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2019 Break Out Awards, Midwest: Kaileigh Bowe

Posted On: Jun. 1, 2019 12:00 AM CST

Kaileigh Bowe


Vice president, marketing, senior underwriter

Highland Insurance Solutions LLC, a unit of WNC Insurance Services Inc.

Naperville, Illinois

Age: 33

Kaileigh Bowe’s previous career in sales and marketing prepped the Winnipeg, Manitoba, native well for a career in the insurance industry because relationship-building is at the heart of both vocations. A core focus of her job is mentoring the next generation of industry professionals, and she said she is excited to see how they will change the way business is done.

What is the No. 1 concern in your specialty?

I’m in the builders risk market. The market as a whole is at an interesting state. There’s a loss of capacity. I also think that within the builder’s risk arena, there’s a lack of expertise. A lot of really experienced folks will be retiring in the next five years. That’s a concern. We really need to focus on the development of folks who are new to the industry, and that’s what my focus in my current role is trying to ensure, that we’re building up the next generation.

What surprised you about the insurance industry?

How exciting it is. There’s a lot of career opportunity within the insurance industry. It’s an industry that’s not going away. It’s going to be around forever.

What is something most people don’t know about you?

Hockey fan. I used to play hockey because I’m Canadian.

What would you/do you binge watch?

Binge watching “The Office” for, like, the 10th time. It’s strange how I find a lot of relation between being in the workforce and watching that. I referenced (the show) in a meeting about an hour ago.

What is your favorite meal?

Steak. I go to a lot of meetings with clients, and it’s generally a male-driven industry, so I feel like if I didn’t like steak, I’d be in the wrong industry.


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