Retail Insider and the University of Toronto’s Rotman School of Management brought together four Canadian retail leaders on November 3 for an evening of discussions examining customer loyalty, brand development and the evolving role of physical stores. Held at Desautels Hall in downtown Toronto, the event explored how retailers are responding to consumer expectations while maintaining their identities and pursuing growth.
Titled Finding Customer Fit, the program featured Ian Rosen, president and chief operating officer of Harry Rosen; Meghan Roach, former president and CEO of Roots; Ana Mihaljevic, president and CEO of SMYTHE; and Kaelen Haworth, founder of Toronto fashion retailer Absolutely Fabrics. The speakers shared perspectives on customer relationships, retail investment and brand positioning through individual on-stage conversations.
The gathering marked the second Retail Insider × Rotman event, following an inaugural program on April 15, 2026. Retail executives, entrepreneurs and industry professionals attended the discussions and a networking reception that followed.
Bringing Canadian Retail Leaders Together
Brett Hendrie, Rotman’s director of strategic events, opened the evening by discussing what motivates consumers to choose particular brands, make purchases and return to retailers. His remarks introduced the central theme of understanding customers and the decisions that influence their loyalty.
Retail Insider founder and publisher Craig Patterson moderated conversations with Rosen and Haworth, while Jared Gordon, founder and managing partner of Faculty of Change, interviewed Roach. Sam Maglio, a professor of marketing and psychology at the University of Toronto with a cross-appointment at Rotman, led the discussion with Mihaljevic.
The program was developed through a collaboration involving Retail Insider, Rotman and Faculty of Change, bringing together retail leadership and academic perspectives on the Canadian industry.
Harry Rosen Invests in Stores Worth Visiting
Ian Rosen opened the executive discussions by examining Harry Rosen’s investment in physical retail and its approach to customer service. The Canadian menswear retailer has been updating its store network, including its new 38,000-square-foot flagship at 153 Cumberland Street in Toronto’s Yorkville neighbourhood.
Rosen explained that customers already have numerous ways to purchase merchandise, making the experience of visiting a store increasingly important. He said the retailer wants its locations to be “worth visiting,” with hospitality, personalized service and opportunities for customers to spend time in stores forming part of that strategy.
The Cumberland Street flagship incorporates private shopping areas, event spaces and hospitality amenities designed to accommodate different customer needs. Rosen discussed how these features support personal appointments and create opportunities to build relationships beyond individual transactions.
“We don’t get to establish the expectations of our client,” Rosen told attendees, noting that customers compare retail experiences with the convenience and service they encounter across other businesses.
Rosen also discussed Harry Rosen’s location at Oakridge Park in Vancouver and plans to continue renovating its existing stores. The company expects to update its remaining mainline locations over approximately the next four to five years, extending its approach to store design and customer experience across the network.
Meghan Roach Reflects on Roots’ Brand Evolution
Meghan Roach, who recently stepped down as president and CEO of Roots following the retailer’s ownership transition, discussed the challenges of managing an established Canadian brand with strong customer recognition.
In conversation with Jared Gordon, Roach explained how consumer research helped Roots understand perceptions of its identity and informed decisions about products, pricing and brand positioning.
“I think you have to go directly to the customer and ask them honestly what they believe about the brand,” Roach said, describing the importance of listening to consumers before introducing changes.
Roach also discussed efforts to reduce the retailer’s reliance on discounting. She said Roots had approximately 216 days of storewide sales annually when she began leading the company, prompting management to reconsider how frequent promotions affected customer expectations and the perceived value of its merchandise.
Her comments illustrated the commercial challenges involved in updating a familiar retail brand while maintaining the qualities that originally attracted its customers.
SMYTHE Balances Brand Identity With Expansion
Ana Mihaljevic, recently appointed president and CEO of Canadian womenswear brand SMYTHE, discussed the company’s growth ambitions and the importance of maintaining a recognizable identity as it attracts new customers.
Interviewed by Rotman professor Sam Maglio, Mihaljevic described how the brand serves established customers who regularly add to their wardrobes while reaching new shoppers through digital channels, wholesale partners and physical stores.
She outlined SMYTHE’s internal RED framework, representing the company’s goal of remaining relevant, enduring and distinct. “To be relevant, to be enduring, and to be distinct,” Mihaljevic said, describing the balance between contemporary design and products that retain their appeal over time.
Physical retail is another important component of SMYTHE’s strategy. The company plans to open a boutique at Toronto’s Yorkdale Shopping Centre in early 2027, where customers will be able to experience products directly and receive personalized advice about fit and styling.
Mihaljevic also discussed expectations for further expansion, including a first store outside Canada within the next year. She emphasized that improving the customer experience will be essential as the company grows its physical and digital operations.
Absolutely Fabrics Builds a Toronto Fashion Destination
Kaelen Haworth, founder of Absolutely Fabrics, closed the executive discussions with a conversation about independent retail, emerging designers and the importance of creating a distinctive shopping destination.
Speaking with Craig Patterson, Haworth discussed the retailer’s new 7,000-square-foot store at 1091 Yonge Street in Toronto’s Summerhill neighbourhood. The location opened in September and complements the company’s original Queen Street West store, bringing its assortment closer to an established customer base in surrounding neighbourhoods.
Absolutely Fabrics combines emerging designers, established fashion labels and archival vintage merchandise, with a focus on products that customers may not find elsewhere. The new store has also introduced menswear, expanding the retailer’s offering while maintaining its emphasis on carefully selected fashion.
“It is a global store in Toronto,” Haworth said, explaining her ambition for Absolutely Fabrics to become a destination recognized by shoppers visiting from other cities and countries.
Haworth said building that recognition will depend on expanding the community around the business and strengthening customer relationships, without necessarily requiring additional physical stores.
Continuing the Conversation Across Canada’s Retail Industry
The four discussions provided different perspectives on how retailers can build customer loyalty, from investing in store environments and improving product value to maintaining a distinct brand identity. While the businesses operate at different scales, each emphasized the importance of understanding customers and creating experiences that encourage lasting relationships.
Jared Gordon concluded the formal program by thanking the speakers, organizers and attendees. The evening continued with a networking reception, providing an opportunity for participants to exchange ideas and connect with others across the Canadian retail sector.
The November 3 gathering built on Retail Insider’s collaboration with Rotman and Faculty of Change to create opportunities for dialogue between retail executives, entrepreneurs, academics and other industry professionals. Retail Insider plans to continue developing events that bring together leaders from across Canada’s retail industry, offering opportunities to share experiences, explore business challenges and build professional connections.
