Elevate Your Leadership Game with Jill Wagner Kelly

Jill Wagner Kelly, Chief Distribution Officer at Grange Insurance, spent 30+ years moving sideways and up through underwriting, sales, and executive roles. She describes her path as a lattice, not a ladder, and emphasizes investing in people, explaining the why behind decisions, and building a personal board of directors to challenge your thinking.
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What truly makes a dynamic leader? One who inspires, one who encourages, and one also who challenges others to become their best. On today's podcast, I have the distinct privilege of interviewing Chief Distribution Officer of Grange Insurance, Jill Wagner Kelly. Now, Jill sits in the C suite today, but has served in numerous positions in leadership throughout her career. And we'll talk about authentic leadership, empathetic leadership, and also leadership that requires courage to have difficult conversations. You're going to love this episode. It's going to make you a better leader and your agency a better agency. Enjoy. Welcome to the Agent Leader podcast. This is the podcast for agency leaders to learn, to grow, to develop, and ultimately become their best version possible. My name is Brent Kelly. I'm your host. It's a pleasure to be with you on this episode. And I have an incredible guest today who not only do I respect at such a high level professionally, we're going to talk about some of the professional achievements and learnings and success paths and all the things that I think agency leaders can certainly benefit from, but also someone who I happen to know personally. I have Jill Wagner Kelly, and you may notice that that's a similar last name as my last name. Jill is not only the Chief Distribution Officer at Grange Insurance, and we're going to talk about some of the stuff that she does there in leadership and. But she also happens to be married to my older brother, so we do know each other that way. So, Jill, welcome to the Agent Leader podcast.
Thanks for having me. Glad to be here. How can I say no to a family member? Right?
Well, you know, I had to be persistent, you know, in my ways of things going on. But listen, I have had the benefit certainly, of, you know, being with Jill at events and family things over the years, and I can tell you, obviously, she's a fantastic human being and individual, just a person that you like. But we also do get the chance to talk a little bit about leadership and insurance when we have some time. And so I'm excited, Jill, to. To go deeper into some really important subjects of, you know, of agency leadership and your perspective, you know, being on the carrier side and what you've learned and what you're learning in terms of leadership. And so we'll. We'll take this probably a number of different ways. But I really want to start off just by asking about your role. You know, I said Chief Distribution Office Officer. Hopefully I have that right. So just start off with this, Jill. What's your role within Grange and how do you work with agencies across the country?
Well, it's it's chief distribution. A lot of times people think, what is that? And I've been asked that several times, what, what is that? And basically, I'm in charge of sales and marketing. So when you're in charge of sales and marketing, it's working with agency partners. That, that is my number one job. I'm, I'm that fortunate. I grew up in the underwriting world, so I've, I've, I've worked with agents my entire career. But when you're on the sales side, it's a whole different ball game than when I'm on the underwriting side. And it's actually a better fit for me than the underwriting side. So I work with our agency partners in order to grow, find solutions, find ways for our teams to work better together and ultimately get us, get both of us where we need to be.
Yeah, I, I love it. And there's, so there's some commonalities even what I do and working with agencies, although we have different, different approaches and things we're trying to accomplish. You know, one of the things that I want to hear about is your leadership journey. You know, and again, we've had some, some conversations off air, so to speak, on it. But, you know, from where you're at now, right in your, your executive leadership position, there's a lot of different ways. I think some people even, I think, oh, there's one linear path to, to maybe get to the spot, but it doesn't work that way. So if you would, you'll kind of share your story, your experience and what you've learned on this journey.
