Rob Shepherd

Rob Shepherd serves as a Baltimore-based Captain for Southwest Airlines. In addition to acting as pilot in command while operating revenue flights, Rob has responsibilities as a Standards Check Airman, instructing and evaluating line pilots, instructors, and evaluators in simulator and operational environments. He also serves as an Aircrew Program Designee, conducting airman certification and qualification testing on behalf of the FAA for Southwest.

Originally from Denver, Colorado, Rob spent twenty-five years as an Air Force pilot. His first tour was as a T-37 instructor and evaluator pilot, followed by service flying transport-category aircraft including the C-5 Galaxy, C-17 Globemaster III, and C-130 Hercules. Rob also served in three command positions, including overseeing his squadron’s mission change from C-5 to C-17 operations and leading a C-130 wing with over 1300 members.

Rob holds degrees in Computer Science from the U.S. Naval Academy (B.S.) and University of Idaho (M.S.). He joined the Severn Leadership Group as a Senior Fellow in 2014, serving as a mentor for several Fellows cohorts and a member of the Board of Directors. He completed the C.S. Lewis Institute Fellows Program, an intensive, community-oriented Christian discipleship program, has served as a mentor for the Fellows Program, and leads the Institute in Annapolis as City Director. He is a co-author of Mentorship Mastery: A Holistic Guide for Virtuous Leaders.

When not otherwise occupied, Rob enjoys cruising the Chesapeake Bay with his wife on their Ranger Tug Kairos, reading, and running. He and Mary Beth have two grown children and two granddaughters, who are the apples of his eye.

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