In this episode of The Heidrick & Struggles Leadership Podcast, Sean McLean speaks with Dave Wessinger, co-founder and CEO of PointClickCare, about the leadership journey behind one of Canada’s most successful global growth stories. Dave shares how he’s navigated key inflection points over more than two decades, from identifying which skills to develop personally to knowing when to bring in external talent to scale effectively.

The conversation explores how PointClickCare has maintained its purpose-driven culture and the company’s thoughtful approach to global expansion. Dave also reflects on how he views AI as both opportunity and disruptor, the ongoing challenges of return-to-office in a post-pandemic world, and the advice he’d offer to founders aspiring to achieve lasting impact and growth.

Below is a full transcript of the episode, which has been lightly edited for clarity.

Welcome to The Heidrick & Struggles Leadership Podcast. Heidrick is the premier global provider of diversified solutions across senior-level executive search, leadership, assessment and development, team and organizational effectiveness, and culture shaping. Every day, we speak with leaders around the world about how they're meeting rising expectations and managing through volatile times, thinking about individual leaders, teams, organizations, and society. Thank you for joining the conversation.

Sean McLean: Hi, I'm Sean McLean, partner in charge of Heidrick & Struggles Calgary office, and a member of the global Industrial and Financial Officers practices. My guest today is Dave Wessinger. He's the CEO and co-founder of PointClickCare, a multi-award-winning healthcare and vertical SaaS company and market leader in senior care electronic health records in the most expansive clinical network in North America.

Dave, thanks so much for joining us today. 

Dave Wessinger: Happy to be here. Sean, you sound very official. 

Sean McLean: Yes. Let's jump into a conversation with that intro behind us. Dave, PointClickCare, or as I've heard you refer to it, PCC, is that elusive Canadian unicorn. I'm sure our listeners would be interested to hear the origin story of PCC and how it evolved to become the dominant player that it is today. 

Dave Wessinger: OK, well, I'll do my best. We had started this just before the dot bomb dot com, and what's interesting about the founder story was that you know, if you get close enough to a problem that you have a desire to go solve, which I did—I fell in love with the problem, my brother did as well, and we decided we wanted to change something for the better. That was the catalyst for us to go do something different than our day jobs, which were fine, but they were the formative years of us understanding a problem more deeply than anybody else and recognizing we could do something about it.

Probably the hardest step, as I look back, is actually deciding to make that change. You know, I go back to the early days as well, and it's not like we had lots of time on our hands. I think I had one child under one, one on the way. I was living in a townhouse, commuting an hour and a half into Toronto every day.

And it was like my brother and I—actually randomly enough, it was a winter snowstorm. I was on my way downtown and I stopped by his office because I literally couldn't make it in. I'm like, “Well, I'll just work from here for today.” And that was the day we had the conversation about [it, and asked ourselves,] “Are you prepared to do something differently?”

I shook hands with Mike [Wessinger] and I said, “Yeah, let's do this thing. Let's start this venture.” And he's like, “You know you're going have to quit your job.” I'm like, “OK, well that's a real job making real money; this better work out.” But it all started with those formative years: finding your problem you fell in love with and deciding that you have somebody dumb enough and young enough to come alongside you to do it. And what's better for that than a brother? 

Sean McLean: It's somehow perfect that this Canadian success story started because of a random snowstorm. I love that. Fast forward now, Dave. It's more than 25 years, isn't it? It’s fairly rare that a founder can break through all of the challenging inflection points that occur between the launch and then eclipsing that billion-dollar valuation. A multi-part question, I guess: what attributes or experiences did you naturally bring that were helpful? What did you need to develop to remain successful? And then what key talents did you need to recruit from external? 

Dave Wessinger: Wow, that's a lot there. I'll try to break that down. What's interesting about that growth is that I think founders have a unique ability to grow with a business, unlike many others. And what's interesting, that I don't think people pick up on, is you have an ability as a founder to not be questioned about intent. You're largely there because you love the business and you care about the mission you're on to serve the people that are using your capabilities. And largely you become friends or really connect with the people you work with.

