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Ryan Davis, CEO of CINC Systems, on Accepting the Unknown

May 31, 2023
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AvidXchange CEO Michael Praeger interviewed Ryan Davis, CEO of CINC Systems, in the latest episode of “The Power of Change” podcast. The two discussed Davis’ unique path from news reporter to C-suite executive and how he’s guided CINC Systems through digital transformation and exponential growth.  

“The Power of Change” features interviews between Praeger and industry leaders who embrace change and use it to their professional advantage. Listeners learn tips on how to accept change and navigate the related challenges.  

Continue reading for a summary of the podcast or download the full episode now 

Using Storytelling to Communicate Through Change

Adapting to change is essential for business and personal success. Throughout his career, Davis has encountered new and unknown situations that required him to adjust and acclimate quickly. He often leverages his experience in journalism to help his teams accept and embrace organizational change.   

Davis shared that when he needed to rally his team during a time of rapid growth and infrastructure changes, he flexed his storytelling muscles. He also made sure to listen to the stories of his team to understand their unique viewpoints.  

“I pride myself on being able to tell a good story about where we’re going, a nonfiction story. And then maybe that’s the journalist in me realizing you need to tell it over and over again because it’s easy in the day-to-day to get lost. The second part is just listening. And maybe that’s the journalist in me, too. When I came [to CINC], I sat down and literally talked to everybody who worked here. It didn’t take too many questions to hear that people here wanted to change, too.”

Leaning in to Digital Transformation

Digital transformation is a major priority for many businesses today. It refers to the implementation of technology across the business, making internal processes more efficient and customer experiences more satisfying through digitization.  

In some organizations, employees may be resistant to digital transformation as it can change the nature of their roles and day-to-day tasks. In the case of CINC, Davis found it essential to meet growth goals. He believes that transparent communication is what helped get CINC’s employees on board with its digital transformation initiatives.  

“We’re fortunate to have a great company that had an opportunity to grow, and we just needed to do it the right way. My starting point is always the transparent sharing of what I want to accomplish. ‘Look, we have a great product. We need to figure out more of what our customers want and how we can serve more customers.’ I [had to] paint a mental picture through transparent sharing here. What I’m most proud of is the people – they’re the ingredients that have made this change work.”

Flowing Through Life’s Phases

When asked about the best advice he’s ever received, Davis said, “Enjoy each phase of your work or your life outside of work for what it is. And focus on what’s most important.” Even when situations are less than ideal, Davis has tried to make the most of it.  

Davis said the common thread running through his career is dropping into unknown situations and figuring things out as he goes. In both his personal and professional circumstances, he tries to embrace the present. 

“You look around at the pool sometimes at a resort, and you see two people trying to have a relaxing time and read a book and they’ve got their three kids running around. It’s like, ‘You’re on the wrong trip!’ I am well aware when I go with my three kids to the pool, I’m not going to be able to sit down and read a book and have a drink. So, I try to enjoy it for what it is.”

Since Davis started with CINC almost three years ago, the company has tripled in size and introduced a number of powerful tech tools to better serve its community association management (CAM) customers. As part of these efforts, CINC’s partnered with AvidXchange to deliver CINC VendorPay Powered by AvidXchange, the first fully integrated accounts payable (AP) solution for CAM businesses.  

Davis commented on the partnership and how it will help streamline AP processes for customers. “It’s a great partnership for both of our companies, but most importantly for the mutual clients who will be served,” he said.  

To learn more about Davis and his journey to corporate leadership, listen to the full episode here 

Check out more “The Power of Change” episodes as well as our other programs by subscribing to the AvidXchange Podcast Network. We’re available on popular streaming platforms like Spotify, Apple, iHeart and  Stitcher. 


Complete Transcript

Please note: “The Power of Change with Michael Praeger” podcast is designed for audio consumption. Transcripts are generated using speech recognition software and may contain errors. Please check the corresponding audio before quoting in print. 


