How Canadian Tire CIO & CTO balances lessons learned and leading with purpose

Having celebrated its 100th anniversary last year, Canadian Tire has had to perform some deft manoeuvring in the last couple of years to become more agile. And with his dual titles at the company—CIO and CTO—Rex Lee is in the driver’s seat to support digital transformation and implement shared knowledge across teams and management. No small feat considering he’s responsible for a bursting portfolio that covers a family of companies including Canadian Tire retail, Sport Check, Mark’s, Party City, Pro Hockey Life, and several others.

“I moved from telco to tech, high tech to retail, but didn’t think I’d make that jump, nor thought retail would be invigorating,” he says. “But I was wrong. It’s so exciting. I didn’t realize how embedded technology was in everything in retail. And holding more than one role is a bit of a trend right now. The idea being that technology, whether it’s internal or customer facing, has certain constructs that can be applied more broadly. And if you’re able to unify these things, you can harness the power of economies, longer-term thinking, and greater scalability. So my role isn’t just operations and how things work today, but also what’s next and how do we evolve.”

And naturally with a 100-year-old organization come systems that sometimes aren’t entirely modern. As a result, especially during the pandemic, the complexity of legacy infrastructure held back an ability to achieve new things. Finding a way to evolve through traditional IT was essential, and solutions mostly emerged through available talent.

“It’s amazing what happens when you empower people and trust them,” he says. “We didn’t have to compete with priorities of getting money into the company to keep it running. There was no real IT in business. It was all one team working together toward the same goals. I felt so supported by my peers. Sometimes technology gets blamed for things, but everybody realized that it was the situation. Because we were already down this journey, it helped accelerate the move toward an agile operating model where you combine business and technology teams under a single structure. You need the tone at the top and you need to have that opportunity to be able to bring things together. Without that, it’s really hard to create alignment and communicate.”

CIO Leadership Live Canada’s Rennick recently spoke with Lee about his nonlinear career path, the synergy of digital transformation and retail, and the digital overhaul to the business through, and after, the pandemic. Watch the full video below for more insights.

On following the rules: I started my career at Bell Canada and one of the things I learned there was breaking the rules. I sometimes asked folks when it’s appropriate to break a rule when the rule doesn’t actually achieve what it was intended to achieve. It forces you to rethink the rule and what you’re doing. When I started at Bell, I was in this row of cubicles and at the end was a big pile of old PCs, and I took it upon myself to build a server out of them. I then networked it and created shared capabilities, which we didn’t have readily available back then. It was great for information and document sharing, collaboration, and those kind of things, but I got in a little trouble because I wasn’t supposed to take apart equipment and hook it into the network and create privileged access. But it got me noticed in some positive ways, as well as got me thinking outside the box of what my day-to-day job was, saying there’s a better way of doing this.