Amy Zupon
CEO of Vertafore
From very early in my career, I have believed in giving people opportunities that they have earned, having high expectations for them, and supporting them along the way. To do those three things, you have to create a culture of openness and you have to create a culture of vulnerability.
Summary
This week on “Leadership Matters,” Alan is joined by Vertafore CEO Amy Zupon. An insurance technology provider, Vertafore serves companies of various sizes and has played a key role in driving modernization in the industry, offering solutions that are created in dialogue with its customers. Since becoming CEO in 2016, Amy has played a transformational role at Vertafore, creating a vibrant company culture that has inspired further innovation and attracted top talent.
In their conversation, Amy and Alan discuss her early life and career, her introduction to the technology industry, and the opportunities that Vertafore has to further empower insurance providers to overcome the challenges of the future. Amy emphasized the importance providing her team opportunities to solve problems creatively. Mentorship, in her experience, is a two-way street; leaders should be ready to coach their teams to tackle unfamiliar challenges, but also to embrace the opportunity to learn from those results.
Mentions & Resources in this Episode
Guest Bio
As CEO of Vertafore, Amy has a strong passion for providing an exceptional experience and products that deliver real value and performance for Vertafore’s customers. Her approach drives Vertafore’s commitment to continuous improvement through a vibrant company culture that inspires employees to innovate and be creative to solve customers’ ever-changing needs.
Amy is a veteran software and data solutions executive, having spent two decades in senior leadership roles in the B2B software industry. After beginning her career as a senior consultant at Deloitte, she spent nearly 10 years as a partner at The Structure Group, an IT services consultancy acquired by Accenture in 2015. At Ventyx, an ABB Enterprise Software company, Amy served as EVP, Global Client Services and SVP and General Manager of enterprise solutions. Prior to joining Vertafore, she spent four years in the C-suite at P2 Energy Solutions, the largest software and technology provider to the upstream oil and gas industry, first as CTO, then COO and finally as CEO.
Amy earned a BA in mathematics from Northwestern University.
Clips from This Episode
On the importance of accomplishments you can point to when building your career
Amy’s experience as a woman executive in the tech and insurance industry
Reflecting on her decision to join Vertafore and the development of the insurance industry
Episode Transcription
Alan Fleischmann
You’re listening to “Leadership Matters” on SiriusXM and leadershipmattersshow.com. I’m your host, Alan Fleischmann.
I’m here today with an amazing leader and entrepreneur who has been an executive and CEO helping companies across industries modernize through new, innovative software and technology. Amy Zupon is CEO of Vertafore, an insurance tech, or insurtech, software provider that serves companies from the largest insurance providers to the small mom-and-pop agencies. Since taking the reins at Vertafore in 2016, Amy quickly transformed the company with a team that she put together and has been working with ever since, helping it to better serve the evolving needs of its many stakeholders. All the while, she has built and maintained a vibrant company culture at Vertafore that has drawn in some of the most impressive talent in the industry. I’m thrilled to have Amy join us today to discuss her career in the software industry, the key elements of her leadership, and the advice that she would give to leaders who are looking to undergo similar, impressive transformations of their own companies.
Of the people I know in the world who least likes to talk about herself, I would put Amy near the top of that list. So I’m especially grateful that she has been willing to come on “Leadership Matters.” It’s a pleasure to have you here today.
Amy Zupon
Thanks, Alan. It’s honestly great to be here, I appreciate it so much. I admire your work and I am honestly humbled to be invited to talk with you today. So thank you.
Alan Fleischmann
It’s my honor. I know that everyone who’s listening is going to feel the same way.
I’d love to have people have a sense of your journey. Let’s start by talking a bit about your family and your upbringing — where did you and your two siblings grow up, what your parents do, and what was life around the house?
Amy Zupon
Yeah, absolutely. So, I grew up in Pittsburgh, Pennsylvania. I live in Denver, Colorado, today, but I’m very proud to be raising two Pittsburgh Steelers fans in my house. You can’t take me out of that city.
I’m the oldest of three, I grew up in a really tight family. They’re all just great people. When I was reflecting on this conversation, I think the greatest gift of my life was being born into a family that was filled with just truly wonderful people. My parents were clearly the most influential role models that I had as a kid and honestly, throughout my life. My dad was a self-made man — It was actually super inspiring Alan, how he grew up with very little, navigated tons of struggles in life, and became an incredibly successful businessman. He was quite the character, you would like him a lot. He brought life and laughter to just about every situation. But he was someone who told it like it is, whether you wanted to hear it or not. Sometimes Alan, I’ll tell you, I did not want to hear it. But in the process, I think he taught us all as kids to be humble, work hard, be strong, believe in yourself, show up in life, laugh, and be great.
Alan Fleischmann
What kind of work did he do?
Amy Zupon
He actually went to school to be an engineer and ended up running a manufacturing company. They manufactured coils. They acquired about 20 businesses and then he ultimately sold that to Siemens, which was kind of his legacy.
Alan Fleischmann
And your mom?
Amy Zupon
My mom, she’s the nicest, strongest woman I know, Alan. I reflect back, and you could back then — and you still can — tell her anything. She was always the one in the family who wanted to talk it out. No matter what was going on, no matter what the issue was, she wanted to talk it out. I hated it at the time but it is a skill that I’m so grateful I now have today, for what it’s worth.