Yeah, it's, it's, it's funny, I've heard so many time that times that insurance kind of finds you. Not many people go to school to be in insurance and say, you know, I want to be an insurance someday. You know, sometimes it's in the family, so it happens. But. So right out of college, you know, I was recruited on campus to work for an insurance company as a personalized underwriter. And I'm thinking to myself, I don't even know what that does. I don't even know what an underwriter does. So I said to myself, I'll do this for a couple years and then I'll move on to what I really want to do. And that was so naive, such a naive statement as I didn't know anything about this industry. So now it's been 30 plus years. And I'm passionate about helping the younger generation see what it has to offer on the carrier side on the agency side and the reinsurance side. And in those 33 years, I was a PL underwriter. Then I was a field underwriter focusing on commercial lines and pharma. So I've been on a lot of farms then a commercial lines underwriting manager. And then during that time, I was fortunate enough to get my mba. And what I learned from that really was critical thinking. And we did a lot of business case analysis for all types of industries, not just insurance. So when I worked as an underwriting manager, I started writing white papers about differentiation and finding ways for agency to view my carrier as a partner and a reason for them to want to stay with us and put business with us. So I added risk management and program and niche business to my journey. So you could see that it's kind of a lattice. It's not a ladder. It was really a lattice move for me. So. So then I moved to a company called Integrity Insurance, where I was brought on as the VP of commercial lines. And three years later, my boss left, and I was blessed to lead Integrity as their president. And at that point, I was drinking from a fire hose. I'm thinking, what made me think that I could take on running this whole company? But what we were able to build together came from the first day that I was in front of. Of the associates, and I told them, you don't build a company. You build people and they build a company. And, you know, that became our mantra, and it has remained the single most important leadership decision that I ever made. You know, people rally around people when they know we're in it together. So we were also part of a larger organization in Columbus, Ohio, called Grange Insurance, which allowed me to be exposed to even greater scale opportunities, which transformed me into my current role as the chief distribution officer. So with risk comes reward. So along the way, my greatest assets became the people that wanted to be part of building something together. So I found allies, coaches, mentors, and I view my career as a lattice. Everything doesn't have to be straight up. I need my boss's job. It can be. I just. I'm. I want to learn something else, and I'm going to expand my role. And. And that's basically what. What got me into the role I'm in today.
That's such a cool story. I love that lattice and like, just picking up bits and pieces and nuggets everywhere you go, and you challenge yourself in different areas. My guess is, Jill, some of those things were uncomfortable along the way.
Oh, like, like I said, I'm drinking From a fire hose. I mean, I'm, I'm now sitting in front of a board of directors in charge of, you know, a large organization that I'm thinking, you know, how am I going to do this? And I should have been thinking about it more as, hey, if I surround myself with great people there, we'll, we'll get it done. We'll, we'll do it. And that's basically been my success. I will, I will land always on surround yourself with really good people.
Yeah, that's great advice. And you know, part of this too, that you know, the audience and we were talking about this, you know, agency leaders, there's, there's huge challenges. I always, I always joke, Jill, this probably isn't very funny, but I said, you know, leadership would be easy if it wasn't for the darn people. Haha. And the other thing too is that, you know, this is my belief and you know, that the number one role of leadership above anything else is to grow and develop your number one asset, which is your people. And you talk about that. It's about growing people and growing people. And I know, you know, for agent leaders, it's a challenge for a lot of people that, that we work with in the sense of they may have come from a sales background or someone else else and done a really good job and now all of a sudden they've got this responsibility and opportunity of leading other human beings. And one of the things that I know, again, we've had some conversations about this and then also as I travel around to different events and people say, oh, you know, Jill, I'm like, yes, I do. And one thing that often comes up in people that I've talked that surround you is Jill is very authentic and open to some of these things. And you know, I think so much we think about it's what you know, it's what you know, it's what you know. And there's importance to what you know and having acumen. But I think there's a different level of leadership when you be able to be authentic and vulnerable and really getting to know people and what they want. And I'll brag on you because you're good, but you've done a great job of that. Again, people that I've talked with that, oh, Jill really gets to know people. So how is that just that idea of authentic leadership, what does that mean to you? How do you embody that? Maybe share an example of areas where you've had that of authentic leadership?
