A spotlight on First Officer Kevin Rosengren and his career change to chasing his dreams at Air Wisconsin

Two years ago, I was sitting in an office working as the Chief Operating Officer for a Product Management Consulting firm. Today, I’m living out my childhood dream as a 48-year-old First Officer for Air Wisconsin. This is the story of how I got here and why Air Wisconsin was the right choice for me.

In the summer of 2022, my family and I took a “bucket list” trip to Africa. We love to travel, and it was much needed family time following a few difficult years. Together with the trailing impacts of the pandemic, and amid the natural beauty and history of South Africa, I found myself reflecting on how quickly life goes by, and the knowledge that tomorrow is never guaranteed. It was transformative. When we returned home, my wife and I decided it was time to turn my long-cherished dream of flying for a living into a tangible reality.

My fascination with flying dates back to as early as I can remember. My formative childhood memories were filled with looking skyward for airplanes and family trips to our local international airport for what my parents called ‘free entertainment.’ In middle school, I traded my time washing and waxing a family friend’s plane for valuable flight hours. By 14, I took my first flying lessons and like many of my colleagues, soloed at 16 and proudly earned my Private Pilot’s certificate by 17. 

Despite my passion for flying, my initial education and career choices were more, well, grounded. For over 25 years, I had the privilege of enjoying a fulfilling career in Product Management and Consulting. This path provided the freedom and resources to pursue my passion for flying in my free time. Over the years, I steadily continued to learn and earned additional ratings while my total time approached that important 1,500-hour milestone. And yet, from time to time the lingering thought would surface – what if I was a flew for a living?

Shortly after making the firm decision to change careers, I began researching airlines. Like the finance and operations guy, I’d been for more than two decades, I started researching several regionals to help decide which one may be the right airline for me. In fact, I built a spreadsheet to compare options, and Air Wisconsin rose to the top of the list in several dimensions.

In October 2022, I applied, interviewed, received a CJO and ultimately a class date from Air Wisconsin. In January I was to report to Appleton for Indoc training. I was finally going to achieve my dream and become an airline pilot. 

Looking back at the last year, I wanted to share some of my views and experiences which reinforced why I think Air Wisconsin was the right choice for me and my family. 

Culture
My good friend and airplane partner, Captain Rob Cahill, joined the Air Wisconsin team in 2019 and had terrific things about the culture. He was not only an influence in my decision-making process but also a mentor as I began life as a First Officer. Shortly after arriving at our Appleton headquarters for training, I experienced the strong sense of the “Air Wisconsin family” he and others have spoken about. 

FO Kevin Rosengren and Capt. Rob Cahill

That family feeling was immediately experienced on my second trip flying the line. Carol Brennon was our Flight Attendant, and I had the privilege of being on her final trip before retiring after over 40 years with the company. From our Crew Resources manager sorting out her final trip, to our Captain coordinating celebrations, to the many people who stopped and hugged Carol as we walked through the airport. It left a very strong positive impression on me that I won’t quickly forget.

We are a relatively small airline, and you get to know people across the company quickly. I feel like I’m known as “Kevin” and not just by my ID number. That goes a long way when you need to reach out to someone for help or to simply answer a question.

Finances & Stability

With nearly 60 years in business, Air Wisconsin has an impressive track record of stability. As a bit of a financial nerd, one of the first things I did researching potential new airlines was to review publicly available financial reports. With a strong stockpile of cash and liquid assets, the strength of our balance sheet demonstrated the strategic soundness of the business, and that really appealed to me. My sense was that we are going to be sticking around for a very long time. 

Quality of Life (especially as a commuter)

Our contract, and especially with the newly ratified updates, is strong. Beyond the parity of the new pay scale, we have some excellent commuter provisions which surpass the competition. As a commuter with a family (including two teenage boys), the ability to manage the logistics and expenses associated with getting to work were particularly important to me. I’m especially grateful for several clauses that include between 3-6 commuter hotels per month and two-day Long Call. Both of those help me better be able to plan when and how I get to work, when needing to commute several states away. 

FO Kevin Rosengren and FO Aaron Holmes

Training
I believe that our training is top notch and is recognized as such throughout the airline industry. From Indoc, to systems, to our simulator training, our instructors are some of the best in the business. Several colleagues have moved on to other airlines and experienced other training departments. Each time, they have confirmed my experience; our training is some of the best of the regionals. It is not easy, but if you trust the process, follow the leads from the instructors, and do your part studying, there is no doubt that you will be successful. 

Getting Involved

Beyond just flying, I have found many additional opportunities to get involved with Air Wisconsin following my first anniversary with the company. I recently joined an ALPA committee to continue to support our pilot group and have proudly represented our airline at recruiting events across the country. It’s been very rewarding talking to young pilots just starting out in their career, seasoned pilots considering new opportunities, and pilots like me who are making the change and realizing a long-held dream.

FO Kevin Rosengren and Captain Mari Bales

So, there you have it; my story as a new First Officer at Air Wisconsin. It’s been a great first year and I’m confident that I have made the choice. I hope to see you on one of our flights soon. I’ll be the one on the flight deck, sitting in the right seat, probably with a grin from ear to ear.  

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