Alan Fleischmann
So it sounds like neither of your parents were the kind of passive-aggressive types; they were great listeners and great at telling you what they felt.
Amy Zupon
They were very good at telling you what they felt, making sure you knew where you were strong, where you had opportunity, when you did something wrong, and praising you when you had great success. They were my biggest cheerleaders and my biggest critics all at once.
Alan Fleischmann
That’s amazing. And your mom still lives in Pittsburgh?
Amy Zupon
My mom actually kind of lives a little bit in Denver where we are, a little bit in Pittsburgh, and mostly in South Carolina where she has a condo on the beach.
Alan Fleischmann
That’s so smart, it sounds like she knows what she’s doing.
And are there other mentors and role models, in addition to your parents, who played a critical role in shaping you as you grew up?
Amy Zupon
I was a soccer player as a kid, so through that I had a whole slew of coaches, teammates, friends, and whatnot. I was the goalie, and I always kind of reflect back to that. Being part of a team — which, you know me, it’s a super important aspect of how I lead to this day — started way back when I was playing soccer. Because we won and we lost together, no matter what happened on that field. Learning to play position and learning to play with one another was super, super important. So some great successes and some great fun times, but I learned a lot in that structure.
Alan Fleischmann
How long did you play soccer?
Amy Zupon
I played through high school, I stopped at college. I was going to play in college and then realized that was not the future of my life, so I better turn and find something new to have to be passionate about.
Alan Fleischmann
I remember you saying that you wanted to be a doctor at one point, you planned on going to medical school? Did that influence your choice to go to Northwestern University? Did you think of pre-med when you were looking at there? I know that you ultimately studied mathematics.
Amy Zupon
You know, I looked for a great school that was well-rounded and going to give me a solid education, and that’s what ultimately led me to Northwestern. I majored in math because I was good at it, quite frankly. I wanted to be a doctor, which is why I went into pre-med.
Alan Fleischmann
That’s cool. And was it hard to decide where you wanted to go to college?
Amy Zupon
No, it was pretty easy. I went in and I met with a guidance counselor. To be honest, I had never heard of Northwestern when I sat down and met with the guidance counselor. I wanted to go to the West Coast, I wanted to go to the sunshine. I sat down with a guidance counselor and they said, “Actually, you should look at this school.” I went to visit Northwestern and fell in love with everything about it. So when I got into Northwestern, it was a super easy decision.
Alan Fleischmann
Would you recommend that that was the right decision, to go mathematics first and then playing from there? It seems like a great foundational focus.
Amy Zupon
Yeah. So technically, my degree is a liberal arts degree. What was really interesting is, it’s a technical focus and it’s very analytical in the skills that you learn. Even today, I lean on a lot of the logic and the breaking down complex problems into simple things. But I got a liberal arts degree as well. So it was a really well-rounded education, that’s the way I would describe it. I never felt pigeonholed into anything when I graduated, I honestly felt like I had a tremendous amount of opportunity.
Alan Fleischmann
Were you already thinking technology was the future? Because I think of you being such an incredible entrepreneur, and CEO when it comes to advancing tech for good. Was technology a part of your future? Or was it mathematics, and technology came later?
Amy Zupon
So here’s the interesting part, I actually chose to take a few years off of school before going to medical school. That’s what happened. I still remember the conversation with my dad when I told him that. The disappointment was real, Alan, in that conversation. But that is when I actually got introduced to technology.
So throughout college, I did not have technology as a lens of where I was going to go with my career. It was actually through my first job out of college, which was at Deloitte Consulting. I served state government building and implementing welfare systems — think food stamps, Medicaid, cash benefits. I majored in math, so I clearly liked the technical aspects of the subject. But I had never been introduced to the tech field until that experience. So to me, making that decision and going to Deloitte was truly pivotal for me. I discovered in those first few years that I loved it and I was good at it, which at the end of the day, is what you’re looking for when you’re thinking about your career. And I never turned back.
Alan Fleischmann
So when did you realize medical school was not going to be the future?
Amy Zupon
Oh, gosh, I probably held on to that idea my first couple of years, thinking I would ultimately go back. And then, when I had an opportunity to join a startup company and I took that opportunity, that’s when it felt like the door closed at going back to medical school and I really had found something that I was super, super passionate about.
But I have to say, I am so appreciative of my time at Deloitte. They threw me in the deep end. I was a kid out of college with no technical experience, they had high expectations for what I could do, and they supported me every step of the way. And I tell you, as I reflect on leadership, those are three things that I very much try to emulate for my teams every day, which is: challenge them, believe in them, expect great things, and then support them in every way that you can. So for a girl who never had worked in technology, I had some pretty great teachers back then.
Alan Fleischmann
Were you traveling a lot during that period at Deloitte?
Amy Zupon
I sure was, yeah. I graduated, I went to work for Deloitte, and I thought they were gonna send me to San Francisco and New York City, all these great places. And they sent me to Charleston, West Virginia, where we were implementing the welfare system for the state of West Virginia. They gave me a shiny blue Corsica, and I drove back and forth from Pittsburgh every week, Monday through Friday.
