Lifestyle Personal Lines the June 2026 issue

Jessica Jung

President, Oswald
By Chris Hann Posted on May 26, 2026
Q
Your twin sons are a pitcher and catcher at the University of Mount Union in Ohio. How did you raise two sons who grew up not only to be a pitcher and a catcher, but also good enough to compete at the college level?
A
We spent many, many days, nights, and hours on baseball fields. Ever since they were 3 1/2 years old, those boys have been in uniforms.

FAVORITE VACATION SPOT: “Oh, so many. I love traveling to Europe. I love Miami. Italy might be my favorite place.”

FAVORITE MOVIE: The Money Pit

FAVORITE ACTORS: Robert De Niro and Julia Roberts

FAVORITE MUSICAN: Zac Brown

FAVORITE AUTHORS: Patrick Lencioni and Simon Sinek

FAVORITE CLEVELAND RESTAURANT: Marble Room Steaks and Raw Bar

FAVORITE DISH AT MARBLE ROOM: Shrimp scampi

Q
Did they always want to go to the same school?
A
They did not set out to go to the same school. They definitely wanted to explore playing in college. I purposefully made them separate, think independently, take an assessment of who they are, because while they’re great ballplayers, Major League Baseball might not be their end game in life. So they need a life plan alongside of that.
Q
You were the first person on either side of your family to go to college. That’s a big deal. Tell me about that.
A
I enjoyed school. I enjoyed learning. To me, it was never not going to happen. I ended up choosing Fairfield University [in Connecticut]. It was by far the most expensive option. I was able to secure the loans, and I said, “I’ll be fine. I’ll find a great job, and loans can be paid off.” And so that’s what I did. Now, it took me 13 years to pay off my college education, but I love the career I’ve built and the life I have.
Q
What was your favorite class in school?
A
I always enjoyed history. In college I became a psych major. I started college as a bio major. I wanted to be a pediatrician since I was 10 years old. And then, as a freshman in college—I still, to this day, can’t tell you why—one day I passed out. I fainted in a lab. And then it kept happening. I needed a new plan!
Q
What made you want to study psychology?
A
I just think it’s fascinating, the emotional intelligence of understanding other humans. That is always a critical dynamic of anything working well. You can be the smartest person; it doesn’t matter if you cannot articulate, communicate, engage, collaborate. Effective communication is the common denominator in so many things that go well in any aspect of business or life.
Q
You said you were fascinated by what you called the art and science of leading people.
A
I have become more fascinated with that over the years. I’ve always been the person who felt I could outwork anyone, and that works for you until you get to a role and a span of control that is too big and you are out of seconds in the day. That’s when you have to learn how to work smarter, not harder.
Q
What are the three best things about living and working in Cleveland?
A
People actually care here. Leaders pick up the phone. People collaborate to solve problems. The art, science, healthcare, theater, and so much more make it a bit of a hidden gem. It has been a wonderful place to raise my family.
Q
What is something your co-workers would be surprised to learn about you?
A
I think people would be surprised to hear that I was going to be a doctor but started passing out and had to switch majors.
Q
What three words would your co-workers use to describe your management style?
A
Collaborative, driven, and engaging.
Q
If you could change one thing about the insurance industry, what would it be?
A
It is very decentralized. It seems like an awful lot of time invested with everybody trying to solve the same problem and spinning their wheels without solving the problem.
Q
What gives you your leader’s edge?
A
The art and science of leading people. I think I get people. I’m passionate about inspiring others to take things to the next level, and what it takes to do that successfully.
Chris Hann Associate Editor Read More

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