From Hospitality to Insurance: Kelli Kresowski Offers Her Take on Career Transitions, Mentorship, and Remote Work

By: | April 3, 2025

Kelli Kresowski is the Division President, SVP at AmRisc, LLC, the largest catastrophe-focused Managing General Agent (MGA) in the U.S. She initially joined AmRisc as an underwriting assistant in 2007, taking the role of online program manager in 2017, and promoting to Senior Management in 2020.. She serves on the Southeast Associate Board for Insurance Industry Charitable Foundation (IICF). Kelli can be reached at [email protected].

Topics: Risk Insider

Not every insurance or risk management career has a defined purpose. When I graduated from high school, I had no clear direction. Yet after working in the hospitality industry, first inside a hotel and then as a flight attendant for a regional airline, I learned that I enjoyed customer service.

As it turned out, the customer-facing skills I learned in those earliest jobs paved the runway for an exciting and rewarding career in insurance, and even an exhilarating cross-country move. None of this would have been possible without a well-timed referral from a friend and employers who were willing to embrace a young professional from a non-traditional career path.

Preparing for Takeoff

My insurance journey began almost by accident. In 1999, after two years as a flight attendant, the glamour of travel started to wear thin. Thankfully, I had a friend who ran a job placement agency. She suggested that I interview for a receptionist position at United States Aviation Insurance Group (USAIG).

To be honest, I did not see a huge connection between insurance and flight attendant work at the time. However, as I moved steadily from answering phones to agent billing to policy creation, I realized that the customer service and problem-solving skills I had learned in hospitality dovetailed perfectly into an insurance role.

Craving Growth

By 2002, I was ready to expand my horizons. I set my sights on Hylant (then Hylant MacLean), the largest insurance company in my hometown region of Toledo, Ohio. My interview went well, but the manager could not hire me because I was not licensed.

That moment brought me clarity. At that point, I did not even know I needed a license. To progress, I needed to get licensed and relocate to a city with greater opportunities. Eventually, I chose Houston. I packed my belongings (including my cat), found an apartment online, and arrived on a Wednesday. By Monday, I had secured a position with Hotchkiss Insurance Agency. Five years and a few career moves later, I joined AmRisc, where I have remained for 18 years.

Building Confidence

Throughout my career, mentors have helped me build my confidence. Whenever I encountered challenges while learning a new role, I would ask a senior-level manager for help, and they would coach me through the situation. I learned that they enjoyed sharing their expertise with younger workers, and my mentors became my biggest advocates as I moved through the ranks at AmRisc.

Outside of AmRisc, I participated in as many networking opportunities as I could find. Through organizations like the Insurance Industry Charitable Foundation (IICF) and Wholesale & Specialty Insurance Association (WSIA), I learned the insurance and risk management community is nurturing and supportive. IICF also allowed me to participate in multiple community service and charitable giving initiatives, showing me firsthand how people in our industry have the power to change lives within the communities where we live and work.

Recognizing and Leveraging Non-traditional Talent

As our industry navigates critical talent shortages, companies in insurance and risk management will need to continue opening doors to professionals with non-traditional career journeys. Hiring managers should assess candidates for risk management and insurance positions by not only their credentials, but also by the transferrable skills they bring, including their leadership potential.

At AmRisc, when we identify employees with natural leadership skills, we create new roles that align with their talents and offer avenues for promotion. For example, we actively recruit teachers. Teachers are curious, creative and willing to learn, three traits that make them invaluable team members. Many have transitioned into leadership roles, including Angela Matthews, our Chief Underwriting Officer and SVP for our Technical Risk Division. Watching Angela and other former teachers flourish in our industry is a pleasure and a privilege.

Additionally, we have found that many of our highest-performing employees at AmRisc come to us through referrals from family members. Our workforce includes brothers and sisters, dads and daughters, husbands and in-laws. Some employees even met here and eventually got married. Our approach to hiring family members brings multiple benefits, including low employee turnover rates and increased loyalty, with most of our employees working at AmRisc for a decade or longer.

Building a Stronger Future

To create a continuous pipeline of young talent, insurers should prioritize two essential areas: embracing remote work and creating a culture of giving.

Young professionals today expect flexible work options, and at AmRisc, our remote model helps us recruit aspiring talent across geographies. As we refined and matured our remote work model in the years since the pandemic, we have forged powerful new ways to work.

We continue using FaceTime exclusively for weekly video meetings. Sometimes we have a formal agenda, while other times, we use the hour to discuss weekend plans or personal milestones. These interactions help us bond as a team virtually without sacrificing the in-office “watercooler talk” that I believe helps create safe, comfortable spaces for all employes. Additionally, we host quarterly in-person meetings to strengthen our team dynamic further.

Along with remote work opportunities, younger employees also want to work for companies that give back. That’s where organizations like IICF bring immense value. Not only does IICF offer volunteer opportunities through annual events like the IICF Month of Giving, but they also provide regional summits and conferences that create networking opportunities and build a sense of belonging.

Early-career professionals seeking future leadership roles can get a head start by joining an IICF board, leading a committee or spearheading a volunteer effort. Then, they can share their experiences with others in their organization. Every time I talk about IICF at AmRisc, people want to learn more about it and are excited to get involved.

Creating Safe Landings for Others

My transition from hospitality to insurance was made possible thanks to friends who believed in me and mentors who showed me the way. In the same vein, I encourage our industry to light the path for other young professionals from non-traditional backgrounds. I would love to see more organizations reach out to junior and seniors in high school, because once young people know the amazing opportunities insurance can offer, I believe they will be inspired to soar throughout their careers. &

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