I have to tell you, I loved it. I loved everything about the small town, I loved getting involved in what the state was doing. I loved kind of the team atmosphere of everybody traveling down together and working hard on these projects and enjoying the weekend. It was a really great couple of years for me coming out of school.
Alan Fleischmann
That was a coal mining capital, wasn’t it? So that must have been a community and transition as well.
How long were you at Deloitte?
Amy Zupon
Only a couple of years.
Alan Fleischmann
And then you went from there to the Structure Group?
Amy Zupon
I sure did. So after those couple of years at Deloitte, through a friend of a friend I had this great opportunity to join a startup company. I was still super early in my career. In all honesty, it was really that experience that solidified kind of my path forward. I ended up spending nine years at this startup company and it was just an amazing experience.
So one of the things that’s been a huge constant in my career is, I’m always attracted to the hard job at every company. This is something you should know about me. I love a challenge, I’m not afraid of hard work, and at this startup it wasn’t any different. The Structure Group, you know, we were primarily a consulting firm at first. We had this opportunity to build a software platform to address some emerging needs in the energy and utility space. At the time, energy was deregulating in North America. I was asked to build a team, lead a team, build some software products, and ultimately build the operations of the business. We had nothing.
It proved to be for me, and probably still is today, one of the most fun times of my career. Throughout this nine years, we built a successful tech company in the energy and utility space. We had an amazing team of people show up for the party, we solve some unique problems in the market that were emerging problems, so they hadn’t been solved before. And we experienced this phenomenal success together. It was crazy hard work: long, long hours, most weekends. My boyfriend at the time, who’s my husband now, would fly in to see me and I’d say, “Hey, we gotta go test at the office.” But this time of life, it was magical. I learned so much in this environment and just had so much fun. It was a really great experience.
Alan Fleischmann
And you were there for nine years, so leaving there must have been hard.
Amy Zupon
Well, so what happened was, we actually sold the business to a private equity company. When we sold the business, I got introduced to the world of private equity-backed software companies. That is how I made the transition from that startup environment to private equity-backed software companies and taking various leadership roles throughout all of that.
Alan Fleischmann
Were there certain skills you can identify that came out of those nine years at the Structure Group that would be attractive to the investors and partners that you were about to meet? And did they also see that you had experiences, where you took on the very difficult assignments along the way, that would be valuable to them?
Amy Zupon
That’s a great question. I would tell you that, probably first and foremost, when you’re trying to grow your career, people are looking for accomplishment. So I tell people all the time, do the work. There’s no substitute for doing the work. If you want to find the next opportunity, you need to achieve, you need to demonstrate accomplishment. I think one of the things that the firms I had the opportunity to work with valued in me was, I was not afraid to do the work, work hard and drive accomplishment.
At the same time, I think the startup experience that I went through, which I’m incredibly grateful for, is where I truly learned the power of a team and how to lead a business with a mission, a spirit, and a culture that is infectious, with a work ethic that is almost inspiring. As a result, we achieve more than I thought any of us could do individually, we achieved it together as a team. I think, again, back to that sense of accomplishment; that sense of digging deep and doing the work was something that people saw in me.
Alan Fleischmann
That’s great. I love what you’re saying here, that nothing was beneath you. You were willing to roll up your sleeves and jump in even the most difficult tasks.
That’s a great thing for people to remember. Because often, people think to themselves, “Well, I can’t do that,” or “I don’t have any experience doing that.” They don’t realize that the people that succeed are the ones who may not have any more experience than you do, but they’re gonna raise their hand to say, “I’ll take it on,” knowing that they’re going to learn on the job. The more senior people will applaud people who raise their hand, who say, “I’m in it.” That becomes a part of your reputation and then, obviously, that drives the opportunities.
Amy Zupon
Yeah. It’s interesting, one particular mistake I see a lot of people make is thinking I should know it all. I should know how to do everything in my role. I actually find that people who know what they know, know what they don’t know, and are willing to do the work to figure out the rest — those are the folks that you see drive success at the fastest pace. They get the most opportunities because, as leaders, you say, “Look, I understand they know what they know, they know what they don’t know, and they’re gonna work hard to do the rest. That I can coach.”
Alan Fleischmann
There’s this great adage in the world, and it’s true: if you want to get something done, go to the busiest person you know. They’re gonna know how to get that something done. The other thing is to go to the person who’s going to ask the right questions. You’re more likely to ask the right questions if you don’t think you know everything about what you’re about to take on, because you want to get it right. Versus someone who says, “Oh yeah, I know it, I’ve got a lot of experience, I understand this problem.” And they don’t ask any questions.
Knowing you as I do, you’re going to encourage people to ask questions, but you’re also going to ask them to make sure we’ve got our ducks in order. Let’s make sure we’re all speaking from the same script. That’s important.
What were the different iterations of jobs you took on after the Structure Group was sold?
Amy Zupon
So, the Structure Group was sold to a company called Ventex and I became a lead product management leader. So I went in to the product management arena, initially. In product management, you know, you cross departmentally, or in a dotted-line fashion, to lead a particular product line — the development, the support, the service, et cetera. I continued to have the products that we supported at the Structure Group, plus incremental projects.
