlskelley has accumulated over 2,600 flight hours in the SH-60B, MH-60S, and MH-60R. His awards include the Defense Meritorious Service Medal, Navy Commendation Medal (3 awards), Navy/Marine Corps Achievement Medal, and various service awards and ribbons.