Employee Spotlight
(5 Minute Read)

A conversation with Matt Chlebek, Managing Principal

We sat down with Matt Chlebek, Managing Principal at Ledgestone Milwaukee and got into the nitty-gritty of the insurance industry, how his approach has changed over time, and what the future looks like for risk management, cultural health and more.  

Matt, thanks for taking the time to sit down with us.

M: Of course! Happy to do it.  

Let’s start at the beginning—how did you end up in the insurance industry?

M: I was finishing up my junior year in college, and I got an internship at a brokerage based out of Dubuque, Iowa called Cottingham & Butler. They happen to be the number one brokerage for transportation in the country. Through that internship program I went through a sales training program that had me making calls and appointments on top of some research on the industry.  

Sounds like a great learning opportunity.

M: Absolutely! It was during that time that I really developed a passion for opening the door and working with businesses, and really learning more about their companies. It also helped that if you did well in the industry, it would allow me to make a decent living, and have a lot of freedom in terms of my lifestyle.  

So how did you transition from Iowa to Milwaukee?

M: I tried to decide whether I wanted to stay at Cottingham & Butler, but I decided to take an offer with an insurance broker just outside Milwaukee. Starting out wasn’t easy, but I hit the ground running and got licensed. Even though the first 6 months I didn’t sell very much I was learning and going through a training program and eventually everything started to click and I built a decent book of business for myself.  

What worked for you there in terms of a sales approach?

M: I will be honest with you, I was doing everything I could just to sell insurance. My goal was to get my foot in the door, quote their insurance and try to save them some money, and try to generate a relationship. It worked really well for me, but in retrospect it really was a high-volume approach. I was throwing a bunch of things at a wall and trying to see what would stick.  

It was around that time you were first approached by Ledgestone?

M: Yea like I said, my approach was working well for me, and I had built a good book of business in a short amount of time. In 2019, I met Austin (Ledgestone’s CEO) through a mutual connection and to make a long story short, after a year and a half or so of conversations I ended up making the transition to running a Ledgestone branch based in Milwaukee alongside my partner Javier.

What would you say was the selling point for you? What changed?

M: The vision behind it. Our goal was to revamp the traditional model of insurance. I was a part of that model, which basically quotes insurance and tries to win business. We wanted to ask the question “what can your agency bring to the table?” The main focus needed to switch from writing premium and generating revenue to really being a partner for the businesses we worked with.  

As far as what changed, pretty much everything. Our approach takes time, especially to generate the kind of trust and relationship you need to really partner with a business and be a part of their long-term success.  Another thing I would say was different is the way the organization runs as a true team. Previously, it was kind of all on my shoulders in terms of working with my clients and as one guy, I have limitations. Whether it is just my capacity to work with each client, or whether it is industry specific knowledge and experience. At Ledgestone the team works together to ensure our clients needs are met.

What does that actually look like?

M: Starting with the insurance side of things, there is a whole team on my side now, with experience on such a wide variety of issues. There is an awesome service team that has my back to assist my clients with anything they need to adjust on their policy and walk them through claims or other issues.

But where the gap really starts to show is in some of the other resources at our disposal. At previous agencies, if a client had issues with employee development or employee engagement I couldn’t really do much to help them, but now I have someone like Kevin Dill (Ledgestone’s Chief People Officer and Organizational Health guru) to help them through those challenges. If client’s safety metrics were in the bin, I didn’t have the access to a third-party safety company that I do now.  

Everything before I would really describe as transactional. I give you coverage, you give me your business. Now I can really describe myself as a true partner in my clients’ success.

With that change to your approach, I’m assuming your conversations with businesses have changed as well?

M: Yes absolutely. My calls to businesses often used to end with a quoting war where the business owner would take my bid alongside 5 other agents trying to quote their business. Today the conversation we are trying to have is a stark break from that tradition.  

We are trying to tell business owners—”Hey, we know insurance isn’t broken, or really your biggest concern. We want to help you address the issues that are actually impacting your success, and provide you with the resources to help your business truly thrive, all at the cost of just moving your insurance.”

How have business leaders responded to that?

M: The hardest part is really getting that first conversation. People are used to the traditional approach to insurance and we are kind of coming out of left field for them in a way. And we don’t want to hit people with a bait and switch saying we want to talk insurance and then hit them with the real issues.  

When we do get a conversation though, the response has been really cool to see. One example is a company that I have been trying to quote insurance for since I first joined the industry. I had very little success over the 3 to 4 years as I tried to talk to them. Recently, we got another chance at a meeting and initially, I saw the same body language I had seen since 2017—arms crossed, not really interested in another conversation on insurance.  

But as we were able to have a conversation about the issues that really matter like safety, employee engagement, and culture. But we were able to have a conversation about the issues that really matter: safety, employee engagement, and culture—that body language started to change. Their leadership was engaged and participating in the conversation and admitting that they had never had a conversation on those topics with their broker, and wanted to learn more.

There was buy-in.

M: Exactly. Not every conversation goes like that. Some people are really skeptical of anything new. But it is awesome when we get to see that aha moment, that lightbulb going off in their head when they realize they could be getting so much more from their broker for essentially the same cost.  

Someone once told me that if you want to sell anything, you have to believe in its value. Does that ring true for you as you try to take this new approach to the insurance industry and build relationships with companies?

M: It does. Having lived in the mindset where you really are just pressured to write premiums I have had to stop and slow down.  We are here to partner with leaders to transform their culture and drive long-term success and I really do believe that we drive so much more value than a traditional broker so it is becoming easier for me to put that passion into my conversations with business owners.  

I think 5 years from now I will look back and be able to say with 100 percent conviction that we found the chasm and built the bridge between the things that businesses struggle with and the solutions to their challenges.  

Obviously, businesses will have to buy-in to something relatively unfamiliar to them—what would you say to those people on the fence about having a conversation?

M: That’s a good question. I would say that if you give us a chance, we won’t come in and shove a sale down your throat. I really want to learn about your business and the challenges that you face. It takes time to develop that relationship. If you give me your time, I will show up and we will bring real resources and solutions and show you what we can do to help you thrive. I’m not here to make a quick sale, I want to be a partner in their success.

Here’s what you can expect from me. One, someone who follows through on what they say they will do. Two, patience with building trust over time. Three, someone who is going to go beyond what you have come to expect from an agent to partner with you and your organization.

We aren’t a one size fits all company, and our proposition won’t be for everyone, but the people who do believe in the proposition and buy in, we will truly deliver for.  

Insurance has left a bad taste in a lot of peoples’ mouths and that can be hard to overcome.

M: Absolutely. Insurance works and risk transfer isn’t broken, but the approach that we (as an industry) have taken towards it is. Let’s improve your organization from the inside out and let that move the bottom line, your insurance programs, your safety, your productivity and more.  

Many people are going to tune us out. But I have grown to be ok with that. I think I would want to leave people with this—different isn’t necessarily bad, but it takes time to get to know and we want the chance to let you get to know us.  

Couldn’t have summarized it better. Thanks for taking the time to talk to us Matt.

M: Absolutely!