I would say, over the course of the next 18 months, my role at Ventex grew, and grew until I ultimately became the COO there. I ran Professional Services at Ventex, for a global organization that was about... We probably had 2,000 people across the globe. So I got tremendous global experience by joining this larger company. That helped me grow up a little bit, if you will, as far as thinking about how to take a lot of the skills that had made me successful to date and try to apply them at scale, in much broader and larger organizations.
Alan Fleischmann
Talk about culture a little bit, because I imagine looking back, each one of these experiences you’ve had — Deloitte, the Structure Group, and these early businesses that you kind of grew in — culture had to be an issue too, because they all probably were very different.
Amy Zupon
They were, but they were filled with similar things that that I’m attracted to. Which is, I like organizations that are rooted in strong values — that do the right thing, make customers successful. If you look at the roles that I played and the companies that I was a part of, those are the core beliefs I always felt super strongly about holding true to. I could not stay in an organization if I couldn’t find those particular things.
Alan Fleischmann
Did you have choices early on to pick which companies you would work with? Were you volunteering and saying, “I want to work there,” when you started to work with private equity after the Structure Group?
Amy Zupon
So, when we sold our business it was actually folded into Ventex, so I was inside of Ventex. I was there for a little while, all the way through to when the private equity firm sold Ventex to ABB. Then is when I started to have opportunities to go back and work with the private equity firms and have conversations about which companies that might be a good fit for the skills I brought to the table.
Alan Fleischmann
That’s great. Any mentors in that journey that you want to highlight too, people that actually stepped up? At that point, you were also becoming a mentor to other people as well.
Amy Zupon
Well, I think one of the things you learn early on is that you’re always a mentor to others and you always look for mentors. It’s a full circle. In all honesty, a lot of the people that I mentor mentor me at the same time, and vice versa.
There’s so many people to look back and say, “Gosh, this was such a tremendous opportunity.” There was a gentleman at Ventex, Steve Carpenter, who I developed a terrific relationship with and we worked really well together. He was one of the people that was constantly pulling me into something new, “Amy, hey, we need some help over here. Can you help?” “Yes, you got it.” Charles Goodman was the CEO of P2 Energy Solutions when I got the opportunity to go over there and be the CTO. He was another person in my career journey who would say, “You know what, Amy, the head of Marketing just left. I know you’re the CTO. Can you run marketing for a while?” Sure. “Hey, Amy, our sales operations leader left and we need to do sales compensation plans. Can you take that?” Sure.
I look back at all of those moments where somebody reached out and said they needed help — I say those were probably the best opportunities of my career. Because in each one of those things, I took on something I didn’t know. I learned, I asked a whole bunch of questions, and I had the opportunity to do the next thing. I think if you asked those folks, they would tell you, Amy was someone that I could lean on in those moments to really help me. So as much as they were helping me, I was helping them, which is kind of what business relationships are about.
Alan Fleischmann
And were there people that you started to work with that were working with you for years?
Amy Zupon
Oh, yeah. I was just telling the story the other day. Liz Nguyen is the chief technology officer of Vertafore. She works with me today, but she and I started working together at the Structure Group when I first joined back in 2000. So we have worked together for more than 20 years today, which is just crazy. As I interview new folks, I say, “Anything you want to know about me, you can ask Liz, because she’ll tell you the good, the bad, and the in-between.”
Alan Fleischmann
That’s awesome. That also creates a culture of trust as well, because you’re working with people that know you, you know them. They know to expect a lot from you and you know to expect a lot from them.
I’m really big on the culture part with you, because I know that what you said early matters so much to you, this idea that we are a team. It’s all about structuring and creating a culture of teamwork. It’s a big part of who you are. Obviously, that got established along your journey, but it’s certainly a big part of your CEO-ship.
Amy Zupon
100%. I mean, you know me. I’ll tell you a story here — When I first joined Vertafore, obviously, defining our strategy, setting our charter, and knowing what success looks like were super important things to do, to knock down and make sure everybody’s aligned. It was also really important for me — for us as a team, quite frankly — to define who we are, how we want to interact with each other, with our customers with the industry, and what mission we’re going after.
If you think about my history, I saw firsthand in that startup the power of a strong culture and a mission-driven team. I wanted to bring that out at Vertafore.
Alan Fleischmann
Did that come when you were at P2 Energy Solutions when you were CTO, or is that something where all the different experiences kind of laid out the kind of the blueprint for Vertafore?
Amy Zupon
So, all of the experiences. I actually first created the P2 Way when I was at P2. Then when I went to Vertafore, I kind of approached it slightly differently, but with similar intention: to essentially unite a team of 2,200 folks behind a core mission and a core culture that would be something that the team was excited to be a part of. That gave you that exponential lift, if you will, to really drive business results. I firmly believe that having a strong culture is foundational to having a successful business.
Alan Fleischmann
That’s very cool. Tell us a little bit about that experience you had before Vertafore and your roles there.
Amy Zupon
Back at P2 Energy Solutions? So at P2 Energy Solutions, I was the Chief Technology Officer, which meant I ran the product management group and I ran the building of all of our products; the development organization. Over time, I picked up more and more responsibilities. I was mentioning Charles earlier — he would say things, we would lose people, somebody would move on, we’d have a big initiative, and he would ask me to step in and lead.
