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.

On recent lessons learned: During the pandemic, we weren’t deemed an essential service so the government shut all our stores. That meant all traffic, from a retail perspective, went online. We were doing about 5,000 orders a day and we got flooded well beyond anything we could possibly imagine in terms of what we had built the system for, going up to about 120,000 orders a day. If you’re doing 100kpm and want to do 120, just step on gas pedal a little harder. But we’re talking a 2,400% increase. That’s going 2,400kpm, so pushing the gas pedal harder doesn’t get you there. You need a brand-new engine, new tires, new drivers. And it’s not just fixing the car. You have to fix the roads, change the traffic lights. There are so many things that have to be changed and we had to do thousands every week to figure out how to unlock the scale of the problem we had. It was extremely difficult to do. I also felt personally responsible for putting the corporation in such a challenging position where revenues weren’t coming into the organization.

On appreciating limited resources: When I was at Research in Motion, now BlackBerry, whatever you wanted to spend, whoever you wanted to hire, whatever you wanted to buy, you could do it back then. Whatever you needed. I learned a lot being on the inside about the problems of having too much money and not enough governance and control. And when you have unlimited resources, like I did, you’re able to just do stuff. But constraints actually force you to do things differently and force you to think there’s a better, smarter way. When you don’t have those constraints, you tend to make decisions which are fast and easy as opposed to really innovative and creative.

On digital transformation: The definition back then was to implement e-commerce. It’s funny because there was this perception that e-commerce was just a piece of software or something to implement, when really it’s a radical business transformation. Every aspect of your business changes everything as you start to go down that path. So that led to a variety of things. It gave me the chance to do more, and eventually I was given the opportunity to take on the role I have now for everything we do.

On cybersecurity: Cybersecurity is a business issue, a business imperative. And that helps set the tone. What we’ve done is embed objectives across all of the C levels. When we say it’s everyone’s problem, it’s put in everyone’s objectives and it makes sense. From a business perspective, so many cybersecurity programs focus on tasks, metrics, and maturity models that are hard to get people to care about. But when you start to explain it in business terms around residual risk and cyber risk scenarios, that is our North Star. Whatever plan I have, though, if I’m still doing the same one next year, then I’ve failed because I haven’t adapted because things don’t stand still for an entire year in the world of cyber. So agility and agile operating models, and a focus on business risk scenarios, residual risk, and the ability to pivot, are all really important. The mindset, not only across my peers, but also within technology, within the cyber team, has to change as well. There was a time when if you asked people in the cybersecurity team what their job was, they would’ve said to secure the company and make sure things are safe. But that’s not completely their job. It’s actually to help the business in a secure way. Because the first definition could propagate certain behaviors that aren’t consistent with what we need to do as an organization. Shutting down e-commerce would make us a lot safer but that doesn’t help the business.