PointClickCare’s Mike Wessinger on how Canada’s tech sector stacks up globally

Mike Wessinger PointClickCare
Newly appointed C100 board co-chair talks community building, fundraising, and talent.

Amidst the buzz of North America’s tech scene, where savvy personal branding often takes centre stage, one prominent figure embodies the timeless truth that actions speak louder than words.

Mike Wessinger, the co-founder of PointClickCare (PCC) and current board chair, is the first to admit he may not be a household name beyond industry circles. Despite steering PCC, Canada’s largest privately held software company, he’s still met with the question: “PointClick who?” It’s a reflection of his humility and belief in letting accomplishments do the talking, a trait he attributes to the Canadian spirit.

In his exclusive interview with Aly Gillani, Head of Canadian Tech Investment Banking at RBC Capital Markets, Mike delves into his advice for cultivating a thriving tech ecosystem that stretches beyond Silicon Valley and how to build tech unicorns in Canada (while still staying humble, of course).

Given your leadership role in the Canadian tech scene, how do you see the sector stacking up globally?

I think Canadian companies can punch above their weight. We still have an issue where we don’t have enough scaled companies and enough talent in the ecosystem for companies that are crossing over the $100-million revenue mark. We still struggle to find people in Canada who have had the experience of the larger-scale tech companies.

But I think that’s starting to change. A decade ago, before [PCC] had hit $100 million, we really had no choice if we wanted to find someone in the C-suite who was four, eight, 12 quarters ahead of us. We had no choice but to look to New York, Boston, San Francisco, or elsewhere in the States. Now, for companies that are smaller than $100 million in revenue, I think you can find those execs in Canada.

It’s still a challenge for those companies who have scaled to try to find local talent, but my rough math on this is that we just need to get to 20 companies over $1 billion in revenue and 100 companies over $100 million, and then we’ll have a self-sustaining ecosystem.

How did you achieve that success with PCC?

I think we came to the conclusion fairly quickly that what was important was getting the right people, and geography was secondary…which meant we had to figure out how to do our work with a dispersed team. As long as we could get them together often enough, it worked out all right.

When Covid hit and everybody was dispersed, it didn’t feel awkward for us because we had figured out how to work with remote teams before. Where we have settled in today is that we have people who are coming from multiple time zones, getting together about three or four days a month.

You’ve said in the past that you made a conscious decision to stay in Canada despite some pressures to move down south. How did you approach that?

I think maintaining control helps. Then there’s a little less pressure [to move], but you can see how this happens. We’re a Canadian-headquartered company, but 40 percent of our staff are in the U.S., given that 95 percent of our business is dealing in the U.S. healthcare market.

When you want to find people who understand Medicare, Medicaid, managed care, they’re probably not Canadian. You can imagine the pressure that you would get from investors when you’ve got most of your business in the U.S. and then it gets difficult to start finding that CFO, for example, and you can’t get them to move to Canada.

If you don’t control the company, at some point, your largest investor goes, “Well, why don’t you just move the headquarters to Boston or Washington or San Francisco?” But that was just never really an option. Dave and I are Canadian. We choose to live in Canada and there was never a moment where we considered going south of the border, even though it would have been easier to recruit.

Speaking of building community, what are you doing as co-chair of the C100 and how is the organization helping to promote these companies in Canada?

One of the roles I think the C100 can have in the ecosystem is doing a better job of telling stories from companies that aren’t telling their own stories well enough, and really promoting them.

At the core, we’re trying to get a network of great Canadians in tech and help them to support each other. Whereas, in the Valley, every coffee shop you go into you’re probably going to bump into five tech billionaires. Well, in Canada, we’re pretty dispersed.

So, I think the role C100 is going to play is connecting and weaving that network together not only across Canada, but having it plugged in with the Valley where there are a ton of Canadians that are plugged into the epicentre of tech. And I think if we can do that, connect those Canadians together to help support each other and tell our stories, I think that will go a long way towards promoting the Canadian tech scene.

How has the funding environment evolved in Canada? And do you still think it’s a challenge?

I think by the time you get to Series A, it’s a global market, and you’re going to get all the best private equity firms from across North America. So, I don’t think that’s the issue.

I think the issue in Canada starts at the seed and pre-seed stage. Because there’s not a lot of competition in the seed and pre-seed market, it really is a local game. It’s like Toronto, Montreal, Vancouver.

You don’t want someone from three time zones away who’s going to write your half-million or million-dollar check…[because] you wind up with a difficult decision. You’re like, “Wow, I just got this term sheet that is honestly a 60 percent discount of what it would be if I was in the Valley or in Boston. This is ridiculous. ” So, they either take that money on miserable terms, and by the time they get to Series A, they probably lost control of the business. Or they go find alternative money, some angel investors where they wind up with the wrong people guiding them.

I’ve run into a number of these companies and the 101 of how you build a startup is sort of missing because they’ve gotten the wrong advice. So, I think if we can solve that problem and get more competitive term sheets for seed and pre-seed, they can get to their Series A and still control the company, they’re going to get all the best private equity companies from across North America showing up for them. But they really need to get out of the gate with better terms.

We’ve talked a lot about the downsides; what are some of the upsides of building a tech company in Canada?

As I see it, we’ve got incredible talent. I just talked to our Chief Product Officer who had spent years working for many tech companies, and he will tell you that bar none, the best talent he’s ever worked with…are the people that he’s hiring in the GTA.

We’ve got an incredibly liberal immigration policy, which helps us. If we identify somebody on the other side of the globe, within weeks, we can have them working at PointClickCare, and you don’t have that south of the border. We get incredible talent, proximity [to the U.S.] and I think other than the early seed and pre-seed funding area, all those private equity companies and venture capital companies have figured out that there are some great companies in Canada, so they’re showing up. It’s not a well-kept secret anymore.

What is your advice to the next generation of emerging tech entrepreneurs?

Just go for it. There was this notion that entrepreneurs are risk-averse in Canada, but I think if you’re looking at the Valley, they just go for it because there’s a foundation and infrastructure in place to do it. So, I think that that’s good advice.

Aly Gillani

Aly is a Managing Director and Head of RBC’s Technology Investment Banking group. He has over 13 years of capital markets experience, primarily focused on M&A, equity and debt financing for technology and media companies. He has led a number of technology transactions ranging from $50mm to $5bn in size across various sub verticals including Software / SaaS, IoT, digital media, Internet and FinTech. Prior to joining RBC, Aly was a Senior Manager in Blackberry’s Corporate Strategy and M&A group. Aly holds a Computer Engineering degree from the University of Waterloo and an MBA from London Business School in the UK.

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