Throughout that whole time period, every time he asked me to take on something new, I was always the chief technology officer. My title didn’t change throughout that time, but my experience changed significantly. I learned how to run sales, I learned how to run sales operations, I learned how to run hosting organizations and support organizations. When Charles eventually retired from P2 Energy Solutions, at that point I was the natural selection to be asked to become the CEO. That was my first time as CEO at a private equity-backed company, at P2 Energy Solutions.
Had I not taken advantage of all those opportunities along the way to learn… It is not common for a CTO to become the CEO in private equity-backed companies. People often ask me how that happened. And honestly, it happened just because I was willing to take on a lot of different things that they needed in the business and I learned a ton along the way.
Alan Fleischmann
And how long were you there?
Amy Zupon
I was at P2 almost six years.
Alan Fleischmann
And was that the job just before you went on to become CEO of Vertafore?
Amy Zupon
It sure was, yeah. I went from P2 Energy Solutions and then I became CEO of Vertafore. And I’ve been at Vertafore now about six years.
Alan Fleischmann
Tell us about that decision to go to Vertafore, because it’s really exciting.
Amy Zupon
Yeah. You know, it’s funny, I was very happy at P2. It was a terrific company, it was backed by a terrific group of private equity partners; I was not looking to go do something new. But what I found in Vertafore was this company that had been around for 50 years, it had an enviable list of customers in the insurance space, and it was in an industry — in insurance — which was, frankly, super thirsty for technology advancement to help drive some real value and change for their businesses. Vertafore was a business that had grown through acquisition and had done a decent job of integrating over time. But at the same time, Vertafore was a company that, operationally, could be so much better. We could do so much more and deliver so much value.
Throughout my career, I’ve always been a product person. I loved my startup experience. And what I found with Vertafore was an opportunity to reinvent a company, tugging on my startup experience, while investing in technology, tugging on my product management love, to really drive value for our customers and our stakeholders. But to do all of this at scale. Not at a startup where you’ve got a blank sheet of paper, but to do this at scale. That, to me, was a super exciting opportunity. That’s what made me make the change.
Alan Fleischmann
And you saw the industry changing a great deal as well, I imagine.
Amy Zupon
We sure did. Like I said, insurance is behind the times on driving advancement in many of the areas that we work in the distribution channel. The sheer act of buying an insurance policy, at times, can cause people to enter the same data six and seven times in different systems across the board. There’s no reason for that in today’s technology world. We can solve those challenges.
At the same time, the end customer has much higher digital expectations. They want to have the opportunity to interact with customers, interact with you in an omni-channel way, however they want to do it. Whether they want to call you, whether they want to do it on the website, whether they want to do it on the phone, whether they want to email you. I think having insurance truly step up to the table with some of this digital evolution makes this a super exciting time.
Alan Fleischmann
It’s a time, actually, where there’s so much risk, but there’s so much reward if you have the right insurance. I mean, you can’t have entrepreneurship without risk. You can’t have, you can’t deal with some of our biggest challenges in the world right now without risk. Whether it’s cyber issues, or culture issues, or climate change issues, there’s a lot going on in the world right now that all require a thriving insurance industry.
Amy Zupon
I say this often, but my analogy is, if you think of the insurance agent of yesterday, they were more of a transaction processor. You call them, they got you a policy, and you were done. The insurance agent of today and tomorrow is really more of a risk advisor. They’re there to help you as a business understand what kind of cyber insurance you really need. It’s a complicated topic for a business to think through. That’s what they’re there to do.
What we’re here to do at Vertafore is to enable that by automating and simplifying all of the processes that have to happen, to give them the time back to be effective risk advisors. That’s what we’re really trying to do here at Vertafore, it’s what we’re 100% about.
Alan Fleischmann
At all levels of scale, right? It’s the entrepreneur with one or two people all the way to the largest of the largest companies in the world.
Amy Zupon
That’s right. We service agencies that have maybe one or two employees all the way to your largest insurance agencies and insurance carriers, household names that you see on TV with all their commercials and slogans and whatnot.
Alan Fleischmann
How do you build a culture, then, at Vertafore, that understands that? I know you know that every client matters, every customer matters. How do you build a culture where they take everybody to a level of high importance, from the customer that is a one- or two-person mom-and-pop shop — which is so important, which families depend on — to the big insurance companies that are iconic brand names?
Amy Zupon
So I might break that question down into two pieces, First is getting anchored around a culture that believes wholeheartedly that, if we make our customers successful, we will be successful as a company. So when I first joined Vertafore, we ran a grassroots effort. It was built through conversation and discussions across the business, very intentional exercise. But the idea was for us, a team of 2,200 strong, to unite around core principles of our culture that we call the Vertafore Way. What I will tell you is the customer-first culture was always there in the people of Vertafore. But I really used this grassroots effort to bring it out and to give it strength, to give it a belief that not only do you, an individual, believe that, but we, as the strong team of 2,200, believe that.
The second thing is, you have to feed it. You have to establish process and practice that can actually empower your teams to deliver on it. That’s everything from using it in our company rewards programs, to performance conversations, to interview questions, to making sure that the data that our teams need to service their customers is readily available to them. I think how we keep it going is, we lead from the front. We demonstrate it every day. Whether it’s managers in the team, whether it’s leaders, whether it’s my executive teams, I think really demonstrating it is the key to making sure that it continues to have the life that you that you need it to have.
