Closing the distance for Canada's MSPs

She went to it as an operator at a growing MSP and came away changed, hooked on learning alongside the peers she met there. Carrie's instinct in a crowded room is to hang back by the wall and blend in (although her bright purple hair never quite lets her disappear). She's never been the kind to enjoy attention, an odd trait for a person whose whole job is filling rooms and getting people to talk to each other. Getting into the community, she says, "transformed my entire career, personally and professionally."

That is the through-line of everything she has built since. Across more than two decades in IT, through the shift from on-premises to cloud to security to whatever AI turns out to be, one belief has held steady for her - people learn best from other people. Community has shaped every major turning point in her career, and she is convinced it matters more now, not less, given the way AI is changing everything about the way we work and live.

The lesson that changed her career

Carrie's path to the CanIT Collective was neither planned nor linear. She spent her first decade in provincial government IT, left the field entirely when the growth stalled, and meant to retrain as a preschool teacher. She came back to IT almost sideways, joining a tiny MSP three years later as employee number three and relearning a field that had moved on without her. What kept her there was the people. "You never know what it's going to be on the other side of that phone," she says. "I love the people, I love the MSP model. You learn so much."

She rose to senior vice president of operations, and for a while the company ran well enough on instinct. Then, at an industry conference, she and her business partner sat in a room full of operators running the same kind of business, people willing to say out loud how they did it. They took what they heard home, rebuilt the company around it, down to how they priced and measured their work, and tripled the business in a year.

The lesson stuck, and it was not really about the growth. Someone had shown them what worked, and it changed everything. The breakthrough had not come from inventing something new. It had come from a peer who had already solved the problem in front of them.

That experience left Carrie with a question. Why was there no place for Canadian MSPs to learn from each other without crossing the continent to do it?

Building the community Canada needed

Gatherings like that are common in the US. "When you go to a US event, it's 90% US people," she says. Travel inside the States is easy. From Canada it often means a full day and a real bill. Operators in the US can find a conference or a peer group close to home without much trouble. In Canada they were few and far between.

The Canadian community existed, but it was scattered. The gap was partly geography. Canadian MSPs are smaller and further apart. A small group of peers traded advice informally and helped each other through problems.

Carrie remembers a friend in Utah telling her he had 42 MSPs within throwing distance of his office door. Where she is, it does not work that way. It was partly temperament too. Canadian buyers move slower and want a relationship before a transaction. "It's not just a transaction," she says. "It's more of a partnership, a relationship."

But none of this really stopped operators from helping each other. When Carrie was still at the MSP, they had a referral partner a couple of hours away, and when a client needed hands on a machine, someone to cycle a box or add RAM, they would call each other rather than make the drive. It went both ways, and many of those working relationships turned into friendships.

So, when Carrie and her business partner noticed that there was a market for building a Canadian version of what they had found in the US, they decided to just step up and build it. They had their first conference in Canada in 2023. What started as CanITCon has grown every year since and is now the CanIT Collective, a name meant to signal that it had outgrown a single annual event. "Meet, learn, grow," she says.

Why AI makes community even more important

That tagline can sound soft. The problem it answers is not. AI is the steepest change to hit the field in years, arriving on top of every shift before it, and Carrie treats it as one more turn of a wheel she has watched spin, from on-premises to cloud to security. She was slow to trust this one, and honest about why. "I wasn't scared of losing my position," she says. What worried her was information, handing over data when she could not see what happened to it on the back end.

She has landed in a clear place. "I don't think it will replace people," she says, "but I think it's going to enhance more than it's going to replace." The repetitive, mundane work can go to an agent. What is left is the part that needs a person. "As human beings, we crave that connection." Used well, she thinks, AI gives people more room to be present, not less.

Here is why she thinks community matters more in this shift, not less. Nobody has the playbook yet. "It's so new," she says, that you cannot simply look it up. MSPs are learning AI the way they learn everything in this field, by using it and by asking the ones who went first. That is what a community is for. People learn differently, she points out, some by doing, some by listening, some by talking it through, and she counts herself among the talkers. Certifications can set a baseline, but knowledge that is never applied stays just knowledge. The fastest way through is still a room of peers comparing notes.

What community actually looks like

A room of peers is easy to romanticize. What makes the Collective work is that the help inside it is concrete, starting with how the organizers treat the people they serve. "We don't just read the words, we actually implement a lot of it," Carrie says of the feedback they collect. Attendees notice when their comments turn into changes. "It's not for us," she says. "This whole thing is to better the MSP community."

The support runs well past the main event. This year they added roadshows, smaller regional gatherings that travel to parts of the country the conference does not reach. The west already knew them. The east less so, so they took one to Toronto, where 80 of the people in the room were strangers to Carrie. Between events, a Discord server keeps it going, an always-on room where members ask who is using which tool, what to recommend, whether anyone is nearby, and what everyone is doing on a Friday night.

What members trade there is not small talk. It is operational, and it works because the usual pecking order falls away. "We are all peers," she says, "there to support each other." One will introduce another to someone who has solved a pricing problem. Another will vouch for a service partner across the country. An MSP with local technicians will handle an on-site job for a peer too far away to make the drive. Carrie describes a recent coaching call with a less experienced MSP stuck on pricing. She sent one email, connected them to someone more established who, in her words, pulled the curtain back and showed them exactly how they did it, then pointed them toward a white-label option so they did not have to build it all themselves. "Within a community, we have so many extensions of ourselves," she says.

She keeps coming back to the same line. "Why struggle alone?"

Leadership is another form of community

If community comes down to who is in the room, Carrie pays as much attention to who is not. She graduated as one of two women in her class, and her first IT teams had barely more. The divide became real to her at a conference years ago, in the line for the bathroom of all places, where the women's line barely existed. She still counts. At every event she looks around and tallies how many women are present. "There's more technical women coming in," she says, "but there's so much more work to be done."

Her advice to women coming up is direct. Some hold back when the loud voices own the table. Carrie's answer is to stop waiting for a seat. "If there's a table you want to be at, and there's no seats, grab a chair and bring your own," she says. "A lot of times we wait for somebody to invite us." Bring the chair, she says, and more often than not you will be welcomed in.

She has no patience for framing this as women against men. It "drives me up the wall," she says, even as she insists the conversation has to happen while the field is uneven. "We have a lot to teach," she says, "just as much as we have to learn." Gender, in her view, should not decide how someone thinks or how they are seen in a room. It still does. That is the hurdle.

Underneath her idea of leadership is a sense of debt. Someone took her under their wing early, made introductions, and drew her in. What she found was simple. "There are so many people out there who are willing to give," she says, "just as much as I want to give." She pays it forward now on a larger stage. A year ago she joined the board of GTIA (Global Technology Industry Association), the global, vendor-neutral industry association, a seat she never expected. In her head it was the top of the top. She went in, she says, as "just a little MSP" who happens to have "a big voice," and that was the point. The room had helped her, so she works to keep it open for the next person.

Find a community

Technology will keep changing. AI will keep getting better. The tools MSPs lean on today will give way to others. Underneath all of it sits something steadier. People still learn best from people, and the most useful playbooks still get passed across a table, in a Discord thread, or in a hallway after a session.

That is what Carrie wants people to take from her story, and it is where she ended the interview. Find a community. Whether it is the CanIT Collective, GTIA, or somewhere else entirely, find one or two or ten. "We aren't alone," she says. Entrepreneurs feel like they are, building their businesses by themselves at midnight. They do not have to. "You don't have to do it alone."