Welcome to The Power of Change, a brand new podcast series produced by Avid Exchange. I’m your host, Michael Prager, the CEO and co-founder of AvidXchange. And my goal with this podcast is to bring insights from business leaders who embrace the power of change to fuel of their careers and transform their businesses and organizations. Each month, we bring you a new interview and actionable advice to lead your business through change and power your own professional journey?  

Our guest in this episode of “The Power of Change” is Ryan Davis, CEO of CINC Systems. Ryan is a longtime tech executive with experience that ranges from major metro news outlets to consulting firms to digital marketing and advertising powerhouses. CINC Systems is a largest provider of SaaS solutions for the community association industry and currently serves more than 20,000 homeowners associations and over 2 million homes. 

In my conversation with Ryan, we cover his journey from a newspaper reporter to CEO, unpack strategies and how to lead massive transformation for your organization and discuss the impact of technology on both the community management industry and Ryan’s personal journey as a business leader.  

All right. So Ryan, let’s start with kind of your current role. I believe you’re about three years into your current role as the as the leader of CINC Systems and maybe provide a little background on CINC Systems and kind of the mission, how you got started and kind of your role within the company? 



Yeah. So, I’ve been fortunate enough, as you said, to be here for almost three years. CINC Systems, we’re a fast growing software company that provides all in one software for the community association space. We’re fortunate that we’re by far the largest provider to this space.  

From a mission perspective, it is our goal to make it a great experience to live in a professionally managed community association. And we do that by providing the best tools to association management companies in this space, honestly, that’s been completely underserved. And those tools are, if you really think of it, put them into three buckets. 

You’ve got tools for banking, so these companies need to be able to take in payments from homeowners seamlessly and then get that information out of the bank and right into their software. So we were built on deep bank integrations.  

The second is accounting software. If you’re going to take, you know, ask homeowners to make payments, you need to be able to show them what you’re doing with that money and have accounting software that provides a very transparent reporting that you can get to people in the first five days of the next month. 

And then management tools to do with what a lot of us think about the community associations doing, which is architecture requests, amenity reservations, violations, if someone’s not keeping their space well, etc.  

So those three, you know, banking, accounting, management tools are the full suite of the all in one software that CINC offers. And we’re proud to be the leaders in that space. 



So, you know, within the HOA community management type space, it’s a pretty large, you know, market. And you get, you know, very small management companies all the way up to some of the, you know, the big gorillas. When you think of kind of your sweet spot of the market, how do you guys define that? 



Yeah. So we’ve built the software, so it scales very nicely. So we serve management companies from 20 or 30 HOAs all the way on up. We have clients with thousands of HOAs. So we have intended it for it to be scalable. If somebody has got less than 20 or 30 HOAs, it’s probably going to be getting something a little bit more than they need for what they’re trying to do at that point.  



Well, terrific. And you certainly have emerged as the overall industry leader. But before we talk more about, you know, CINC System and some of the impact that you’ve had, let’s talk more about, you know, Ryan, so you’ve had a pretty unique journey. You know, love to kind of learn a little bit about that, you know, journey of, you know, going from, you know, a journalist to a media executive and now the CEO of a fast growing, you know, SaaS company. Tell us a little bit about your personal journey. 



Yeah. Now, thanks for asking. I will say, you can tell the story from a gathering of skill sets, or you could tell the story from what I got hooked on that kept me here. So, I’ll give you both in abbreviated fashion.  

If you think about it, a journalist gets dropped into unknown situations and has to figure out what’s going on. And I had fun times getting dropped into parts of Baltimore that most people don’t walk through. We could talk about it another time, but my one of my first exposures, if you will, was covering a race at a clothing optional resort association in Florida. Getting dropped into unknown situations and trying to figure out … 



Support all types of customers. 



You know, I told our clients at my first user conference that the this was my first experience with HOAs. It was a clothing optional race at a clothing optional resort. There was an association. It’s only been uphill since then. It’s been good. Uou know, you get dropped into unknown situations. You got to figure out what’s going on. 