Alan Fleischmann
Then along the way, you’ve made some pretty amazing acquisitions as well. Do you see those as reinforcement moments, to strengthen the culture that you’ve been building with your team?
Amy Zupon
100%. We continue to be an acquisitive company. We made two highly effective acquisitions in the last 10 months, both brought in for the same reason: great products that are serving unique things in the industry and incredibly talented people that share that passion for making customers successful. When you look at companies, one of the components that we’re always evaluating is that cultural fit. Each company comes to you with their own personality.
From that very first moment when you’re meeting with them, you’re trying to assess: How are these individuals and that company going to thrive inside of our business? What are they doing that’s just super awesome and unique and fun that we should be adopting? If you believe that there’s this nice, strong fit, the key is being very intentional about effectuating that melding of cultures. I use the word melding: it doesn’t matter if it’s a large acquisition or a small acquisition, it’s a two-way street of respect, listening, and opening dialogues. That’s really what helps build trust and build those cultural moments. But you gotta be intentional about it, it doesn’t just happen.
Alan Fleischmann
And how do you do it in the age of Zoom, when people are living in different towns or cities? Do you find that it made it an easier thing to do, when you made those two major acquisitions in the last 10 months of AgencyZoom and MGA Systems? Are you all in different locations? And then, you’ve got your own people that are not all in Denver as well. How do you do that over Zoom? I’m curious, because I imagine it can be very effective.
Amy Zupon
I would say, there’s good parts and bad parts to it. On the positive side of being over Zoom, you get to know people in ways that you wouldn’t get to know them at the office. You get to meet their dogs, you see the kids running around, you get to know people in a really great way. I think that applies both to people within my organization, as well as meeting folks through acquisitions. I will tell you, I think these last couple of years, while really challenging, have really taught us all to be empathetic leaders as you work through things. Because everybody’s going through something and everyone’s having a different perspective. I think these last couple of years have really, really taught us all that.
At the same time, there is no substitute for having opportunities for team building, being together, and working through and problem solving. So for me right now, it’s about striking that right balance, Alan.
Alan Fleischmann
Are these catalytic moments when you bring in others? You obviously came into Vertafore and you’ve been transformational with your team, changing its culture, scaling it, and innovating. That’s all cultural transformation, you’ve been doing that. And then these moments when you bring in other firms who are now part of the family, they’re kind of catalytic moments where you can actually take things further.
Amy Zupon
It’s a great point.
Alan Fleischmann
So tell us a little bit about that part too, because I imagine these are accelerator moments for you.
Amy Zupon
Yeah. It’s moments because you have the opportunity to do something, launch an initiative with a lot of intention and transformational intention. I like to describe it like this: there’s continuous improvement, which is where we get better every day, which we all try to do. Then there’s real transformational change. And transformational change requires a start, an expected finish, a project plan, resourcing dollars, et cetera. When we do these acquisitions, it gives us other transformational moments to lead. Transformational moments create opportunity for people to step up, which also continues to build culture, because people are looking for those challenges and those opportunities. Setting it up to make sure that you’re celebrating that and enabling that success is really, fundamentally important.
At the same time, we’re acquiring companies that are much smaller than we are. They have great cultures, they have core cultures, and they know what it’s like to run in small organizations. Bringing some of that entrepreneurship and that excitement into our organization on a regular basis is actually really powerful.
Alan Fleischmann
So it becomes catalytic the other way around as well, which is great.
Being in the line of work that you are, and having the customers that are in the line of work that they are, I imagine that, with all the challenges in climate change and energy, some of the risks in our world, there’s enormous opportunity for them to lead and to become more effective and more efficient. As you put customers first — and I know that’s what you do at Vertafore — how do you actually, from the independent insurance agent to the big companies, develop products that can transform their ability to seek these opportunities and seize them? How does the supply and demand work?
Amy Zupon
I think it’s a great question. When I came to Vertafore six years ago, we were largely an acquirer of businesses. That’s where we got a tremendous amount of our innovation from. Don’t get me wrong, we continue to do that and we will continue to do that. At the same time, a lot of the challenges and opportunities to solve that are really going to drive real value, those things don’t necessarily exist today. So we needed to go on our own journey of transforming our ability to build inside of our organization that has traditionally had its innovation fueled through acquisition. We have been on that journey and are 100% both evolving existing products and building new product to tackle challenges that we see in the industry that we have validated with our existing customers.
The benefit of being 100% focused on insurance is, we have very tight relationships with our customers. We validate consistently, all the time, with leaders, with users all the way through the chain. With the small guys, with the big guys, in separation. Where are the biggest areas of opportunity and pain that they’re feeling? And how can we build to solve it?
Alan Fleischmann
So the customer actually gets notified, if you will. Informed that we’re taking you here because that’s where you need to go, that’s where you say you want to go, and that’s where we’re going to help you get to.
Amy Zupon
100%. What’s fun about that is, here’s where we’re going, here’s why, and tell me if we’re wrong. To really be able to engage senior leaders in conversation is a powerful thing. You become more of a thought partner with your customer than a service provider, which is what we aim to be. We want to be a thought partner, not just a service provider.