So, it's just genuine and people follow that. And largely, they came here because of that. And so that was probably pretty natural and pretty easy to fall into. And continuing to care about what we do in the mission, I think, makes all the difference, quite frankly. And so, you kind of bring that founder pixie dust or magic.

Other CEOs may show up and it's like, what are they here for? What box do they need to check? Are they trying to go public? People always question that. They don't really question that with me or brother Mike. We're here for the reasons that are about growing a business, doing good in the world, and being good people.

That was kind of it from the beginning. Some of the skills that I think I've developed along the way are things that we all should be doing, quite frankly, and that is you just need to be curious. You need to have a growth mindset. Not having those things is challenging, to say the least, but if you're just curious and you want to learn, there's an abundance of information to help you.

Certainly, now with the age of information and where it's at and the ease of access, that certainly helps. But I'll share with you a point when I was stuck. We had decided to recruit some professional help into different roles, and I'm like, OK, well I'm this old founder guy, I don't really know this stuff anymore. I should just step aside and let professionals run our company. And I saw it happen: I saw our culture get eroded. I saw the team not be as motivated or inspired. We started to not perform quite as well. And I'm sitting to the side going, Gosh, is it really my time to move out of the way? This is about 10 years ago, Sean. 

I actually bumped into a professional behavioral psychologist, and she went through and we did an assessment. It was phenomenal. The number one thing that came out of that was her feedback that “Dave, you're not crystallized. You can still learn.” I'm like, “No way. Are you kidding me? I can still learn at my advanced stage?” She goes, “Yeah.” OK, well I've still got the energy, and I decided to jump back in, and, some of us write things down about what you're going to do over the next number of years, and I said, “You know what? I'm going to lead this company one day.”

Well, my brother Mike was CEO. I was supporting him as his right hand. I didn't really think that was going to happen. But there are some things that you write down that subconsciously, they just start to work their way out. So that took a few years. I worked my way into leader, just taking over more of the organization in terms of responsibility, and then got my way into, gosh, it'd be nice to run this business. My brother had been CEO for about 20 years, and I realize now—it’s clear to me that he tricked me into this role. It is a really hard job that doesn't look hard on the surface because you literally don't do much. You create a lot of work; you don't do a lot of work. But you're constantly under fire, under pressure, for a lot of reasons, in a lot of ways, and it's pretty lonely actually. I don't think people appreciate how lonely it can be. 

It's just continuing to develop, continuing to learn, grow. Never feel like you know more than the market or feel like, you know, I have all the answers. That's kind of the exact wrong approach. Just be curious to learn, and that journey will take you to a lot of places. And for me, it's allowed me to continue to lead this business and feel like I'm doing it a service versus because I'm a founder I have a right to it. 

Sean McLean: I've been excited to broach this topic with you. My observation is that Canadian companies either struggle to compete internationally or just get acquired before they even get a chance to try. How has PCC been so successful in expanding beyond Canada and is there any advice you'd give to others? 

Dave Wessinger: It's interesting. I've thought about this a lot. There's a piece, as I look back on our story, there's certainly lots of good thinking that went into growing our business, but there's also luck along the way. It's just inevitable. You can't get everything right, and sometimes things need to fall in your favor. 

I think what was interesting about Mike and I, just being honest, we basically were poor. We didn't have any expectations. We weren't making a lot of money. It wasn't about all the great wine we were drinking or all the great places we traveled to. It was about solving this problem and doing something that was a little beyond just local. And I think without having those needs and that desire to say, “Let's chase an A round and a B round and a C round,” we were self-funded. We're like, “You know what? We don't have anything. We don't need anything. Let's find a way to leverage our customers to find a way to invest in us and kind of prepay subscriptions so that we can invest in the solution. They'll end up paying over time, but we will leverage that as common initial.” We didn't give away the business; we just gave away subscriptions that they would eventually get at a discount for a period of time. And so being innovative in how we went to the market allowed us to not give away our business. When we did take money eventually in 2011, it was minority [shares] because we still wanted control, we wanted to make decisions that made sense. And back then, nobody would invest in culture, and we felt that was really important and we weren't prepared to give that up.