I spent time as a consultant where you get dropped into unknown situations. You got to figure out what’s going on and then you need to make a recommendation. But as you know from the business you’ve built, the most fun is actually making those recommendations come to life.  

So, the third part has been getting dropped into unknown situations, figure out what’s going on and then getting to actually, you know, make sense of that situation and lead a group of people to success. That’s the fun part.  

What got me going along the way is I was involved in the world of local media, and local media made its business on serving small and medium sized business as well. If you think of the local businesses that used to advertise in the newspaper and some still do, but, you know, used to advertise in mass in the newspaper. 

And the goal was to bring them an audience, help them market their product and help them grow their business. And, you know, when I transitioned to the business side of media, I regret that I didn’t have the answer for how to solve what’s happening in local media. I wish I did. It would be important for society. But I don’t have that answer. I don’t, Michael. I don’t have it. I mean, that would be a whole other podcast that we could talk about.  

But you meet these small and medium sized business owners who are, you know … Because of my roles over the last little more than a decade, you know, I’ve been inside the roofer in Wichita, the tree trimmer in Jackson, Mississippi, and the air conditioning guy in suburban Chicago, in basement waterproofer in Atlanta. I’ve been in their offices and they have so much in common. You know, so many of these wonderful business owners in many ways are living the American dream, but are struggling to get through on a day to day basis. They’re working in the business, not on the business. And they’re throwing people at problems that, gosh, if technology could solve it, they could live that American dream. They could have that efficiency. They could have a more profitable business. They could grow more. They wouldn’t have to be doing all the work themselves. And honestly, I got hooked on it. It’s a lot of fun to have clients who you can really help and you can see the difference you make. Not because you log into their quarterly earnings report to see that difference you made. It’s because you see it. 

My favorite moment in the entire three years I’ve worked here was last summer. I went to go meet a client and showed up and he wanted to chat and he wanted to do it over lunch and golf. And I showed up and the bill came for lunch and he said, “No, no, no, Ryan, you are not touching that. We wouldn’t be here if it wasn’t for your company. When I joined with you guys, I managed 75 HOAs and I’ve barely added any accountants and now I manage well over 300 HOAs and I wouldn’t be here if it wasn’t for your company. 

I personally am not taking credit for that. But our company, you know, but for our company and for the fact that we’ve made a difference in his life. He has a business he’s going to pass on to his son and his daughter now. And it’s a valuable business. And the fact that we’re a part of that, it’s just awesome. How can you not love being a part of something? 



And no, there’s nothing more fulfilling to seeing, you know, the firsthand impact that you have on a customer. And so those are special. 



This, you know, this space has been so underserved because there’s never been a company of any size – and size matters in software. It really does. There’s some places where it doesn’t, but it matters in software.  

And so painting this picture of being able to be a company that creates an unfair advantage for our clients and tilts the scales in such a way that they win and creates this great experience for homeowners. I mean, a lot of that comes down to just getting to the size where we can do things that no one’s been able to do in the space before. And they aren’t. They aren’t, you know, no credit to me for thinking of them. They’re employing what’s worked in other spaces, you know, where I think, you know, things like we have the biggest dev team in the space, right? 

We can do a lot more work, you know, a 60 person dev team, than anyone who’s, you know, had what we, you know, serve the space that we serve. And we have an account management team that isn’t there to sell. They aren’t there to answer the support cases. They’re to give proactive advice and be helpful. We have, you know, a support team that’s truly a support process as opposed to just a few people who know the software. 

We have a true product development lifecycle. I didn’t invent any of these and no one here did. But because they haven’t come to this space yet, we can give frankly, the space what it deserves. So, yeah, absolutely. It’s a whole lot of taking from other places, either other places I’ve been, other places our team has been, or just other places that are doing it well and are kindly going on podcasts or sharing it over coffee and telling us what they’re doing. And we’re happily grabbing. 



