One of the realities of contract flying is that, long before a pilot ever steps onto an aircraft, there’s paperwork, payment, and tax structure sitting quietly in the background. If that foundation isn’t set up correctly, it creates friction for pilots, operators, and flight departments alike. Until now,
My Conversation on the LD Aviation Podcast I recently had the chance to sit down with Lindsay Dyer for Episode 91 of the LD Aviation Podcast: The Future of Pilot Staffing. Lindsay and her team at LD Aviation are some of the sharpest schedulers and dispatchers I’ve worked with.
I didn’t grow up around aviation. I wasn’t one of those kids who lived at the airport or knew what a VOR was before middle school. The first time I flew an airplane was in the military. Everything I learned about flying—how to think about it, how
One of the things we’ve always believed at Flying Company is that the best pilot networks already exist. They’re just informal. Text threads. Phone calls. “Hey, are you free next Tuesday?” conversations. Quiet referrals between people who trust each other. We decided to build that behavior directly into
In flight operations, most friction comes from one simple problem: people having the right information, but not in the same place, at the same time. Pilots want to understand the mission before they commit to it. Operators want to know the crew fully understands the plan. Dispatchers end up relaying
Every flight department, charter operator, and insurance broker asks the same question when a pilot is proposed for a trip: “Are they qualified to fly this aircraft?” The answer to that question has traditionally lived in scattered documents. PDFs emailed back and forth. Old spreadsheets. Training certificates. Insurance questionnaires filled
If you’re a contract pilot, you’ve probably lived the same pattern for years. A trip pops up through a staffing firm. You get a text or email. You send a rate. Someone asks for your Pilot History Form… again. You dig through old PDFs. You send documents. Then
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
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
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