Commander Penn is a native to Chesapeake, Virginia. He enlisted in the Navy and graduated basic training in Orlando, Florida in 1992. He was then selected for Aviation Aircrew Candidate School and Aviation Rescue Swimmer School in Pensacola, Florida. He reported to Fleet Replacement Squadron, HELANTI-SUBRON ONE in Jacksonville Florida for Aircrew flight training in the SH-3.
Upon graduation of the FRS he reported to HELANTI-SUBRON FIVE in Jacksonville Florida. He made two deployments on USS GEORGE WASHINGTON (CVN -73) in 1994 and 1996, and one on USS JOHN C. STENNIS (CVN 74) in 1998 for an around the world cruise in support of Operation Deny Flight, Southern Watch, and Enduring Freedom. A graduate of the Helicopter Weapons and Tactics school at NSAWC in Fallon, Nevada he served as a Weapons and Tactics instructor for the SH-60F and SH-60H in 1998.
He then selected for the Enlisted Commissioning Program, attended the Naval Science Institute in Newport, Rhode Island, and then reported to Jacksonville University Naval ROTC unit as an Officer Candidate. He graduated magna cum laude from the University of North Florida earning a Bachelor of Arts in History. He entered flight training and earned his wings of gold in NOV 2002.
He then reported to the Bear Aces of VAW-124 where he served as the Ground safety Officer, Flight Schedule Officer, Aircraft Division Officer, NATOPS Officer and Landing Signals Officer. He deployed in OCT 2005 onboard the USS THEODORE ROOSEVELT (CVN-71).
In FEB 2007, he reported to Fleet Replacement Squadron VAW-120 for duty as a flight instructor in the E-2C Hawkeye. He served as the Operations Admin Officer and Aircraft Division Officer.
He was selected the Flag Aide in SEP 2009 for the Commodore, Strike Force Training Atlantic. He had the privileged to serve for RDML Gary R. White and RDML Dennis E. FiPatrick.
In OCT 2010, he reported to the United States Naval War College and earned a M.A. in National Security and Strategic Studies.
He reported again to the Bear Aces of VAW-124 as a Department Head in NOV 2011. There he served as the Admin Officer and Maintenance Officer.
CDR Penn was then assigned to Cruise Missile Support Activity Pacific, United States Strategic Command, Joint Force Component Command Global Strike J-7, as Director of Tactics and Training, responsible for evaluating all Navy TLAM planning cells and integrating them into STRATCOM operational plans.
CDR Penn arrived in Iwakuni, Japan August 2017 as Executive Officer of squadron VAW-125 The World Famous Tigertails, and was promoted to Commanding Officer in January 2019.
CDR Penn has accumulated more than 2500 mishap-free flight hours and over 300 carrier-arrested landings in the E-2C Hawkeye.
His awards include the Defense Meritorious Service Medal, Navy Commendation medal (3), and Navy Achievement Medal (2), as well as several other personal, unit, and campaign awards.