Madison Derby

Flight Instructor, Wisconsin Aviation, Inc.

Allendale, MI 49401

Certifications · Degrees · Memberships

Degree Davenport University - BBA Cert CFI (Certified Flight Instructor) Cert CFII (Instrument Instructor) Cert Private Pilot License Cert Instrument Rating Cert Commercial Rating

Her Story

About Madison

Madison Derby is a Certified Flight Instructor (CFI/CFII) and commercial pilot currently working in the United States as a Flight Instructor with Wisconsin Aviation, Inc. Based in Watertown, Wisconsin, she also contributes to operations across multiple locations, helping train and mentor the next generation of pilots. Her role combines hands-on flight instruction with oversight responsibilities in a busy flight school environment.

Madison’s aviation journey began at age 16 after a discovery flight introduced her to flying—an experience that quickly turned into a lifelong passion despite having no family background in aviation. She soloed near her 17th birthday and earned her private pilot certificate at 18. She went on to complete her aviation training at Northwestern Michigan College, earning instrument and commercial ratings, and later expanded her academic background with a Bachelor of Business Administration from Davenport University, strengthening her foundation in aviation operations and management.

Now in her mid-20s, Madison has built a career spanning flight instruction, operations leadership, and aircraft management. She has served as a director of operations and flight instructor, managed training programs, and overseen aircraft and instructor teams. In her current position, she balances teaching students in the cockpit with managing operational workflows and fleet coordination. Looking ahead, she aims to transition into charter and corporate aviation, with a long-term goal of flying business jets such as Gulfstreams while continuing to grow within the professional aviation industry.

Her Interview

Ten minutes with Madison

01What do you attribute your success to?

I attribute my success to dedication and persistence—consistently putting in the necessary study and preparation required for aviation, and continuously learning from supportive colleagues in the field.

02What advice would you give to young women entering your industry?

My advice to young women entering the aviation industry is that it is an incredibly rewarding and fulfilling career. I have found it to be a field where I rarely feel like I am “working” in the traditional sense, and where the community is both close-knit and highly supportive. Through aviation, I have met many great people and built meaningful friendships, both personally and professionally, and I truly believe it is a special industry that offers unique opportunities and connections for those who choose to pursue it.

03What are the biggest challenges or opportunities in your field right now?

The biggest challenges in my field include the technical demands of aviation, which require consistent discipline and thorough ground study, as well as the continued underrepresentation of women in what has traditionally been a male-dominated industry, even though I have found colleagues to be generally supportive and receptive. At the same time, there are strong opportunities for growth, particularly in increasing female representation in aviation and expanding access to roles within charter and corporate flying.

04What values are most important to you in your work and personal life?

The values most important to me in both my work and personal life are mentorship and representation, community support, dedication to continuous learning, and a genuine passion for aviation.

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