Tailplane Founder Greg Kedzierski on Flight School Operations
Who Is Greg Kedzierski?
Greg is not a typical aviation software founder. He spent 20 years building software across agencies, startups, and large enterprises before getting his private pilot license in 2019. That experience in the left seat changed everything. He watched a flight school manage half-million-dollar aircraft with software that looked like it was built two decades ago and decided to do something about it.
Tailplane started as a contactless payments solution during COVID. After talking to flight school owners, Greg quickly realized schools did not want another point solution. They wanted one platform that could handle everything. So he built it, module by module, based entirely on real conversations with operators.
What You Will Learn in This Episode
- How Tailplane handles scheduling, fleet management, student progress tracking, maintenance, and payments in one place
- Why Greg built Tailplane incrementally based on direct feedback from flight school owners
- How TAF weather integration works inside the scheduling view so you can plan your day at a glance
- How drag-and-drop rescheduling with automatic student and instructor notifications works in practice
- How Tailplane tracks student training progress, completion rates, and lesson history tied to your custom syllabus
- What the onboarding process looks like and how pricing is structured
- How Tailplane integrates with Stripe, Veriyon, and Flight Docs, with a public API for your existing tools
- What is coming next, including a course marketplace, website builder, and MRO integrations
Episode Highlights
The Technology Gap Greg Spotted
Greg noticed that flight schools were running complex, high-stakes operations on software that had not kept pace with the industry. That observation became the foundation for Tailplane.
Built Around Real Flight School Feedback
Every module in Tailplane exists because a school asked for it. Payments came first, then scheduling, and now a full operational layer is coming together in a major relaunch.
Scheduling Built for How You Actually Work
The scheduling view includes timeline and grid views, drag-and-drop booking adjustments, TAF weather overlays, multi-location support, and automatic notifications when bookings change. Squawks automatically block aircraft from being booked.
Student Progress Tracking That Actually Means Something
Instructors can see completion rates, weekly booking cadence, and where students are falling behind, all tied to your custom training program. If a student has been inactive, the platform surfaces it.
Payments Without the Headache
Tailplane works with Stripe for online payments with tap-to-pay support coming to the mobile app. Schools that prefer their own payment provider can still record transactions in Tailplane to maintain a single system of record.
Pricing That Works for Smaller Schools
Plans start just above $100 per month for up to five aircraft at one location. The mid-tier is around $250 per month for up to 15 aircraft and two locations. The top plan is $449 per month, with custom pricing available for larger fleets.
Connect with Tailplane
- Website: tailplane.com
- Email Greg directly: [email protected]
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