Jason Angus - Leading a High Growth Strategy

Jason Angus

Episode 242: June 5, 2025

Leading a High Growth Strategy

Since it was founded sixteen years ago, the Hilb Group—a successful middle market insurance broker—has embraced a high growth strategy. And in just over a decade and a half, the organization has acquired almost two hundred small agencies and brokers across the country. While focused on the growth, Hilb's leaders also work to maintain the health of the organization, customer satisfaction, and financial discipline. Jason Angus is the Hilb Group's Chief Operating Officer. He joins us today to discuss the insurance sector, leading a fast growing organization, and the elements of effective leadership; including communication, patience, and passion.

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Show Notes and Transcript

Show Notes

  • What the opportunities and challenges are now in the insurance industry
  • How Jason's career trajectory led him to insurance
  • How the onset of AI is affecting the insurance industry
  • What the biggest industry change has been in the past 10 years
  • What it's like leading an organization under constant change
  • How important passion is for the role of the leader
  • What qualities make a good leader

Transcript


Jason Angus

You've got to love the business. You've got to want to love it, not from what can we accomplish and how can we get to this next growth level, but also the difference that we can make in people's lives. What's that real charge to get to work and see that your helping these associates and giving them tools to have a better life and better job. And the same thing with our clients.

Female Voice

From William & Mary in Williamsburg, Virginia. This is Leadership & Business, produced by the William & Mary School of Business and its MBA program. Offered in four formats: the full-time, the part-time, the online, and executive MBA. For more information, visit wm.edu.

Ken White

Welcome to Leadership & Business, the podcast that brings you the latest and best thinking from today's business leaders from across the world. Sharing strategies, information, and insight that help you become a more effective leader, communicator, and professional. I'm your host, Ken White. Thanks for listening. Since it was founded 16 years ago, the Hilb Group, a successful middle-market insurance broker, has embraced a high-growth strategy. And just over a decade and a half, the organization has acquired almost 200 small agencies and brokers across the country. While focused on the growth, Hilb's leaders also work to maintain the health of the organization, customer satisfaction, and financial discipline. Jason Angus is the Hilb Group's Chief Operating Officer. He joins us on the podcast today to discuss the insurance sector, leading a fast-growing organization, and the elements of effective leadership, including communication, patience, and passion. Here's our conversation with Jason Angus.

Ken White

Jason, thanks so very much for joining us on the podcast. Great to have you here.

Jason Angus

Yeah, thanks, Ken. I appreciate it.

Ken White

You're here quite often, but you are a graduate of the Executive MBA program.

Jason Angus

Let's not attack our admissions team. I'm excited to come back and give back a little bit. As you know, we've been collaborating with William & Mary for some time. We had a big need to build a leadership program and wanted to have basically a mini MBA is what we were looking for. It was not that we were trying to take away from a graduate-level experience, but give people that are ambitious, that are our next generation of leaders, give them a taste for all the different modules that you would find in a more typical MBA program, but people aren't ready for it. We've been just absolutely thrilled with William & Mary, and this is about our fifth or sixth year now with you guys.

Ken White

That's great. We love the partnership for sure. Let's talk insurance, the state of the insurance. When you think that, what are some of the opportunities and challenges you're seeing right now?

Jason Angus

The insurance industry is one of the largest industries in the world. People forget globally. It's involved in just about everything. It's an approximately just shy of $3 trillion industry, which is bigger than most countries GDP. The insurance distribution space falls into a couple of areas. You've got the retail and the broker side, which is where our company sits. You've got the insurance carriers, which are the risk-bearing carriers. Then you have the reinsurers, the global reinsurers, which can participate both as a carrier, but also an insurer of insurance companies. From that perspective, we look at excess policy surplus and their ability to pay claims. That's what carriers are rated. Generally, the industry is barely solved. The combined ratio, which is their claims paid and expenses ratio over the premium dollar, is running about 98% in US right now. That means they're roughly making two cents on every dollar for every insurance premium. As you know, most of that revenue also comes from the investment side of those large insurance premiums. Pretty stable right now. The industry would like to see it come down even further. But what's been driving it of late has been catastrophic claims. We've had some supply chain disruptions over the last five years. 2025 is no different as we're trying to understand companies that are buying parts across the sea, how that's going to be affected by tariffs. That goes into some of the cost modeling that's going to happen when a claim happens and how they're going to be able to pay it back.

