Greg Kedzierski

Greg Kedzierski is the founder of Tailplane, a modern all-in-one flight school management platform. With 20 years of software development experience across agencies, startups, and large enterprises, Greg brought a fresh perspective to aviation operations software when he earned his private pilot license in 2019. What he found in the cockpit—and on the ground—changed the direction of his career.

Professional Background

Greg’s path to aviation software entrepreneurship combines deep technical expertise with firsthand experience as a student pilot:

• Software Engineer & Entrepreneur: Two decades building software across agencies, startups, and large enterprises
• Private Pilot: Earned his private pilot license in 2019, giving him direct insight into the student pilot experience
• Founder of Tailplane: Built a complete flight school management platform from the ground up
• Operator-Driven Development: Developed Tailplane module by module based entirely on real conversations with flight school owners
• Aviation Technology Innovator: Pioneer in modernizing legacy flight school management systems

Building Tailplane

Greg’s aviation software journey began when he noticed a striking gap: flight schools managing half-million-dollar aircraft with software that looked two decades old. His response was practical and deliberate:

• COVID Origins: Tailplane started as a contactless payments solution during the COVID pandemic
• Operator Feedback Loop: After talking to flight school owners, Greg pivoted from a point solution to a full platform
• Incremental Build: Expanded the platform module by module based entirely on feedback from real operators
• Integrated Platform: Unified scheduling, fleet management, student progress tracking, maintenance, and payments in one place
• Smart Integrations: Includes features like TAF weather integration inside the scheduling view and drag-and-drop rescheduling with automated notifications

Areas of Expertise

• Flight School Software: Deep expertise in the operational challenges facing modern flight school owners
• Product Development: Proven approach to building software products that solve real problems through continuous operator feedback
• Aviation Operations: Understanding of scheduling, fleet management, maintenance, and student lifecycle management
• Technology Integration: Experienced in connecting disparate systems into cohesive, user-friendly platforms
• Business Scalability: Designs software with growth in mind, helping flight schools scale without adding administrative overhead

The Tailplane Platform

Tailplane addresses the core operational challenges that flight school owners face daily:

• Scheduling: Drag-and-drop scheduling with automatic student and instructor notifications
• Fleet Management: Real-time aircraft availability and maintenance tracking
• Student Progress Tracking: Monitor student milestones, hours, and training objectives
• Maintenance: Integrated maintenance logs and airworthiness tracking
• Payments: Streamlined billing and payment processing built for flight school workflows
• Weather Integration: TAF weather data embedded directly in the scheduling view