Alan Fleischmann
You’re listening to “Leadership Matters” on SiriusXM and at leadershipmattersshow.com. I’m your host, Alan Fleischmann, and I’m here today with Amy Zupon, CEO of Vertafore, and we’re discussing her career, her company, her team, and some of the innovations that they are creating — not only through acquisition, but through the ingenuity of their product offerings to help their customers help us, as we are dealing with great risks, but also a great opportunity, through insurance. So it’s an exciting time, in many ways, because it does unleash the entrepreneur in each one of us.
I’m curious: you’re a CEO in a company that is a tech company in a tech industry, and you’re also CEO in the insurance world. Both are pretty male-dominated. Thinking about it historically, it’s unique when you look at the Vertafore leadership team to see how many women there are. With so much talk about diversity and inclusion, DEI, can you talk a little bit about how you provide pathways for success, especially for women and minorities?
Amy Zupon
Thank you for saying that and asking that question. I think one of the things I’m very proud of is how many women we have inside of Vertafore, doing wonderful and amazing things. I’m also very proud of women that have come through Vertafore and have taken their next opportunities to even step up and do the next great thing.
I will tell you, when I went and started looking for our leadership team when I came on board, I did not set a target. I did not say, “This is what I’m looking for. I want this type of ratio.” That was not my objective. I just went out to look to hire the best people for the role. Upon reflection, when I look back, I think one of the things that has fundamentally been proven out is the power of role models in organizations. I’m obviously a female CEO, and I think people who can look and say, “Hey, she can do it. I can do it. She can do it. I can take this.” I think that we’ve seen that play out at Vertafore. So, as we think about things that we can do for diversity and inclusion, it’s very front and center for us and something that we’ve been very intentional at responding to right now. I think about the aspects of role models: where we have role models, where we don’t have role models, and how that helps inspire others to know they can do this.
Alan Fleischmann
Do you have a certain leadership style? And is part of that leadership style built on mentoring others or creating a culture of mentoring others?
Amy Zupon
I 100% believe… I mean, I said it earlier. From very early in my career, I have believed in giving people opportunities that they have earned, having high expectations for them, and supporting them along the way. To do those three things, you have to create a culture of openness and you have to create a culture of vulnerability. Because by nature, you’re going to be pushing people beyond things that they’ve done previously. You want people to say, “I need help. I’m looking at this, I see this problem, let’s work through that together.” I think my leadership style is that way, and I think the benefit of that is it creates a much more open and vulnerable environment to have conversations that maybe you might not have otherwise.
Alan Fleischmann
That’s great. And do you have town hall meetings, all-hands meetings, things like that, where you have conversations and to bring outside people in?
Amy Zupon
So we have internal, quarterly all-hands, that has an Ask Anything section at the end. I will tell you, my team asks anything. It’s question, question, question, and we answer those questions as they come in as directly and transparently as possible.
We also launched, in mid-2020, a series called Voices for Change at Vertafore, where we have invited diverse leaders in to have a fireside chat with me, to share their own stories, and engage in discussions about how we as individuals, and as a company, can work towards a more just and equitable society. I have to tell you Alan, you were a big part in partnering with me and creating this. I thank you for that, because it has been truly impactful in our organization.
I made the mistake in the very first conversation of saying, “I want to make these conversations comfortable.” I was quickly taught that it’s not about making them comfortable; it’s about getting us comfortable having uncomfortable conversations. It was very powerful statement to me, and our Voices for Change initiative demonstrates to the organization and facilitates these uncomfortable conversations, which has been helpful to us on our journey. Because it is a journey that we’re all on together here, not a not a destination.
Alan Fleischmann
In some cases too, you want to repeat the conversations to make them become part of that culture and ingrained in our greater communities and society.
Are there conversations you think we need to be having more and more now in the work environment to move the needle?
Amy Zupon
Yeah, absolutely. It kind of spans all levels. I mean, there’s conversations about recruiting, sourcing, tactics, interview structures, or things of that nature. Those are tactical conversations. But there’s also conversations… I joined recently a group called the Colorado Inclusive Economy. It is a nonprofit here in Colorado. It is a group of CEOs, and their diversity and inclusion leaders, that are working together in cohorts for a more inclusive economy in Colorado. So some of these appreciations and realizations that, yes, as business leaders, we can do things in our own organizations. But how do we actually facilitate that conversation across? I’m honored to be part of this Colorado Inclusive Economy. The team has just facilitated tremendous insights and knowledge these last six months as I’ve been part of that.
Alan Fleischmann
I love what you said a minute ago about the uncomfortable, that we should be comfortable having the uncomfortable conversations. Because it’s true, we can’t create a dialogue or language that we can all adopt which is built on respect unless we actually can talk about the things that that could potentially divide us. You can’t build bridges without first figuring out what is it that connects us and what doesn’t connect us.
Amy Zupon
That’s right. And how to create safe spaces to be vulnerable in moments, have mistakes, and have that dialogue. I think that’s what involves all of us. I think that’s what Colorado inclusive economy is trying to do. I think that’s what we’re trying to do with Voices for Change for our organization.
Alan Fleischmann
Have you discovered ways to do that, that you have tested to kind of prove that these are the best ways to approach conversations? Is it better have large ones, small ones, or combinations of both?