Yeah, if I, if I look Back now and look at my leadership style. To me, it just feels like I'm being me. I don't come with a different face on when I'm working. It's just me. So I recognize that all my associates, all the people that I work with, they have lives outside of work. We all have issues, we all have families, we all have bills to pay. We just come to work and do two different jobs. Doesn't make anyone better. It just makes us different. So once people know you truly believe that and you it and you walk the talk, they trust that. The decisions I'm making, I use, I'm using data points for I'm informed. I maybe have different levels of information coming my way that they might not have access to. So I always start with the why. People may not always like the end result, but they can see why I was making the decision. I've made some really tough decisions. After Covid hit, we were not using our building in Appleton. If we had, even before COVID maybe 20 people in the building at any one time and you have an asset sitting there and you think, okay, well, how am I going to talk through my decisions that I'm making about selling this building so that everyone can when I only add little, a few people in there at any one time? So I started with the why. And as soon as I explained the why, it's a, It's a much easier journey for me. So it's, it's a frequent story I share is about a prior boss that on my last day of work asked me if I could be. If he could be on my personal board of directors. At the time, I had no clue what he meant. He had shared that he wanted to be part of my journey and if we could, if he could be a sounding board for me, he was all in. I mean, what, what kind? That's a great boss to me, in my opinion. So that was a turning point where I've built a personal board of director of people that give you a different perspective. So if you consider yourself the CEO of you and you consider how a board works for a company, then it makes sense that surrounding yourself with people who aren't like you, that have different viewpoints, they were raised differently, they see the world through a different lens that is different than your lens, then you have surrounded yourself with a mighty set of who want to be part of your journey. And it's pretty powerful. And I use it as one of the pillars when I coach a mentor. I mean, I really. It's the final piece of the five step process I take people through is who's going to be your personal board of directors because you're the CEO of you. And, and that has been, that has worked unbelievably well for me over the, through my career.
I, I. What a huge takeaway, Jill. Just because, you know, think about that. We, we talk just, you know, in our vernacular about and this is for producers and leaders about Me Inc. That you own your own company. I mean it's part of another company, but you've got to think like that. And we actually say one of the roles as chairman of the board. And now it comes to mind of well, who's on your board, right? And, and who's the board of directors. And again I'll speak for agency leaders and I know, you know those listening right now, you know, some of you are with larger organizations and agencies, some may be smaller of people that you have, but it, it can feel sometimes lonely at the top in the sense of okay, I'm here, like who's going to challenge me? And maybe you're not thinking that with ego or malice, but it's just the fact that you start to get caught in your own world. And so you know, Jill, to have that personal board of directors of hey, you know what, you might want to consider this or your head's getting a little big here or something. You know, I know for me and having mentors and coaches around me where you just kind of get on your way and you lack awareness and someone asked you a question and you go wow, I didn't even consider that. So have you had some example? I mean whether it's people you're mentoring a coaching yourself where there's been, I don't have to be a specific example, but just mindset shifts that happen by having a personal board of directors, I.
Think I'll, I'll share because I coach a lot of people and they're all different too as well. So when we get to this segment of surrounding themselves, I always the discussion is who's on your board of directors and why are they on your board of directors? Because that tells me, okay, what was your thought process behind it? So I was coaching someone who was in a certain area of the company and said here's who I'm going to have on my personal board of directors that's going to help me in my area. And it happened to be another male. And I said to this gentleman, have you thought about what it would you surround yourself with someone who he might have a different perspective than you do about that area. But if you. It was. It was a finance area. I said, but have you thought about including a female in your personal board of directors? Because how they look at the financial aspect of a company might be very different than how you do, or how a male might look at it, because you're already in that. But that's. You're already similar. Two guys are already similar looking at that. So maybe add a female to that, because they might look at it totally different, or they might have been raised different. I go deep into understanding, not telling them who should be on there, just questioning their thought process behind it. I had an associate that worked for me for a very long time, very, very intelligent man working for me. And he had a really small he was a.
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