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Interview

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Transforming Canada’s Largest Grocer into a Digital Powerhouse

📍Toronto, Canada

When Lauren Steinberg joined Loblaw Companies Limited, Canada’s largest retailer with more than 2,500 locations, the company’s transactions took place entirely in brick-and-mortar stores. Recognizing the need for change, Loblaw took a bold approach — creating a separate digital division with its own P&L, operating outside the traditional corporate structure. This “startup within the enterprise” mindset allowed the team to move quickly, break conventional rules, and compete for top tech talent, setting the foundation for Loblaw’s digital transformation.

From its first foray into online grocery with a costly pilot store to today’s network of hundreds of streamlined Click & Collect locations, Loblaw’s journey has been one of iteration and agility. The company resisted making massive early investments, instead favoring a test-and-learn approach that kept it responsive to evolving customer needs. Over time, Loblaw shifted from monolithic systems to a composable architecture, enabling rapid adoption of innovations like retail media networks, social commerce, and AI-driven personalization.

Steinberg highlights that personalization has become a cornerstone of Loblaw’s digital strategy. By leveraging data from its massive PC Optimum loyalty program, the company is overcoming one of e-commerce’s biggest hurdles — product discovery. Today, 44% of items added to online carts through personalized recommendations are products customers have never purchased before. Beyond grocery, the company’s digital reach spans beauty, apparel, and pharmacy, with tools like “Swap Canadian” and “Swap and Save” building trust and delivering value during challenging economic times.

While Loblaw’s digital team still operates with a startup mentality, integration with the broader enterprise has brought new advantages, from supply chain expertise to merchandising strength. For Steinberg, the keys to success include surrounding herself with exceptional talent, mastering storytelling to drive buy-in, and seeking opportunities beyond her immediate remit. Her vision extends beyond transactions — using technology to connect food, health, and personalization in ways that enrich the lives of millions of Canadians.

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A key theme behind Coterie’s success is the power of messaging. While many brands focus heavily on channels, Ankur emphasizes that growth begins with clearly communicating the value you create.

Interview

A key theme behind Coterie’s success is the power of messaging. While many brands focus heavily on channels, Ankur emphasizes that growth begins with clearly communicating the value you create.

Coterie: When Product, Brand, and Experience Align

A key theme behind Coterie’s success is the power of messaging. While many brands focus heavily on channels, Ankur emphasizes that growth begins with clearly communicating the value you create.

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Under Ryan Holm's leadership, the 111-year-old jewelry retailer has invested in technology that removes administrative burden while protecting human connection.

Interview

Under Ryan Holm's leadership, the 111-year-old jewelry retailer has invested in technology that removes administrative burden while protecting human connection.

How Helzberg Uses Technology to Remove Frontline Burden

Under Ryan Holm's leadership, the 111-year-old jewelry retailer has invested in technology that removes administrative burden while protecting human connection.

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Interview

Growth has not come from nostalgia alone. Under Satanas’ leadership, HANRO USA invested in modern acquisition channels while playing the long game on brand building. Paid social laid the foundation, but streaming ads delivered a breakthrough moment.

How HANRO US Used Streaming Ads and Clienteling to Accelerate Growth

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At the center of this transformation sits an unusual balance of rigor and creativity. Hoerning often describes it as the tension between data and intuition.

Interview

At the center of this transformation sits an unusual balance of rigor and creativity. Hoerning often describes it as the tension between data and intuition.

Inside Westwing’s Turnaround: The Decisions That Changed Everything

At the center of this transformation sits an unusual balance of rigor and creativity. Hoerning often describes it as the tension between data and intuition.

Trends

The Rise of Brand Memberships and the Future of Customer Loyalty

Brand memberships are having a moment in retail, and it is not a passing one. Across fashion, beauty, grocery, and home, brands are moving beyond traditional loyalty programs built on points and discounts and instead creating paid or value-based memberships that promise access, belonging, and emotional connection.

Brand memberships are having a moment in retail, and it is not a passing one. Across fashion, beauty, grocery, and home, brands are moving beyond traditional loyalty programs built on points and discounts and instead creating paid or value-based memberships that promise access, belonging, and emotional connection.

Trends

Brand memberships are having a moment in retail, and it is not a passing one. Across fashion, beauty, grocery, and home, brands are moving beyond traditional loyalty programs built on points and discounts and instead creating paid or value-based memberships that promise access, belonging, and emotional connection.

The Rise of Brand Memberships and the Future of Customer Loyalty

Brand memberships are having a moment in retail, and it is not a passing one. Across fashion, beauty, grocery, and home, brands are moving beyond traditional loyalty programs built on points and discounts and instead creating paid or value-based memberships that promise access, belonging, and emotional connection.

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