So that's one way. But the other thing which has dawned on me recently is this economy can't handle and can't support billion-dollar business failure. There's just not enough here. So, for us, the revenue from Canada is low single digits relative to our total revenue. If we had to invest hundreds of millions of dollars a year in R&D, we couldn't do that with this end market, so we quickly realized that we had to go south into a larger kind of population or TAM, total addressable market, to go and help this business survive and get the investment necessary to drive good outcomes across the markets we serve. 

What's interesting is to innovate in Canada, you almost have to go somewhere else first to get the revenues and grow the business so you can come back and address the business problems here in a way that has the resources necessary to deliver on the problems that we need to solve here very differently. So, I think we got lucky with that, but it would be very hard for us to sustain a business just with this end market. 

Sean McLean: There's something inherently Canadian isn't there, about growing conservatively, growing through cash flow versus going out for external capital so early, and it's a real strength of Canadian companies. We saw it during the global financial crisis with our banks. It can also be a constraint on growth. It's really interesting that PCC has seemingly found that sweet spot of when to go external, how to structure it, and having the ability to dictate those terms more than you would if you were early stage. There's always that tension between driving financial results and patient care, especially for the front line. It can become an important cultural question that goes right to purpose. How does PCC walk this tightrope and how does it impact how you think about talent acquisition and development? 

Dave Wessinger: I'll get to the latter in a moment. The second we look at our finances over patient safety, patient health, and delivering good outcomes is the second we shouldn't exist. One gets the other. It always does. And for the longest time, you know, I never really looked at our financial statements. Not that I didn't care, but that wasn't our purpose. I knew we'd be OK if we served the market well. If you take care of your customers, if they end up running a better business, you will always be OK. 

This hasn't been more true for us then when I look back to Covid, and I love it because we got to pick, and this is kind of another piece of advice that I would share for anybody going down this path: make sure you're really thoughtful about who you bring to the table  from a PE or a VC because their opinions matter and you want people that can partner with you. For us, this was evidenced by getting into Covid, and this is where when things are going well, you never get a chance to test your true colors. But when things start to go south, it's when the real personalities come out. It's where the real alignment could go awry. And I remember sitting, and it was very gray. Nobody really knew. AI feels a little bit the same way as Covid, by the way, but it was like nobody knew what to do. There wasn't a pattern of “Here's how we need to get through it.” And you had to learn every day. We quickly realized that the right thing to do is pull back our sales team and stop selling to our customer base and start supporting them. And two things happened. We got on with the board, we talked about it, and it seemed like the right thing to do. Why wouldn’t you? I mean, your brand matters. The way you connect with the customers is important. That makes sense to us. We didn't have a conversation about the financial impact.

Others would have a very different appreciation for that. But the people we brought to the table were very well aligned with our mission and how we thought as founders to the point where we said, “Listen, if anybody on our team wants to go back into the field (because we have a number of healthcare professionals that left the field to work for us as a software company), please feel free to go back to your community. Just let your manager know so we know where you are. But go back to your community. Serve that community. We will pay you in whatever role you decide to be in, just let us know when you're coming back.” Not many companies would do that. But that's not just a decision I can unilaterally make. I need support for that, which means I need a leadership team, and I need a board that have an align on the same values.

That to me is what makes us unique and different in that we are more about doing the right thing than doing things right. And that came out in spades during Covid. 

So, as it relates to recruiting, the big thing for me is obviously a growth mindset, people that really care about what we do. I'm not here to hire mercenaries who will last but a period of time. It's about “Do you want to do well in the world? Do you want to have an impact? Do you want to work with other smart people? Do you really give a shit?” Right? Does it matter? And then I ask the really challenging question, which is “Why PointClickCare? Of all the things in front of you, why us?” And you can't even imagine Sean, the kind of answers I get to that: “Well, I think you're going IPO, and I can't wait to jump on that trend and get a huge payday.” Next; right? That's just not for us. 

So, align with our mission and our values. Just be a good person and show that you can demonstrate how to learn; be a good athlete. How do we float all boats across the team? That's how I think about the team. That's what I care about. And everyone has a different way about them—that's just how we operate here. The people working for you are a reflection of how you want to operate.

What kind of business do you want? If you run after talent but don't care how they operate, then you're going to have a faction that is fighting your culture. 

