Motorists Insurance Discusses Handling Role Changes, New Technology Trends and Organization Improvements

Motorists Insurance Discusses Handling Role Changes, New Technology Trends and Organization Improvements

John Kessler

SVP and Chief Strategy Officer

Motorists Insurance


Bryan Kaiser

Founder and President


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Hello, and welcome to the comSpark podcast, where you will get to meet today's technology thought leaders. To learn more, visit

BK: Hey there. We are here today with John Kessler, who is the Chief Strategy Officer at Motorists Insurance Group. Motorists Insurance Group is an organization based in Columbus, Ohio and focuses on property, casualty and life insurance in multiple states throughout the country. My name is Bryan Kaiser and I'm the Founder and President of Vernovis, also part of the executive host committee of comSpark, and I will be your guest moderator today. Let's get started. John, thanks for being with us. Uh, it looks like you've been with Motorists for about 34 years. So, in a time where the CIO’s role lasts 18 to 24 months, to what do you attribute your longevity, uh, with Motorists?

JK: First of all, Bryan, thank you, and it's a pleasure to be here with you. Um, you know, that first question is an interesting one because every time I, uh, meet new people and, and, uh, we share stories and they hear that I've been with the same company for my entire career, it's always, uh, it always generates an interesting reaction, because I'm kind of an anomaly in that way. But, uh, I've been with Motorists for 34 years, as you said, and, uh, came there right out of college as a programmer trainee, and it's just been, in short, it's been a tremendous organization that has presented me with all kinds of opportunities. So I, uh, through those 34 years, I kind of grew up through the proverbial ranks and I was Vice President of IT, uh, maybe since around ’02, and became the CIO, in uh, in ‘14. But I was the CIO for about seven years. And, um, I've recently transitioned from the role of CIO to Chief Strategy Officer. Could you repeat the question again, Bryan? What was the second part of the question?

BK: Sure. To what do you attribute your longevity?

JK: I think maybe what I attribute the longevity to is, number one, being part of an organization and an industry that has so much to offer. And so, while I didn't go to Motorists, didn't start at Motorists for the intent of staying there for 34 years, again, I've been presented so many opportunities. And so, that's been a big contributing factor. I think the other is just, um, I guess my leadership style. And it's just, it's been a good match for me. I ‘ve been well-aligned with Motorists. Um, being the CIO for seven years is unusual, as you say. Uh, but I think just recognizing that being with the same company has its pros and cons of being with the same company in that same role for that long. It has its pros and cons and recognizing that you know everything about nothing, uh, and leading with humility, I think, has been a contributing factor to me.

So, um, so throughout my tenure at Motorists and specifically throughout my tenure as CIO, I have really made an effort to continually learn and grow with the organization. Again, recognizing I know everything about nothing, uh, that, that means that I've had to do a good job and be very intentional about getting outside my comfort zone and spending time with other thought leaders, both within our industry and outside the industry, other thought leaders within this community, Columbus and Central Ohio. And again, just being intentional about continually learning and growing has been a, been a real contributing factor to me being there that long.

BK: That's great. I love that. And you know, you were the CIO for seven years, and then have recently kind of shifted into the CSO, Chief Strategy Officer role. So, I'm going to have an open-ended question here. How have you seen your role change as the CIO for those seven years, and then also as the CSO?

JK: It's been an interesting transformation, for lack of a better word. Uh, but I think early on in my career as Vice President of IT, and early on in my role as CIO, I think that role was very much operational or tactical. And throughout the course of time, uh, I noticed it starting to evolve to where it was much more operational and strategic. So, it wasn't necessarily the tyranny of “or,” but the power of “and.” That role kind of took on both of those components, tactical and strategic. And, um, throughout the course of time, as we grew through affiliations and merged with other companies, it became clear that we needed to make strategy more of a role in and of itself. And so, I've had the opportunity to let go of the operational aspects of the CIO role and take the strategic aspects with me in this new role of Chief Strategy Officer. And, uh, and that's really how it's evolved. And I think, um, as I reflect on not just how it's evolved at Motorists, but I see that happening really in a lot of other companies and a lot of other industries as well. They're starting to come up with roles like Chief Strategy Officer, Chief Innovation Officer, Chief Digital Officer. And uh, in reality, my role, my current role encompasses all those things. But that's really how it's, uh, like I say, transformed over the course of time. 

BK: That's great. I appreciate your insight there. So, how do you see technology changing in the next three years?