Ken White

What do you like about this industry? What attracted you?

Jason Angus

You could probably interview 98% of the industry, and 98% of them didn't plan on being in it. There are a good proportion of people, many of my colleagues who grew up in this space and grandfathers of their fathers. I was a disgruntled consultant. Every year, I was tired of trying to go find the next consulting project. Happened to be working with a lot of great Fortune 500 insurance companies and got introduced to the retail side. I actually got really turned on in the business, and it's surprisingly more creative than people think. In the US, we have a very sophisticated insurance market. It's regulated by each individual's state. Our products are very well-defined, they're very well-regulated in most situations, and we tend to homogenize it almost a little too much. If you go globally, if you ever have the chance to work in London, at Lloyds of London, it is one of the creative, collaborative environments because there's a risk. If you're building a factory in Africa, there's not African insurance companies you're going to. You got to go to Lloyds of London and how they're breaking it up. So they're really understanding the true risk of the business. They got to really understand how that business makes money. And then how do they finance it? Are we transferring the risk over? Are they absorbing it? And those different mechanisms. To me, I think that's probably the weaknesses in industry, and how we bring in that next generation is that we don't spend enough time talking about the creative side of risk management and risk finance. We talk it more about as an insurance product or policy.

Ken White

What about AI, machine learning, adopting that?

Jason Angus

It's like the million-dollar acronym of the day. We as a company are really leaning into it. I would think in most industries, you got a third that are going, okay, I don't want to deal with that right now. You got a third that are trying to understand it. I think it's still somewhat ambiguous in how people are throwing AI on just about everything, whether it really is truly AI or not. Then there's companies like ours that are really excited about it, the idea to automate the mundane. We're focused on what AI can help us and really taking that part of the job where we're moving information from the left screen to the right screen. It's not high-brow thinking, but it's really pulling it off the application and putting into another application. When we can use AI and these machine learning models that can do that for us, it just frees up our people. It makes it that much easier to train and to develop. But right now, we're just asking them to do so much work and so much data that creates a real labor issue for us as a company. We are kind of forward-thinking into it. We've spent the last couple of years trying to teach ourselves from an executive standpoint. We've got an AI task force that's focused on it and how we evaluate products both off the shelf as well as generating some of them on our own. I really think it is one of those areas of the future. Before you can get into it, you got to spend some time relearning what it all means.

Ken White

What's the biggest change in the past, say, 10 years in the industry?

Jason Angus

We've had the same challenges that most industries have. I mean, this last five years, although we'd all prefer not to talk about the pandemic again. Kind of threw a lot of industries up. You saw major workforces go remote. You saw a crazy labor market where people were suddenly able now to work for anybody, anywhere. Remote working became very easy. You've got very tech enablement. You're trying to build those cultures. That was a challenge I don't think is unique to the insurance business or to our company. Really, we all faced together. At the same time, we're getting into these new technologies like AI that are really, I think, going to accelerate the differentiation between those early adopters or not, and so how people were thinking about it. Then, in our world, the insurance business, we really went through about a decade, if you think about 2010 up to about 2017. We had low catastrophic events, created excess capacity. Money was cheap, your cost of capital was lower. Now you've got cost of capital is up, 500 bits. It's still difficult to predict. We've been through some catastrophes, whether wildfires in California to major storms that are hitting. That's a perfect storm of events that make it a little more challenging for them.

Ken White

Let's talk about Hilb. Tell us about the organization.

Jason Angus

Sure. The Hilb Group started in 2009 based out of Richmond, Virginia. We are a middle-market insurance broker, so we're about 65% property and cash and 35% employee benefits. We are very acquisitive in nature. We're private equity-back, so we have had a high growth strategy focused on acquiring like businesses. We bought 195, or what we like to say is we recruited 195 small agencies and brokers to join us and come together. We've gotten some great, fantastic people. We sit today a little over 750 million in revenue. We've got just about 2,600 employees across the country. We're trying to get to that next level for us. The last five years are really focused on integrating those operations and putting in that common tech stack and really building a lot of these applications that have been focused on our associate. We didn't want to get too caught up in the client experience initially. We wanted to make our associate experience that much better. We've been building a lot of the applications, a lot of the workflows, and support to free them up, and the thinking that the more freed up they are, the higher job satisfaction relates to a better client experience.

