Agent Profile: Success Is Evergreen for Growing Wyoming Account Executive

“I told myself I was never going to be in insurance . . . ever!”

Those were the famous last words of Bailey Nowak, CLCS, CISR, Account Executive for HUB International in Cheyenne, Wyoming, before she unexpectedly fell in love with the insurance industry.

Bailey was born a fourth-generation Nowak in the state of Wyoming, and for her, it was almost predestined that she was going to be the third-generation insurance professional in her close family.

“Growing up, both my grandmother and mother worked in claims for a large health insurance company here in Cheyenne,” Bailey said. “It seemed inevitable that I would follow in their footsteps. My mother, in particular, spent her entire 32-year career in claims, and eventually, it wore on her to the point of retiring. Seeing that exhaustion day in and day out gave me a negative impression of working in insurance. Later I learned it was a big misunderstanding of mine—but at the time, I scoffed at the thought of working in insurance.”

Raking in the Dough

Bailey was much more interested in sales and business, which was evident as early on as middle school. 

“By age 12, I was running my own company.”

The company, Mow Time Premier, was also a primer for Bailey on what was in store for her future.

“It all started from helping my neighbor keep her lawn tidy while she was away from Cheyenne. My dad thought I did such a good job that I should make it a job. He encouraged me to be an entrepreneur and start my own lawn care business. So here I am, just 12 years old, and my father brings home this big yellow monster of a lawnmower for me to launch my own business with. I was only four feet tall and couldn’t even see over it—he had to take the handlebars down before I could even use the mower. And on top of that, we had a trimmer, or a weed wacker, that was also as tall as me! So when my dad suggested I start my own business, I set the parameters for the conditions and told him, ‘If I mow and you do the trimming, it’s a done deal.’ He agreed, and needless to say, he was impressed with my negotiation skills.”

Fast forward five years to Bailey’s junior year of high school, and she was averaging around 40 lawns per week during lawn-mowing season. Even so, her business was not her top priority outside of her education—it was her school athletics.

“I was playing basketball and soccer by the time I could form sentences as a young kid. That continued throughout childhood and into high school and I began traveling more in and out of the state for tournaments and camps. But I suffered a debilitating injury, and that’s when I gave some serious thought to how I wanted to design my future.”

A major family factor influenced the plans Bailey made.

“I asked myself, ‘Is sports really what I want to do the rest of my life?’ Nobody in my family ever graduated from college, not even for an associate’s degree. So, I became determined to be that first person to get my degree in all four generations of Nowaks—even if I had to finance it myself.”

Crucial Conversations

She had saved plenty of money from Mow Time Premier to put herself through college, but it turned out Bailey didn’t have to use any of it. She received a handful of scholarships instead and first attended Laramie County Community College (LCCC), where she continued to build a foundation for her strong business acumen through Business Cohort, a program that provided a real-world corporate environment and lifestyle at the college. Business Cohort formed teams of about 10 students who took courses and worked on business projects together over a two-year period.

During this time, her marketing teacher became a beacon for Bailey and her Mow Time business.

“One day, my teacher asked me if I had given thought to limiting my company’s liability and making it an LLC. Since the business was still growing, I thought it was a great idea, and she coached me through the process until the fateful day when I showed up at the Secretary of State office to file my business.”

What happened that day set the wheels in motion to drive Bailey down her eventual career path.

“When I walked in, they asked me for proof of insurance for Mow Time Premier, and being a 19 year old, I was so naïve I actually laid down my personal auto insurance card and thought that would suffice. After she explained I needed general liability coverage, I abruptly did a 180 and called my dad, who asked me, ‘First and foremost, you didn’t give them your auto insurance ID card, did you?’

Bailey acknowledged being the butt of the joke, and they both had a good laugh over the visit. Her dad then recommended she call a family friend who happened to be one of the only commercial insurance agents in Cheyenne.

Her talk with the agent quickly flipped from purchasing insurance to selling it.

“The first thing I saw when I went in to talk with him was this flyer on his desk that said, ‘Career Opportunities with HUB International.’ After issuing me a policy for Mow Time, his attention suddenly turned to, ‘Have you thought about working for us?’ At this point I had just started my junior year at the University of Wyoming, and I informed him of my plans on earning a four-year degree. That’s when he asked me if I would like to do what he does for a living after I graduated, to which I told him, ‘Respectfully, that sounds terribly boring.’ All he said back was ‘Okay, but believe it or not, you’ll thank me one day.’”

And it didn’t take long.

Don’t Knock It Until You Try It

Two hours later, while on the back of her mower, Bailey got a call from the Chief Sales Officer (CSO) of HUB. Without talking insurance at all, the two conversed about her business, successes and challenges she had faced, and how she envisioned her future.

“At the end of the conversation, he told me he was getting ready to send me a letter,” Bailey recalled. “I asked, ‘A letter for what?’ And he told me it was a job acceptance letter to start working as a producer for HUB. I ran and told my dad, who couldn’t believe the news. ‘This has got too be too good to be true,’ he told me.”

Bailey called the CSO back and asserted that she must graduate college first. She negotiated starting the position six months from then when she was nearing the end of her college career.

In the beginning of January 2020, Bailey was finishing up her degree online and had her first week at HUB’s Cheyenne office. Almost immediately, Bailey buckled down and within two weeks got her property and casualty license.

“The chains were off at that point, and I was literally hitting the ground running, going out cold calling, prospecting, knocking on doors, and trying whatever I could to build my book.”

That’s when the pandemic hit.

“For a few months things were locked down, people were staying home, doors were closed, and I did not want idle time. I was so excited to have this new career and was very enthusiastic, so my superiors encouraged me to use the time to get some designations under my belt.”

Bailey earned her commercial lines coverage specialist (CLCS) and certified insurance service representative (CISR) designations, and by wintertime places were opening back up in Wyoming, so she returned to prospecting and building her book.

“It was recommended that I take on my first year as a generalist—to evaluate all the different industries we insure and see which one would be the best fit for me. After visiting and writing my first hospital system, I was hooked—I loved it! So I applied to work in our healthcare vertical, and surprisingly, I wound up being the only one in HUB’s mountain region working in that vertical because it was relatively new territory for our company.”

Now, after finding her home in the healthcare vertical at HUB International at age 27, the sky is the limit for Bailey, and she plans to take full advantage of time being on her side.

“It’s so fascinating working with hospitals and other healthcare groups. As a broker partner, we look to partner with our clients and focus on risk mitigation, and risk mitigation is the overarching objective for hospitals. I have this saying I go by: ‘When you walk into one hospital system, you’ve walked into one hospital system.’ Meaning, each hospital is unique and has its own obstacles. Whereas it’s their job to care for us, it’s our job to help protect them. And that’s not just getting them the insurance they need, it’s also looking at everything holistically—the risks, how to manage them, the claims history, the compliance and regulatory issues they’re facing, and so much more. HUB is so resourceful—I have a team of folks all over the country that helps assist our healthcare clients from simple tasks to complex solutions. It inspires me. So in the future, I’d love to build up our healthcare vertical team and even lead it. But for now, I’m learning, and that’s the beauty of this wonderful insurance industry—there’s always something new to learn, and you can’t teach what you haven’t learned—so check back in with me in five years or so and I’ll teach you a thing or two.”