Over the next two weeks, strategy will be revealing the 2025 Marketers of the Year. Check back here every day for profiles on the brand leaders, featuring Skip’s Rachel MacAdam below and others such as OLG’s Maxine Chapman. This article was previously featured in the Winter 2025 issue of Strategy Magazine.

After spending almost 14 years at Air Miles, Rachel MacAdam decided to start a new chapter in her career last year. Leaving the travel industry behind, she joined the Canadian delivery service Skip, taking on the role of VP of marketing in July 2023. Her mission? To bring a fresh perspective to how Skip approaches marketing, customer experience and loyalty.

“I was actually very familiar with Skip through my work at Air Miles,” MacAdam says. “While Air Miles is the connector between brands and customers through that loyalty experience, Skip connects consumers, restaurants and retailers through our courier engagement. That idea of creating consumer value propositions that satisfy the needs of all three stakeholders was there.”

Since joining, MacAdam has made big changes to enhance the customer experience, from personalized digital tools to new partnerships. She also shifted the marketing team’s focus from isolated metrics to a more holistic, data-led approach that supports Skip’s broader business goals.

One of her biggest achievements has been redefining Skip’s identity. In October 2024, the company officially dropped “theDishes” from its name, reflecting its expanded offerings beyond restaurant meals, and added a maple leaf to its branding.

“We were missing out on this huge point of differentiation in that Canadians didn’t know we were a Canadian brand. We were born and raised in the Canadian Prairies, and when you’re in a very transactional category like we are, those points of differentiation matter,” MacAdam says. “When we did research, more than 50% of Canadians said: ‘If I knew Skip was Canadian, I would choose you over others’.”

The rebrand included a major advertising campaign, dubbed “Skip to the Good Part,” by newly appointed agency Courage, and featured American actor Jon Hamm returning as the company’s spokesperson after a five-year hiatus. At the time of its launch, MacAdam told strategy that previous global adaptations with celebs like Katy Perry and Snoop Dogg were deemed not differentiating enough to break through. “When we tested the original Jon Hamm work, versus the global work, we really felt there was an opportunity to point back to our roots, but [also] to the new story of Skip, and the wider offerings we bring to the table.”

The humorous campaign features Hamm inserting himself into conversations and advocating that people “skip” hassle-laden activities like buying heavy bags of kibble and even skipping lengthy business meetings and restaurant lines. With the tagline, “Coulda skipped it? Shoulda skipped it!,” the campaign marked a shift in the brand’s focus from being seen as a food delivery service to a more versatile convenience platform.

“[Skip to the Good Part] is omnichannel and everywhere,” MacAdam says. “By far, it’s one of our largest investments in the history of Skip.”

The rebranding and repositioning efforts paved the way for the most ambitious launch in Skip’s history. In November 2024, MacAdam led the launch of Skip+, a premium membership program that looks to deliver more value to customers. Skip+ offers free delivery, bonus points and reduced service fees, along with perks like discounts and experiences from CIBC, WestJet, Live Nation and the NHL.

“We felt that there was a gap and that was an opportunity for us to own the experiences that we could bring to consumers through our Skip+ membership offering… Hockey and sports are really important, but we also know Canadians are passionate about concerts and live entertainment, and that has certainly seen tremendous growth since COVID,” she notes.

MacAdam’s loyalty expertise has been crucial to Skip+’s success. At Air Miles, she helped build its Collector program to reach 10 million households and generate over $25 million in revenue. She’s now applying that experience to make Skip+ not just functional but rewarding and tailored to Canadians’ interests.

MacAdam is also ensuring Skip stays culturally relevant. When Kendrick Lamar’s diss track targeted Drake and mentioned Toronto’s New Ho King, MacAdam and her team partnered with the restaurant to offer a discount using the code “6GOD.” It was intended to tie the brand into a trending moment while also spotlighting Skip’s local partners.

Continuing to pull on her experience working with brand partners in loyalty, MacAdam led a new partnership with Starbucks in March 2024, highlighting the company’s ability to deliver more than dinner. The partnership drove app traffic and brought more variety to Skip’s menu and, in October 2024, Skip became the exclusive delivery partner for Shake Shack’s debut in Toronto.

Finally, MacAdam spearheaded an NHL partnership, with the “Order, Shoot, Win” contest that let fans win hockey-themed prizes while driving in-app engagement during games. The campaign, which helped link Skip to one of Canada’s favourite pastimes, reinforced the company’s identity as a Canadian brand.

Looking ahead, MacAdam’s focus will be on forging partnerships with brands that complement and enhance Skip’s value proposition, whether they be restaurants or retailers. “Because of my experience at Air Miles and my knowledge of loyalty, we’re able to look at what the current market was offering consumers in terms of subscription and loyalty and see where there are gaps – as well as where the white space is that Skip can leverage to introduce something fundamentally different in our category.”

With files from Chris Lombardo