Ken White

Your role?

Jason Angus

I'm the Chief Operating Officer of the Hilb Group. Currently, I've got our senior management team reports up to me outside of finance and legal and M&A. Basically, the rest of the business falls up to me.

Ken White

We'll continue our discussion with Jason Angus in just a minute. Our podcast is brought to you by the William & Mary Mary's School of Business. When it comes to choosing an MBA program, people sometimes look to the rankings, among other things, for guidance. Well, the William & Mary MBA program is ranked among the best in the world. The Financial Times includes William & Mary's full-time MBA program in its global top 100. Fortune ranks the executive MBA in its top 20, and US News & World Report lists the online MBA program in its top 20. If you're thinking about pursuing an MBA, check out all the indicators of quality, like a world-class faculty, unparalleled student support, and a brand that's highly respected, the William & Mary MBA. Reach out to our admissions team to learn which of our four MBA programs best fits you: the full-time, the part-time, the online, and the executive MBA. Check out the MBA program at William & Mary at wm.edu. Now back to our conversation with Jason Angus, Chief Operating Officer at the Hilb Group.

Ken White

What's it like leading in an organization where you're changing constantly? Like you just said, almost 200 new businesses that you've acquired. What's it like with all that change?

Jason Angus

The change management, it's probably been the biggest challenge for an organization like us. I think anytime you're in any high-growth company, communication is your Achilles heel. You just can't overcommunicate it, right? Especially if you're high-growing and you've got people that are spread all over the country. It's hard to get them in the same room. It's hard get them to feel. You talk about culture, building core values. Well, you bought 195 businesses that were operating 195 different ways and, effectively, 195 different cultures. How do you create that commonality about, no, this is how we're going to do this coming together? It really comes down into just you can't overcommunicate. We've used every Tom, Dick, and Harry method that known to man. We've got a great marketing communications team that's really been forefront in getting that internal brand awareness and understanding what our values are and our culture. It's just consistency of message. I think as executives, we tend to fall into the trap because we think about it all the time, and we may send a email out or put some big posting up, that that's an effective communication. You forget that the average employee's got 365 days of work, and they're focused on it day in and day out. So, yes, they may have read or scanned your message quickly. I'm not foolish enough that everybody savers everything that I say, but in a week, they'll have forgotten it. So, how do we reinforce that messaging and communication over and over? It's been our biggest challenge, but we got a great team that's been really head-on trying to get it. I think every year, we do a little bit better job with it.

Ken White

Then from the new employee standpoint, they were working for a certain agency, and now they're working under the Hilb umbrella, so a lot of changes for them.

Jason Angus

Well, 100%, I think 195 businesses, and just divide it by that size of the revenue. So the average agency was fairly small, so 3-7 million in revenue. So this is commission revenue what they would make as a broker selling an insurance policy. A lot of them, they were small businesses. They didn't have an HR department. They didn't have these kind of professional development. They were thrown in the deep end of the pool and taught how to swim. The good news is very independent, can handle a lot of different things. The downside is they're suddenly now a part of a larger organization, and so they can sometimes feel lost. How do I feel like I fit in? When they were a smaller business, they had an issue. They walked down and talked to the owner, and we got to fix this. The owner listened to them, and they did that. Now they're like, well, who do I connect and how does this work? We never want to really lose sight of that. We never want to be caught up just too much reading our own headlines or reading the spreadsheet, but really try to bring ourselves back to awareness that these are the type of companies that we've acquired have been a part of our organization.

Ken White

I've had conversations with you about insurance, and you get all geeked out. I mean, you really love it.

Jason Angus

That's a nice way to say it.

Ken White

My point is, and my question is, how important is role of passion in leadership? How much do you have to love what you do to be successful?

