In this episode, Lindsay Dyer speaks with Tyler Flagg, CEO of Flying Company. Aiming to bring greater transparency, efficiency, and reliability to pilot staffing, Flying Company is a platform built to streamline how flight departments find, evaluate, hire, and pay professional pilots. They address many of the pain points involved in the process and how Flying Company aims to alleviate the entire process, as well as changes they are looking to implement in the future.
Find more at: https://flyingcompany.com
Show Notes
0:00 Intro
1:14 Aviation Background
7:58 The Flying Company
17:27 Scheduling & Dispatching
19:49 Credentials & Communication
25:00 Safety Reports & SMS
30:09 Looking to the Future
35:49 Before Starting on App
39:35 Trusted Partner Program
41:50 Payment & Final Thoughts
ABOUT TYLER FLAGG Tyler Flagg is a former U.S. Air Force Special Operations Instructor and Evaluator Pilot and deployed Squadron Commander, with operational flying experience spanning 67 countries across six continents. During his final deployment, he led 35 Airmen and commanded a fleet of Special Operations aircraft in the Pacific theater.
After separating from the Air Force in 2021, Tyler transitioned into business aviation as Chief Pilot and Aircraft Manager for a Part 91 flight department in Arkansas. In that role, he experienced firsthand the operational friction and inefficiencies associated with sourcing, vetting, and compensating qualified contract pilots.
Motivated by that challenge, Tyler founded Flying Company, a platform built to streamline how flight departments find, evaluate, hire, and pay professional pilots—bringing greater transparency, efficiency, and reliability to pilot staffing.
Tyler currently serves on the NBAA Domestic Operations Committee and is an active member of the working group for NBAA’s Military Connect program, where he continues to support the transition of military aviators into civilian and business aviation roles.
Email: tyler@flyingcompany.com https://www.linkedin.com/in/tylerflagg/ https://www.linkedin.com/company/flyingcompany/