Yeah. You know, it’s interesting, you know, one of the things that I’ve learned over the years is that, you know, it’s like as a CEO or leader of a business, actually, you don’t have to really, you know, invent anything new. Just if you can recycle all the great ideas that others have had and kind of, you know, add your own kind of influence to them, you know, those worked pretty well. 

Well, well, good deal. So let’s go talk a little bit about the business and technology. You know, in your year, three years, you’ve really been a champion for technology. And maybe you tell us a little bit about your, you know, kind of your own within CINC Systems, the, you know, technology and kind of digital transformation journey that you’ve been on. 



Yeah, for us, I mean, this was a great company. I was fortunate to walk into what was already a great company. And for me, you know, I’ve walked into other situations where there’s probably more change required. Here, we’re fortunate to have a great company that had an opportunity to grow, and we just needed to do it the right way. 

But my starting point, and I love hearing other people answer this question because I learn every time myself, so I’ll throw my thoughts in and hopefully they mix around with some others and people can take something away from it. My starting point is always the transparent sharing of what you want to accomplish. You know, what is it you hope you can lead the group to?  

And if I can paint you a mental picture, that transparent sharing here at CINC, because I started at the very beginning of COVID, right in the heart of you know, we were just finishing wiping every box that came to our front door with Clorox wipes at the time I started here. And so my first sharing was in the parking lot at CINC Systems in suburban Atlanta. And the sprinklers came on as everyone was standing out there in the parking lot, gathered around trying to listen to me talk. So that’s the starting point.  

But it was it was a sharing of, look, we have a great product. We need to figure out more of what our customers want, how we can serve more customers and how can we can be ready to serve them. And painting that picture of transparency and then just reporting back and sharing those goals. 

 And you know what? I’m most proud of that I think is led us to, you know, when I joined here, you know, we’re three times the size. You know, we’ve created, you know, well over 100 more jobs. It’s been really fun. And what I’m most proud of, though, it’s the people. It’s the ingredients that have made this change work, have been that there hasn’t been a great technology company that serves this space, providing the kind of tools we provide before. 

So we can’t just go steal from somebody else and take those employees and go forth. So we’ve had to create this mix of wherever we can, we try to fill a role with somebody who has relevant experience from this space. And the one qualification is that they have a perspective on how this space, this community association space, could be changed for the better and that we could all do better. 

And then we try to bring in people with technology experience. But the one qualification for them is that they’re humble and they bring big ears so they can listen to figure out how to apply that relevant experience. You know tech folks, Michael, you can you can meet some tech folks who come with big egos. And that just doesn’t work here. It doesn’t work in this space. It’s not helpful.  

And we’ve created this wonderful mix of nearly 200 people now who you know, you’ve got these folks who know the space and one want to explain how it can be changed. And these folks who have relevant experience on how to do it. And that that that cocktail has been what’s fueled our success. 

And I guess I just add when I talk about relevant experience, the obvious question is what do we mean by that? You know, we hire mobile developers who worked for, you know, private jet companies where you reserved private jets. Well, if we’re trying to help people reserve amenities, that’s a pretty darn good amenity, right? You know, how do you make that mobile? 



How do I sign up? 



Yeah, exactly. We’ve got a, you know, a CTO and a head of implementation who came from the business risk software space where there’s a lot of data in community associations that you need to bring into a new software, but it’s nothing compared to what a Fortune 500 company needs to pick up and lift into their new software, and it needs to work the next day. 

So those are the kind of relevant experiences and humble folks that we’ve combined with people who knew the space. And yeah, there’s nothing I’m more proud of than that team and that cocktail that we’ve mixed together. 



So how did you know? What’s always interesting is what we found is, you know, the hardest part about any of this transformation stuff is the change and people kind of managing through change, you know. Any, you know, kind of secrets or kind of lessons learned in terms of kind of how you manage some of that change, you know, among your own team? 



I pride myself on being able to tell a good story about where we’re going, a nonfiction story, by the way, but a story. And then maybe that’s the journalist in me and realizing you need to tell it over and over again because it’s easy in the day to day to get lost. And why am I doing this? Why do I need to change what I’m doing? Why does it need to get better? Right? My team would probably tell you I tell the story over and over and over again, probably three or four more overs than necessarily everyone wants to hear.  

