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Dylan Webb - Instrument/Multi/Tailwheel
Dylan joined Sheridan Pilots 307 in September 2025 after recently completing his Tailwheel endorsement and gaining a wide range of experience as a flight instructor across the Midwest and South. Originally from the Kansas City area, Dylan earned his bachelor’s degree in Geology before following his passion for aviation and completing his flight training in Kansas City, Missouri. Since then, he’s instructed in St. Louis, Missouri, and Baton Rouge, Louisiana, before moving to Wyoming to be closer to family and continue his instructing career here in Sheridan.
Aviation has always been part of Dylan’s life. His uncle flew for Bighorn Airways, and his grandparents were both commercial pilots and flight instructors who ran the Buffalo Air Service in Buffalo, WY; a flight school and charter business that served the region for many years. Growing up around that family legacy inspired Dylan’s own love for flying and for helping others learn to do the same.
At Sheridan Pilots 307, Dylan takes a calm and thoughtful approach to flight instruction, focusing on solid fundamentals, good judgment, and helping each student build confidence in the cockpit. He’s logged over 1,000 hours of total flight time and several hundred hours of instruction given. Above all, Dylan is passionate about helping his students reach their aviation goals while providing a safe and fun learning environment. We are lucky to have Dylan on our team and he is already gaining many students!