Cultures and values aren't about “Let's opt out on people.” Of course, we want diversity and perspective and different things, but there are people that will work for companies that are driving financials over anything else, and folks that really care about the people they serve and the mission they're on and may have had an experience with caring for someone who's dealt with the health system. That makes a difference. And the second you've been touched by that, you're like, “This means more to me; this means a little more to me.” All of that allows us to show up with a little more passion, a little more caring, a little more empathy. And I think as a business, that's just what we've chosen to be. And that shows up in how we serve the business and the very challenging end market that we have an opportunity to serve, and I feel responsible and privileged to be able to do that. 

Sean McLean: You've partially answered this next one, but I want to go to it anyway because I think founders will be particularly interested in your answer. Private capital activity in Canada has increased dramatically in the last 10 years, and yet many founders remain hesitant to take on a financial sponsor. What advice would you give to founders who have private capital firms starting to knock on their doors? 

Dave Wessinger: It's going to be a long ride. I mean, they're going to call you every quarter. They're going to ask you what your numbers are going to look like, where you're going to be, what you're going to do, and they'll do it over and over and over and over again and establish a track record on you, at least depending on how long you wait to take cash in.

In some cases, it's hard; you need to go after it. The only advice I'd have is kind of what I said earlier, Sean, that you need to make sure they have a similar playbook to the one that you want to run with. And so, if they're like, “We're here for two years and we're out—we're just making a quick buck;” great. That may be what you want too, and that's OK. Or you may want kind of a longer, more thoughtful partner that's like, “I'm not here to bruise the banana. I'm going to sit on the outside, let you guys run the business, do the thing, or, I need to get involved and push.” There's a lot of questions you need to ask to get there and then you'll get a level of comfort with them.

But the key thing to getting to that point, to getting to a value that makes sense to you, is to share with them honestly and transparently how you're performing. They want to know the good, they want to know the bad, and they're going to learn you just like you're going to learn them. So, it's a relationship I think you're building, and I think I would think about it that way versus a transaction. A lot of people get really caught up in that initial term sheet, that valuation. Oh, it's 225 pre-money, or it's 150 pre-money. At the end of the day, they have the same interest as you, so make sure you're aligned. Make sure you have a very clean term sheet that favors you as much as you can. I'd take that over more money in an unfavorable term sheet. Be really thoughtful of how you're going to be impacted by it, and partner with one that's going to make you better. Because it's all going to feel really good and you're going to be the Cinderella of the ball, right? That's what happens when you get through these things. Egos get big and you can't get through your front door when you're done them. I would just say really get aligned. If you have multiple shareholders, get aligned before you go down that path and know what you're really looking for because it's very easy to chase the money, and it may be the wrong thing for the business in your long term income. 

Sean McLean: You knew we had to go here eventually. AI is obviously a hot topic. How are you thinking about AI? Is it a threat? Is it an opportunity or something completely different? 

Dave Wessinger: Well, the one skill I think I've had is that I've always been super paranoid. I say that because we were the disruptor in the day, so we caught the cloud wave. We didn't really realize that wave was there, but we just knew something that was different, and we hopped on and we went faster than anybody else. AI is something that everybody is aware of, probably hyper paranoid about, and it's affecting all of us in a variety of ways. I think it's all of those things, Sean. I think it's a threat; it's an opportunity. There's disruption, and there's an existential threat to humanity if we aren't paying attention. The thing I would share with everyone is if you think the job you have today is going to be the same in six months, you're wrong. So, all of us need to get into that growth mode and figure out: what is the job I need to work into? There's a little bit of time to figure that out, but not a lot. We all have to move fast on it, and I think in the end it all comes back to “Are you solving business problems better at a lower cost?” It's the basic economics.

Don't get caught up on AI for AI. You really have to focus on the business benefit that's realized through AI's potential. And of course, we're all going to be, you know, human in the loop and then automating in some things. Our world is changing. We all have to adjust to that, both in how we run our business and how we serve our customers. And the more on it and the more educated and the more aware you are, the better. Putting your head in the sand will be like all the other ones who didn't catch the last wave. This one will be more meaningful.