And then the second part is just listening. And maybe that’s the journalist in me too. But when I came here and sat down and literally talked to everybody who worked here, when I got here, it didn’t take too many questions to ask and listen and hear that people here wanted to change, too. 

It was getting hard. The company had gotten big, but we hadn’t grown up yet and we needed to grow up real quick because we were about to get bigger. And when I listened, people want their job to be easier, they want to feel like they can succeed. And we were able to put in place the infrastructure that enabled that to happen. And so that common thread of, you know, paint a picture of what you want to get to. But before you go paint too much of that picture, make sure you’ve listened to where the team wants to take it. Because the team had the answers. This team knew what needed to happen and where it needed to go. So it was it was fun to be, you know, thrown in front and say, hey, lead us. By the way, we want to go there anyways. Just help us get there. 


Well, hey, just in kind of in finishing up, there’s just a couple of questions about, you know, advice that you’ve been given. And so maybe you start by, you know, talking about maybe the best advice you’ve gotten, whether it be in business, leadership, personal, and where did you get it from? 



Yeah, I had you know, it’s coming combining a few things I heard. I think the best advice I’ve ever been … I love this question … I’ve taken the advice I got to apply both personally and professionally, which was enjoy each phase of your work or your life, you know, outside of work, for what it is and focus on what’s most important. 

For work for me that has meant when I got here, the biggest thing we needed to do was, was grow our team. And, you know, it was focus on building that team and laying the foundation. That’s very different than what I’m working on now and focused on and enjoying, which is making sure all parts of the company work together and that we truly are building the best company that serves the space and serves our clients well. 

But it’s the same thing in life. I have three kids and you know, I certainly enjoyed the phases that came before this without kids. But I’m in the phase now where the best thing I can do is spend time with my kids. They’re 13, nine and six, and they just want me in the way that they like to spend time with them. Whether it’s my Wednesday breakfast with my 13 year old daughter, you know, trying to assistant coach every sport I can for my nine year old son and, you know, doing worksheets of kindergarten with my little one and, you know, I my wife and I talked about this a lot. That’s what I’m most proud of. 

I think I’ve enjoyed every phase of my life for what it was. And it doesn’t mean it always went exactly the way we wanted it to. But yeah, I mean, you know, you look at, my wife and I still go away together, just the two of us. But then you look around and it’s knowing what you’re there for. 

You know, you look around at the pool sometimes at a at a resort, and you see two people trying to have a relaxing time and read a book and they’ve got their three kids running around. It’s like you’re on the wrong trip, right? You know, I am well aware when I go with my three kids and I’m at the pool, I’m not going to be able to sit down and read a book and have a drink. That’s just not going to work and, you know, enjoy it for what it is. And I’ve been fortunate there’s been a lot of fun along the way doing that. 



Absolutely. Well said. You know, for I myself have a 23 year old now and, you know, so I’m on the other end of the spectrum. But one thing I would say is that, you know, it goes by fast, but, you know, just you know, I’ve enjoyed every, you know, every phase of the journey. And, you know what I would say? It just keeps getting better. And now that, you know, he’s 23, we do adult, you know, adult things together and have really adult, you know, conversations and so, you know, this phase is great, too. So I would just say. 



He came right as you started the business, right? 



He’s yeah, exactly. He was born in November of ‘99 and we started AvidXchange in April 2000. So he pretty much grew up at AvidXchange and he’s interned at AvidXchange, you know, multiple summers as well. But he’s actually in San Francisco doing venture capital now. And so yeah, he’s doing well.  

Good deal. So you know so just a closing up, you know Ryan, just an incredible journey you’ve been on, you know, across your career, how you migrated to where you are today and I would say, you know, we thoroughly enjoyed spending some time with you on this podcast. And I think, you know, one of the questions, you know, that we’ll end with is, you know, through all this process, what’s the one thing that’s kept you the most grounded? 