JK: Oh gosh. That's a, that's a great question. Um, what's interesting about that is that, I'm not supposed to answer a question with a question, but, how about you tell me? Um, because I, it's so hard to predict the future, and it's always been hard to predict the future in IT. And once upon a time, we used to put together plans that would go out 10 years, and then we pulled them back to five years. And now, if you have strategies and plans that go out three years, even that's a crap shoot, because things are changing so fast. As they say, the pace of change is exponential. And, so, how's it going to look in the next three years? I don't know. Uh, what I do know is it's going to be dramatically different than what it is today. And I think 12 months from now it'll look dramatically different than it does today. Uh, as we move more and more towards a shared economy, and with the impact of the internet of things and connected living, connected communities, uh, and in our industry, the advent of autonomous vehicles, all those things are going to not just change technology and change our industry, but it's going to change the way we live.

BK: Very true. And I, I could imagine as the Chief Strategy Officer, that is a big role. You're looking at a lot of different things along the way. So, how do you want to improve your organization in the next three years?

JK: Well, to stay on that thundering theme of technology and innovation, you're spot on. I, that is a big challenge for me and my role, and for our organization. Um, I think maybe the biggest impact I can have is to get our organization to a point where we can, um, respond to the disrupting technologies that are hitting our industry and our company. Uh, we can embrace innovation and make it really one of our core capabilities. Because, uh, I talked about, um, the pace of change being exponential. Organizations, for organizations to thrive and survive, we need to be in a position to respond to that kind of change.

Um, in our insurance industry and at Motorists, we are in the midst of a, of a heavy transformation as we transform our core systems. And I know a lot of companies have either gone through that already, that they’re in the midst of it, or they're just getting started. But we're about four years into transforming our core systems. And it's very important that we stay the course with that because what that'll do for us is, it, it'll lay down a new foundation built on modern technology, and it’ll position us to be much more responsive to those things I talked about earlier. I mean, I think words like transformation and disruption are overused at times, but there's no doubt there's technologies and changes that are disrupting our company and our industry. And in order for us to be responsive to that, we have to continue to transform the core and being positioned to ingest innovative ideas rapidly.

BK: So, open-ended question – in a professional setting, what makes you happy?

JK: I think, um, being in a role that, that gives you the opportunity to contribute to something larger than yourself. And maybe, back to your first question, Bryan – uh, that's, that's another, maybe, contributing factor to my longevity with Motorists. So, I've always felt like I've been given opportunities and put in roles to where I can really add value and really contribute back to the organization and contribute back to something larger than myself. I mean, you know, we talk about, at Motorists, we talk about, really, what our industry and what our company is all about is when, when bad things happen to good people, you know, we’re there. Uh, and so, to have that opportunity to contribute to a company that does that, fulfills that mission is what makes me happy.

BK: Uh, so last question here. As we wrap this up, who do you go to for advice?

JK: Um, a lot of people. I would suggest that, that's probably not atypical. That we all have trusted advisors, personally and professionally. Uh, so my dad has played a big role in my life, has been, in terms of being my hero and being a trusted advisor, all things personal and professional. So, I go to him quite a bit. I certainly go to my, my wife, Shelly. Um, it's interesting, because we've been together for almost as long as I've been at Motorists – 32 years. But, uh, she is my most trusted advisor, and it's always good to have somebody like that that you can go to and bounce things off, even professionally. And even though she is not in our industry and, um, she's a nurse by trade, she always has tremendous insight and then gives me invaluable advice.

And then, I think at Motorists, our CEO, Dave Kaufman is somebody who's been, uh, a leader and a trusted advisor for me for a good portion of my career. I always talk about how Dave is an easy guy to follow because he's a real energy giver. And maybe, to quote Abraham Lincoln, I would say I'm a success today because I had a friend who believed in me, and I didn't have the heart to let him down. And that person is Dave Kaufman. And so, I continually go to him on a regular basis for professional advice. And, uh, he's my personal mentor as well.

BK: That's great. I think this is an overlooked area of a lot of people's professional careers and lives where, I think it's important to have a group of people that you can go to. And there's an old proverb that says there's wisdom in the counsel of many. And, when I hear your advisors and the people that you look up to and the mentors – they all are coming from different angles. So, you're getting different perspectives from different people. And I think that's really important. And, uh, I know we've recently met today and I can tell you're a really grounded and well-rounded guy. So, uh, folks that’s the end of our time today. This is Bryan Kaiser and John Kessler. To learn more about us, visit, and we'll see you next time.

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