I'll use an example: it took us 25 years to build the platform we have today—a bunch of products, a bunch of capability, all fine. Let's just say we get a dollar per month from a customer. There is one AI solution that we've positioned to the market that in the end—it doesn't even matter what it is—but the exacting value that comes from the work we're doing, that will probably take anywhere from three to six months to get through it, and we're probably halfway through it, it will end up going to market and they will pay largely closer to two dollars per month.

So, we spent 25 years building this platform, which is now largely becoming a database to AI agents, if you will, and you can build on top, but you can deliver so much immense value with AI that they're prepared to pay double what took me 25 years to build. It just gives you this new sense of there is so much value up here, that you're disrupting and changing the whole model on their end. It's not the same old; it's all very different. There is a ton of opportunity for all of us out there if we think a little bit differently, which is: don't think about building for humans. Think about building for humans in the loop or building for more automated work. It’s a very different way to think about solving a problem, and if you don't understand the tooling and capabilities around AI, you may solve the problem with the wrong set of tools and find yourself on the outside, not on the inside. It’s a challenging time for all of us. And if I told you I feel super comfortable, I'd be lying to you. I'm a little bit nervous and super excited at the same time.

Sean McLean: From a hot topic to a topic that has been somewhat stubborn in sticking around: return to office. Software, and many other companies, were pretty successful in transitioning to work from anywhere during Covid. Transitioning back to more people in the office has been harder. Where are you on this topic?

Dave Wessinger: I'm working down a path of what's right for PCC and what I think is that I treat people like adults. I don't treat them like the lowest common denominator of the worst person of the worst place of the worst area. Let's put policies in place to protect against that person. They just shouldn't be here. But everybody else is an adult. They're responsible. They care about my business. They work hard, and the more I give them, the more they'll give back. Very basic stuff, right? It's not that hard to figure out. If you treat people well, they'll treat you well. That's just the premise of how I think about it. But I would go one step further and say that there are moments that matter, and that's how we're thinking about it. When you get onboarded, you should be surrounded by people, see the culture in action, physically be in place and learn from, connect, and grow, and get attached to your team faster, and learn and build relationships. That's really hard to do 2-D, talking once every other week, so that's one piece. The other thing I think about is there are times where I need to collaborate with a team. That's always better done on a whiteboard, in person. You can literally see how people are reacting to the idea walking out of the room, right?

And then I think there's another piece which we don't quite have a perfect script for yet, but where I just want people together—where when I get my executive team together, we're trying for about a week, a month, and the intent there is generally if I want to meet with my president and my CFO, it's like, “OK, let's get them on the schedule.” “Calendar's busy.” “Well, let's do next week.” Actually, I just want to talk to you for five minutes, so I walk out of my office: “Hey, do you have a minute?” “Yep.” Boom. Done. So, the speed at which we can move by having access to each other. If you can simplify the hybrid work where we make these remote meetings a little easier, but everyone's calendar gets full when you're at home.

Every one of my employees has an opportunity to spend a week, a quarter, at whatever office they want to. Make a good choice, try to be with your team, try to get there when there's more people there. I trust you as a person to make a good decision.

So, in the end, we've all adjusted to a lifestyle that forwards us a fair amount of flexibility, which I think is amazing. And I want to continue to give that to my team and find a way where we don't lose speed as a business. And those aren't necessarily in conflict with one another, like others believe.

I think we have a great team, and I'd rather give them the tools to perform well than mandate anything.

Sean McLean: I want to wrap up with some advice from you to founders. I think by any measure, PointClickCare would have to be considered one of the biggest success stories in Canada in the last couple of decades. I want to share something, having worked with you and a few other successful founders across Canada, there's always some version of “We became an overnight success after 15 or 20 or 25 years.” The early years are grueling. They're hard. The lean years are very lean. The size of the risks, the swings were big, and it's easy to look now at PointClickCare and a handful of others and see it as just this glamorous, incredible thing to be a founder, but the early years are very challenging and do have risk.  Kudos to you and your team for navigating all of that. I just say that to founders before taking the plunge: it's a tough road. What advice, and you've given us a bunch today, what advice would you leave us with here today to founders aspiring to achieve what you have?