So I’ll start by saying thank you for having me. It’s wonderful to be here with you. The company you’ve built, we’re so thrilled to be partnered with you. I think more and more details are going to be shouted about that publicly very soon. But there are a lot of folks who do know we’ve partnered together and it’s a great partnership, I think, for, you know, for both of our companies, but most importantly, for the mutual clients who will be served. 

You know, for me, I mentioned I have three kids. My youngest, my six year old, has a genetic disorder, an extremely rare genetic disorder. She was the 27th person in the world. Found to have it when it was found. And life’s harder for her. She can’t, she you know, we spent this weekend, you know, doing some kindergarten math problems together. It’s just harder for her.  

But man that girl gets out of bed every morning and she is ready to go get the world. And she is happier than any of the other four people in my house every morning when she wakes up. And she, you know, she opened a gift from Santa Claus this year and it was some math games. And she said Santa must see me in school and he knows that I need help. And so she looks at everything with such a blessing. You know, she’s getting a math game for Christmas and it’s oh, thank you so much, Santa is going to help me. I’m going to get better at math.  

She tells me every day why that day is going to be a great day when I wake her up. She tells me that today’s a great day, I’m having breakfast at school. None of my other kids have ever been excited about having breakfast at school. Things are harder for her, but man, she appreciates everything and that waking her up every morning and hearing that things she’s excited about that most of us forget to be excited about. I don’t know how you couldn’t just, you know, keep your two feet pretty firmly planted on the ground with that. And she’s such a blessing to me and I’m much better grounded in the six years I’ve known her than I than I certainly was any year before that. 



Well, that’s a good place to end this. And so well-said. And we really enjoyed having you. You’ve done phenomenal things with CINC. And from AvidXchange, we share your passion about, you know, the future together. And we’re as excited about the partnership as you are. So excited to kind of roll up our sleeves and begin, you know, impacting customers jointly together. 



And with that, I’m excited to have Ryan Davis from CINC Systems as our guest today. 



Honestly, we’re extremely excited about the partnership, thrilled to be working with you guys. And thanks for thanks for doing this. This was fun. 



One of the things that’s you know, it’s kind of interesting because, you know, I’ve been interacting with lots of different leaders. And one of the things I learned is, you know, one of the most effective leaders, they, you know, have the ability to really, you know, kind of present what the future state looks like. That’s usually a better state than where it is today. 

And so I was out in San Francisco in October. Reid Hoffman, he had his annual conference called Scale Up. He had both Bill Gates and Satya Nadella, current CEO of Microsoft, there. And they did a, you know, they called it their breakfast table chat. And Bill asked Satya, you know, it’s been a number of years since he become, you know, the CEO of Microsoft. You know, you get to interact with, you know, some phenomenal, you know, leaders across all different spectrums and, you know, is there anything that you’ve kind of taken away. And Satya, he’s like, yes. And there’s kind of one big thing that I’ve noticed that the best, whether it be world leaders, you know, or industry leaders do is that they’re able to articulate in really deep detail, you know, why tomorrow is going to be better than today and what the future state is. 

And they do it with an energy level that is very different than other leaders. And so I think there’s been a lot of learnings that I’ve taken away from that in terms of, you know, in uncertainty, you know, what people, you know, are looking for is what the future state looks like. And to be able to provide them context, you may not get everything right, but you know what that vision about our future state looks like, I think, is kind of that confidence that a lot of people need in terms of, you know, being led. 

Well, that will do it for this episode of “The Power of Change.” This episode was produced by one of my teammates, Travis Durkee. If you like what you’ve heard, make sure to subscribe to the channel and leave a five star review. Keep an eye out for new episodes each month with leaders from various industries. In the meantime, make sure to follow me and AvidXchange on Instagram and LinkedIn. Links to each are in the show notes. And visit AvidXchange for our latest research reports and business insights. 

So until then, remember, the best future is ahead of us. Make it a great one. 

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