About
Leadership doesn't come with a playbook, so I built one. Too many managers are setup to fail, not from lack of effort, but lack of support. Level 5 Manager gives you the tools to lead with clarity, confidence and make a real, lasting impact.
NICE TO MEET YOU
I'm Kyle Stephens
With nearly 20 years in aviation and transportation, I’ve built a career leading high-pressure operations while developing leaders and driving results. I’ve served as a Certified Flight Instructor, led airport and trucking operations, and managed teams of 100+ employees across multiple business lines. I believe the best teams are built through clarity, consistency, and a people-first culture—and I’ve seen that approach earn top honors, including the Safest Base in the World award at my current operation.


Real-World Experience
I've led teams in aviation, trucking and warehouses, building high-performing cultures in high-pressure environments.

Leadership That Delivers
From struggling teams to award-winning operations, I've built trust, developed leaders, and driven results.

Built For Managers Like You
Level 5 Manager exists to give you the tools, mindset, and support you never got, so you can lead with confidence from day one.


My Leadership Journey
From teaching students how to fly in the early days of my career to overseeing large-scale airport and trucking operations, I’ve learned that great leadership is never about the title—it’s about the example you set. As a General Manager, I’ve led multiple business units across fueling, cargo, passenger services, and ground handling. I’ve developed high-performing teams, turned underperforming stations into thriving operations, and coached countless employees into leadership roles of their own.
Outside of aviation, I helped scale a trucking operation into a +$1 million annual revenue business, building systems, leading logistics, and managing the people that made it work. Across every role, one thing has stayed the same: I lead by being visible, setting clear expectations, and building trust through action.

"Working with Riley has changed my life. I’m only 2 months away from debt-free!"
- Martin Marino

"Last year, I was 49 with no retirement savings. Thanks to Riley, I’m now financially on track."
- Bill Bayaud

"From buried in debt to living the life of my dreams, Thank you, Riley!"
- Susan Smith
Why IÂ Built Level 5 Manager
Too many new managers are thrown into leadership without a roadmap. I’ve seen great people struggle simply because no one showed them how to lead. I created Level 5 Manager to change that—to give leaders real-world strategies, practical tools, and the confidence to thrive in their role.
This isn’t about fluff or theory. It’s the kind of training I wish I had when I started. Whether you’re leading your first team or trying to rebuild trust in a struggling one, my goal is to help you become the kind of manager people want to follow—and the kind of leader you’re proud to be.

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