Jason Angus

In a leadership standpoint, I think it's actually job number one. You've got to love the business, and you've got to want to love it, not from just what can we accomplish and how can we get to this next growth level, but also the difference that we can make in people's lives. What's that real charge to get up to work and see that your help of these associates and giving them tools to have a better life and better job? The same thing with clients. So that's what gets you excited about it. If you deliver that message, and I'll give you an example, we used to say, our goal is to we're going to build a billion-dollar company. It's very easy to say that because you write that down, you can measure yourself to it. It seems very simple. But what we realized is one of our associates, one of our colleagues in an office somewhere, couldn't relate to that goal. It was meaningless to them. They're dealing with $500 to $1,500 policies. They're in a small office somewhere, and it just created a bigger separation between us, corporately to the people in the field. Then we changed that mantra. The vocabulary that we use is very deliberate so that our average associate can talk about what it means to be part of the Hilb Group and what we're here to do.

Ken White

So obviously, communication, you see that as an important quality of a leader. What are the other qualities that make a good leader?

Jason Angus

Patience helps to remember that sometimes we joke that sometimes a strategy takes about five minutes. We know what we need to accomplish, but it's not the strategy, right? It's the logistics, it's how to execute, it's that tactical execution. You got to remember that there are people want to do what's right for the client; they want to do what's right for the company, but they have a just pile of work on their desk. So, any great idea that we can come up with is a disruption. It actually hurts their own productivity. Another way to say is it's making the average associate's job a little worse in a short period of time. Now, Senior executives, we're supposed to be big boys, big girls. We got to think beyond this. We got to think, okay, we know where we got to take the organization. But you got to be careful. You got to be patient enough not to lose that sight of how does this affect our associates in their day-to-day living. So that's another quality, I think, that I probably didn't have 10 years ago. It was just full of ambition, and here's what we're going to do, and lots of energy, and not realizing that the people that were supposed to be following you whose tongues are hanging out. They're trying to catch their breath. You've got to get them in passion. You got to get them to see it. I think that also means that we use a saying we don't have a monopoly on good ideas. Making sure you have the listening mechanisms that are created so the people that are closest to our clients and closest to working on it. When they can raise their hand and say, this doesn't make any sense. As executives, we need to be able to listen to that. We try to do a lot where those key priorities are driven by the lower people in the organization and that they can identify those challenges and priorities. We, as an executive team, can resource it, support it, make sure it fits in where we're trying to go, and then we can move forward.

Ken White

Was there a time that you recall in your life or career where you said, I want to lead, I want to be a leader?

Jason Angus

I think it was one of those. It's like, who wants to volunteer? You weren't paying attention. Everybody stood back, and you were standing out by yourself. I've been in a variety of different leadership roles throughout my career. Early on, I was in sales and sales development. I was in consulting. I really enjoyed working with senior executives. I was I'm very fortunate that early in my career, I had some phenomenal mentors, just in how they thought about everything from database marketing to really just great senior executives. I was consultant with companies like M&A, America Bank, and Capital One, and America Express back in the day, and just got to be around at an early age and just listen to how they approach problems, how they treated their employees. That set a really good example. I remember my father told me when I was coming out of college, he said, always make sure you have a mentor. You can learn more in two years than they can teach you in 10. That approach to always be learning and trying to find those that you surround yourselves to make you better, I think it's been very helpful.

Ken White

You may have answered my next question, and that is for aspiring leaders, what do you recommend they do?

Jason Angus

Yeah, never stop learning. I was fortunate enough to go to grad school at William & Mary. There's your plug, Ken. But I think one of the big lessons that we undersell through that process is that if you don't know something, go get a book and read it. Listen to a podcast. Keep educating yourself. That helps with that side that you need to be passionate about it. You want to learn. But I think that eternal student, that how can I get better? How can I approach it? We refer to it as the professional mindset. If you think your sports analogy and your great Payton Mannings or Tom Bradies of the world, Monday morning, they still review tapes. They're still learning how to get better. They're still pushing themselves. I think professionally, we should never sit back. There's always going to be a new piece of technology, a new challenge, and you need to embrace it and jump on it and learn and listen.

Ken White

That's our conversation with Jason Angus, and that's it for this episode of Leadership & Business. Our podcast is brought to you by the William & Mary School of Business, home of the MBA program offered in four formats: the full-time, the part-time, the online, and the executive MBA. Check out the William & Mary MBA program at wm.edu. Thanks to our guest, Jason Angus, and thanks to you for joining us. I'm Ken White, wishing you a safe, happy, and productive week ahead.

Female Voice

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