Tyler is a former Special Operations pilot who has flew operationally in 67 different countries over 6 deployments. After separating from the Air Force he was the Chief Pilot for a Part 91 aircraft. Currently, Tyler is the CEO of Flying Company.
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If you’ve ever staffed contract pilots for a flight department, you already know the reality: most of the work happens before the airplane ever leaves the ground. Finding qualified pilots, comparing experience, verifying documents, confirming availability, handling payments, and keeping everything straight across emails, texts, and spreadsheets. Flying Company
I’m Tyler Flagg, a former special operations pilot and the founder of Flying Company. I built this platform after spending years in cockpits and operations rooms where finding the right pilot—or being recognized as one—was often harder than it should have been. Flying Company was designed to
If you’re an aircraft manager, chief pilot, scheduler, dispatcher, or part of a flight operations team—you already know this is a high-stress, high-stakes, relationship-driven job. The margin for error is small, the expectations are high, and the workload never really stops. Yet many flight departments still spend hours
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For years, the aviation industry has relied on a single blunt instrument to gauge pilot quality: flight hours. Hours certainly reflect experience, but they do not tell the full story of how a pilot will perform tomorrow, how they communicate in a cockpit, or how they manage workload during complex
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In aviation, professionalism isn’t measured in hours alone. A pilot can have 10,000 hours and still lack discipline or adherence to best practices, while another with 2,000 hours might demonstrate exceptional judgment, safety awareness, and a commitment to continuous improvement. The difference isn’t just in experience
In business aviation, a Pilot History Form is one of the most important—but least standardized—documents in the entire staffing process. Every insurance broker and every underwriter seems to have their own slightly different version. For contract pilots, this means constantly filling out new and often redundant documents in
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Business aviation has always relied on relationships, professionalism, and trust. For decades, flight departments have operated with limited visibility into safety behaviors, limited access to data, and almost no modern tools for evaluating contract pilots beyond “hours and a handshake.” Flying Company is changing that — not by replacing the human
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A New Step Forward in Safety & Professionalism At Flying Company, we’ve spent the past few months steadily raising the standards of safety and professionalism across the staffing process. What began with Professionalism by Design, which gave operators a clear way to identify whether pilots were operating as independent
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My Conversation on the Startup Junkies Podcast I recently had the chance to join the Startup Junkies Podcast for a conversation about aviation, entrepreneurship, and the unlikely role Northwest Arkansas is beginning to play in the future of aviation technology. What started as a simple interview became a great opportunity
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In business aviation, safety systems often depend on one thing: whether information can flow freely from the cockpit to the people responsible for managing risk. Too often, that flow breaks down. A stark reminder of this challenge appears in the NTSB’s final report on the 2014 Gulfstream IV accident
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Across business aviation, operators often rely on flexible staffing models by utilizing independent contract pilots. These contingent relationships allow flight departments to meet mission demands efficiently, but they also introduce important considerations for how those relationships are structured and represented. That’s why we’re excited to introduce an update
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Recently, I sat down with Simon Turner on the Chief Executive Aviator Podcast to talk about my journey — from growing up in a family of actors, to serving 14 years in the Air Force, to flying corporate jets, and now building Flying Company. It was a wide-ranging conversation, but at