Dave Wessinger: Yeah, it takes a lot of courage to go do it. So, anybody who's thinking about it, who’s in the throes of it, or might do it, hats off to you for doing that. The other thing I would say is, be careful of spending too much time in the analysis phase because you'll find a way to convince yourself not to do it. And, if we were to share our business plan with anybody prior to doing it, there wouldn't be a single person in the room saying, “You should go ahead with that. There is a fully saturated market fully served by other vendors. Why would you go into that space? And they're better than you and stronger than you and make more money than you.” We were like, “Well, we think we can do it differently.” You couldn't talk us out of it. You have to have conviction. You have to believe in it.

If you believe in it, people will follow you. It's not like they bought the better thing from us. They just believed that we were going to solve the problem differently than anybody that's come before us and were prepared to follow us. They're buying you. That's my biggest advice: they are buying you; they're not buying your product. Initially, it's all about you: how you show up, your beliefs, how you serve the market, and do that well and do it quickly. It's not like you need 10 years to build these things. But I would say just be very focused, very committed, very open. Surround yourself with people that you know, like, and trust that will challenge you.

I got very lucky in that my brother and I were two middle children of four brothers, and obviously we're the pleasers, and it was easy for us to go head-to-head and have really challenging arguments, and we'd have some teammates around us saying, “Wow, are you guys going to fight?” And we’d say, “What are you talking about? We’re going to go get a beer now and hang out.” It was those kinds of courageous conversations. All this other stuff came after. We have to be able to put the stuff on the table and be OK to talk about it and then move away. 

But you need to have some people that are prepared to be with you, that can work along with you and challenge you. Have conviction. Surround yourself with people that will challenge you and help you down that path. And you're going to question yourself a lot. You're going to be, “What the hell am I doing this for? This is the worst thing I've ever done.” There's a chance you're going to fail, but there's an even greater chance you're going to do well. Keep being optimistic. Keep serving your end market. 

I'll share with you, Sean, one more thing, and this is why I think having a partner in crime is really important. Being the engineer side, I wanted to get everything right before we scaled. We had deals that were coming across, but I said, “Nope, nope. Can't do it. Can't.” And Mike's said, “What? What are you doing?” I said, “We're too busy. We can't serve all these people.” He said, “Take the business and we can apologize later. If we don't take the business, we won't be around later to apologize.” And believe me, that was a four-hour meeting, and you know, we were probably throwing stuff at each other and freaking out. But that's the kind of discussion you need to have. If I was on my own, you wouldn't know about us today, but having someone on the other side, challenging and asking questions and getting to a good answer because we literally could put the elephant in the room on the table and talk about it and make a good decision.

And the other thing is to use some playbooks. You're not the first person to do this. We were big Geoffrey Moore fans crossing the chasm inside the tornado. We lived those books. I promise you, I feel like we wrote it with Geoffrey. We've gotten to know him since; he’s a wonderful man. But there's lots of opportunity to learn. There's lots of people that have come before you that can be helpful, so lean into that and become a student again of all of the artifacts out there that will help you make great decisions. And sure, AI has made that a lot easier for you but use all of the above and reach out to a network of people that you can just connect with and learn from. I would take advantage of all of those wonderful, generous people—of their time. Be a student again. Learn. Love what you're doing and go solve it better than anybody else and don't look back. 

Sean McLean: It's a pretty powerful recipe, Dave: conviction, a thought partner that'll challenge you, and be a continuous learner. It's great advice. It was such a privilege to work with you for the time that we did, and to be some small part of the PCC story.  With all the things I observed and learned on that journey, I wanted to get on this platform so others could hear how you think about the PCC story, and it certainly has delivered. You've delivered. Thank you very much for taking the time today. It's been really enjoyable. 

Dave Wessinger: I appreciate the opportunity.

Thanks for listening to The Heidrick & Struggles Leadership Podcast. To make sure you don't miss the next conversation, please subscribe to our channel on your preferred podcast app, and if you're listening via LinkedIn or YouTube, why not share this with your connections? Until next time.

About the interviewer

Sean McLean (smclean@heidrick.com) is a member of the global Industrial and Financial Officers practices; he is based in the Calgary office.