Roger Kiefer II serves as Chief Flight Instructor and holds an Airline Transport Pilot (ATP) certificate. A seasoned Captain in King Airs and Hawker jets, he also brings valuable entrepreneurial experience from building and running multiple successful businesses. Whether mentoring a first-time student or training the next generation of flight instructors, Roger’s genuine passion for aviation and commitment to excellence shine through in every lesson.

I’m a CFII/MEI with experience in more than 40 aircraft types, including extensive time in Bonanza and Baron aircraft. I enjoy working with a wide range of students—from new instrument pilots to experienced aviators—and tailoring my approach to how each person learns best. My goal is to help you become a safe, confident pilot while making the process both effective and enjoyable.

I have been at Stein’s Aircraft Services for the past two and a half years as a line technician, and I have been a CFI since August 2025. I’ve always wanted to be a pilot, but I almost pursued a career in law and graduated from Marquette University in 2023 with a degree in political science before ultimately deciding that flying was what I truly wanted to pursue. I love being a CFI because I had amazing instructors throughout my own training who helped shape the pilot I am today, and I enjoy passing that same encouragement on to my students. Watching them succeed and gain the confidence to fly has been one of the most rewarding experiences of my life. I’m so excited to fly with you!

I’m a United States Marine Corps veteran, bringing a structured approach to flight training. I am a CFI / CFI-I with abundant experience teaching students to become flight instructors and pass on the skills necessary to explore the skies. I have a wide range of experience flying light sport / complex / high performance / multi engine aircraft and can help you navigate your path through an aviation career or hobby. Throughout my life experiences I have learned that enjoying what you do is the most important thing. Training should be purposeful and progressive, but most importantly it should be enjoyable. Let’s fly!

Ever since I can remember I dreamed of flying. After 2 discovery flights prior to high school I was hooked. Attending the University of Dubuque, I got my double major in Aviation Flight Operations as well as Aviation Management. Upon graduation I returned back to Wisconsin where I completed my CFI rating through the accelerated course provided by Steins. After passing my CFI checkride I was hired by Steins in 2022. My favorite part of instruction is seeing the progression of students over the course of their training. With over 3 years and 750 hours of instruction given, I am still learning something new every single flight. I am excited to continue to learn more and continue to teach the next wave of future pilots!

I have had a passion for aviation for as long as I can remember. Since 2016, I have worked to turn that passion into certificates for Commercial Single and Multi engine aircraft, CFI, and A&P maintenance. I have experience with a variety of aircraft, including tailwheel and light sport. As an instructor, I aim to help students develop an understanding of aviation from propeller to tail and discover the joy the skies have to offer. There is nothing I would rather do than share the wonderful world of aviation with my students.

I’m an aviation enthusiast and a passionate flight instructor who enjoys helping students learn to fly with confidence and without unnecessary stress. I keep my teaching style relaxed, practical, and tailored to each student’s pace, focusing on building strong, real-world skills both in the air and on the ground. I’m qualified to instruct private, instrument, commercial, CFI, and CFI-I students, which has provided me with an abundance of experience training students during any phase of their pilot journey. Safety is always the priority—but I also believe learning to fly should be enjoyable, and I do my best to make every lesson both productive and fun.

I bring over 30 years of experience across engineering, project management, executive leadership, and consulting into my work as a flight instructor. My aviation background includes flying more than 25 aircraft types, with experience in vintage aircraft, warbirds, and a particular appreciation for tailwheel flying. In my instruction, I focus on helping students understand the flying environment, manage risk effectively, and make sound decisions in the cockpit. My goal is to help each student become a safe, capable, and knowledgeable pilot who can make the most of what aviation has to offer, and have fun!