Amy Zupon
We do a combination of both. So, the Voices for Change initiative is the whole company. It’s a similar concept, it’s over Zoom and you can ask anything. So put in your questions and I ask them in the discussion. So, large group.
Not everybody’s comfortable with that. So we also have what we call employee resource groups at Vertafore. They are executive-sponsored, but employee-led, so we can create as many of them as we want. It’s usually around groups that have shared interests or shared experiences. Those groups bring in their own speakers. They bring in speakers inside the company and outside the company. They talk about challenges. They make recommendations to the organization. That’s much smaller group conversation, which I think is also really helpful. What I love about our employee resource groups is, because they’re employee-led, they’re very organic, they’re very authentic. It’s not a check-the-box initiative, it’s a very authentic, organic initiative that has access to me and my leadership team for feedback, experiences, suggestions, and ideas. It’s great.
Alan Fleischmann
How do you anticipate the insurance landscape to look in the next 10 years? In many ways, it hasn’t been disrupted as an industry in the sense that other sectors and industries have. But it is transforming, so that is a form of disruption. I think a big part of that is Vertafore being able to help drive innovation, drive efficiency and effectiveness for the ultimate customer. But how do you think the whole insurance landscape will change in the next few years?
Amy Zupon
It’s a great question. I’ll take the angle of the distribution channel — where we primarily work — which is how you sell, market, and service the insurance products. When I first got into insurance six years ago, the conversation was, the independent insurance agent is going to go away. They’re going to be disrupted, they’re gonna go away. We didn’t believe it then, I didn’t believe it then, and I think it is largely understood now that that’s not the case. But that distribution channel is evolving, that distribution channel is transforming. These agents, what they do today in processing insurance cannot be what they do tomorrow. Their customers deserve a better customer experience and their employees deserve a more expedited, streamlined process.
So I think you’re going to see continued investment — there’s a ton of investment in the space today, technology-wise. And I think you’re going to see a lot of investment in how that channel works, trying to automate some of the things that have been traditionally manual for many years.
Alan Fleischmann
What would be your advice to those who might be looking at Vertafore and the industry that you are a leader in? How would you describe why this is a great opportunity and why they should be part of it?
And then, what advice would you give to young people? Especially women, I would argue. Because you’re such a role model, both as a CEO and as a leader, but also as a woman leader. What advice would you give to young people right now. Why is this such an exciting kind of business and the best is yet to come?
Amy Zupon
Honestly, I think we haven’t hit the tipping point of the opportunity. If you think about the technologies that are available today, if you think about the old-school legacy ways that things are done today, you can’t help but get excited about it. There’s money in the industry, there’s a need in the industry, there’s desire for people to solve problems in the industry. And there are problems. So as a software provider, as an entrepreneur, as a startup person, as someone who loves building products, it’s a perfect ground to come in and say, “Hey, we can tackle this right?”
My guidance for them would be, there’s so much opportunity to focus on real problems, not shiny objects. You can do cool things to do cool things; that actually doesn’t deliver value for business. My guidance to startups, my guidance to people who are getting involved in the industry is, make sure you really understand what problem you’re trying to solve and get laser focused on really solving that particular problem.
Alan Fleischmann
That’s great. What last bit of advice would you give to our listeners about navigating during these times right now? Imagine you’re talking now to CEOs, up-and-coming CEOs, and leaders who support those CEOs. Would love to get your last bit of advice for them as well.
Amy Zupon
This is always a hard question, because we all take our own journey, right? But I might answer it like this: when I look back on keys to my own personal journey, I say, have confidence in yourself, go after what you want to achieve, do it with intentionality — like, be intentional about it — do the hard work every day, and most importantly, never stop learning. I think being a lifelong learner and appreciating what you can learn from everybody about you is fundamentally key to your continued growth and success.
Alan Fleischmann
When I think about you, I think of you as being a confident CEO, but I also think of you as being one who combines confidence with humility. And certainly, a great deal of focus on the team that you built and are working with you every day in the trenches. How much is humility a big part of that? We talk about this on the show a lot: it’s the only way you can guarantee that you can live a humble life and be so grateful. Amy, I hear in your voice how you feel very grateful for the positions of power, the positions of authority, and the positions of opportunity that are given to you. But they haven’t been given to you, really; You’ve been working for them, and you’ve seized them as well.
Amy Zupon
Oh, 100%. I’m grateful for the people I’ve met along the way. I have learned so much from everyone, I learned so much today. I’m grateful for the people who show up every day. And I’m also proud to have the opportunity to do the same for them. To show up every day, to do the hard work, to do the coaching, to be the mentor. That’s an exciting spot to sit in.
Alan Fleischmann
That’s so exciting. You’ve been listening to “Leadership Matters” on SiriusXM and leadershipmattersshow.com. I’m your host, Alan Fleischmann.
We’ve had an amazing hour this last hour with an extraordinary CEO, Amy Zupon, who is the CEO of Vertafore. We’ve had a great discussion — not only about your career Amy, which has been so inspiring, but also the way you approach leadership with it. A lot of good advice today. So grateful that you joined us.
Amy Zupon
Thanks, Alan. I appreciate the opportunity.