The mandate facing most loyalty operators right now is to deliver more value while spending less and proving the ROI, and the math does not work on its own.

Canadian consumers have turned to points and rewards as a practical hedge against the cost of everyday life, and their expectations are rising fast. Meanwhile, budgets are declining within the organizations running those programs.

Strategic partnerships are one of the most credible answers to that tension: the multi-year, customer-centric kind that expands what a program can offer without requiring the brand to carry the full cost alone.

In recent interviews, three of Canada’s most active architects of this shift shared what they’ve built, what they’ve learned, and what it actually takes to get these partnerships off the ground. All three will be keynote speakers at The BIG Handshake™ Loyalty Toronto on April 21, 2026.

• Josh Meyer is AVP Loyalty Partnerships at Canadian Tire
• Rachel MacAdam is VP Marketing at Skip
• Steve McClelland is VP Loyalty at WestJet

Why Partnerships, and Why Now

For Rachel MacAdam, partnerships are structural to how Skip+ was designed from the start:

“Partnerships add tremendous value to a loyalty strategy, opening up new reach and audiences you might not otherwise have, and creating a great opportunity for value exchange.”

Josh Meyer frames it as the logical evolution of a program that had grown as far as it could within its own enterprise:

“The next logical step in providing relevance in terms of places to earn and ways to engage customers is going outside of our own enterprise.”

For Steve McClelland, the change is less about importance and more about friction. Linking technology has made it cheaper and faster than ever for customers to connect programs, removing the need for expensive point-of-sale integrations or physical cards:

“Partnerships are just as important as they used to be. What has changed is how they can be leveraged. Linking technology makes it cheaper to get in and deploy at scale.”

Choosing the Right Partner

All three executives are emphatic: not every partnership is the right partnership. Steve McClelland recommends starting with categories before evaluating specific brands. For WestJet, the framework is financial services first, then fuel, grocery, and high-frequency retail, a portfolio that supports the aspirational trip WestJet ultimately sells:

“You look at the categories you’re trying to fill, then ask what partnerships will support the engagement and activity you want. After that, it’s more of a dating game of who’s available and if you’re a good fit.”

Rachel MacAdam describes Skip’s evaluation in terms of brand fit as much as functional value:

“We haven’t partnered with every brand that has come to us. It needs to fit the criteria. We want a curated list that our customers can look at and say, I understand why Skip is partnering with them, and they are bringing something of value to me.”

WestJet, Live Nation, and CIBC each serve a distinct purpose. None of them is there simply because they showed up.

Josh Meyer adds a layer many brands overlook: in Canada’s increasingly interconnected loyalty landscape, you cannot evaluate a prospective partner in isolation:

“You need to consider not only who your prospective partners are, but also who their partners are, and any conflicts or complementary effects that may arise based on their partner networks.”

The Flywheel in Practice

These three programs are not just philosophically aligned; they are directly connected. Skip and Canadian Tire are both active WestJet partners. WestJet points can be earned on Skip orders and redeemed for Skip credits. Triangle Rewards members will soon earn Canadian Tire money through WestJet activity, creating a web of mutual reinforcement that benefits members across all three programs.

What makes the model distinct from a traditional coalition is that brand ownership is preserved on both sides. It is an ‘and’ proposition rather than an ‘or’ proposition, as Josh Meyer puts it:

“We are only giving customers the options to earn more. And that is certainly well received in the current economy.”

Rachel MacAdam describes a similar dynamic at Skip, where the partnership model is explicitly designed to create mutual value for the customer and both brands:

“When you create mutual value for both brands, you’re both committed to building the relationship. In all of our partnerships, there is a mutual desire to innovate and grow.”

What the Numbers Are Showing

Canadian Tire is furthest along with Petro-Canada, now roughly two years in. Customers who engage with that partnership subsequently spend more at Canadian Tire’s retail banners, to the tune of over $100 million to date, compared to lookalike customers who do not. Josh Meyer is careful about the language:

“It has proven our hypothesis. It certainly gives us a lot of confidence as we move forward with our other partners. It did prove causality, not just correlation.”

For Canadian Tire, RBC launched at the end of October with early participation tracking ahead of expectations, and linking, which some have flagged as a friction point, has not proven to be a barrier.

At WestJet, Steve McClelland describes a strong start with both TELUS and Skip:

“We went through our year one linking target on TELUS within two days. We’re also well ahead of schedule with Skip. Canadian consumers are willing to participate when the value is there, and it’s easy and low friction.”

At Skip, CIBC customers acquired through the partnership are proving to be higher value than those from other channels. A well-chosen partner brings an audience with genuine affinity.

The WestJet data at Skip is particularly instructive: when customers redeem WestJet points on Skip, they place another order within two to three days. They are stretching their dollar and coming back for more.

What It Takes to Get There

Josh Meyer identifies internal readiness as the most underappreciated prerequisite, more significant than technology or budget:

“Companies really need to be ready to embrace partnerships as a core pillar of their loyalty and customer strategies. It takes a lot of investment, resources, and organizational alignment. It is not a small feat to bring these off the ground.”

Steve McClelland’s advice: understand your own program deeply before bringing in partners: define your value proposition, your target segments, your strategy. Rachel MacAdam adds a pointed note for brands that assume partnerships are only for large organizations:

“Sometimes it’s better to partner with another brand if you can’t truly drive scale and frequency on your own. Building emotional loyalty is an underrated element of a loyalty value proposition.”

Josh Meyer’s closing reflection captures the spirit of all three perspectives:

“Partnerships are not for the faint of heart. They can be hugely impactful, but it is an organizational muscle you have to build. You get out what you put in. The results, I think, speak for themselves.”

Editor’s Note

Josh Meyer, Rachel MacAdam, and Steve McClelland will be keynote speakers at The BIG Handshake™ Loyalty Toronto, taking place on April 21, 2026, at the Sheraton Centre Toronto. Registration here.