OFFBounds Retail

Everyone has a loyalty program, but very few brands actually create loyalty. In this episode of OFFBounds, Paula Macaggi sits down with Noah Goldberg from Loblaw Companies Limited to unpack what it really takes to build one of the most widely used programs in the world. As the leader behind PC Optimum, with nearly 16 million members, Noah shares how loyalty operates at scale and why it goes far beyond points and discounts.
The conversation explores the shift from rewarding transactions to rewarding engagement, and how digital behavior has become the foundation of modern loyalty programs. It also dives into the complexity behind creating a simple customer experience, the role of first-party data and retail media, and how AI will change the way customers interact with loyalty in the future.

Most retailers don’t have a technology problem, they have a process problem. In this episode, Paula sits down with Liza Amlani to unpack how the disconnect between corporate strategy and store execution actually shows up on the shop floor. From products stuck in stockrooms to stockouts on core items, they explore why so many retail issues are not caused by a lack of tools, but by the way teams operate in silos across merchandising, design, sourcing, and stores.
The conversation goes deeper into what needs to change. Liza shares why process innovation, especially in the concept to market journey, is far more critical than adding new technology. They discuss how leading brands are rethinking collaboration, shortening time to market, and getting closer to the customer. If you care about improving execution, reducing inefficiencies, and building a retail organization that actually delivers on its strategy, this episode is for you.
Click here for Liza's Book: Material Life

UNTUCKit built its brand around a simple idea: shirts designed to be worn untucked. But behind that simple product is a complex technology operation supporting 80+ stores, multiple e-commerce sites, and a growing global business. In this conversation, Paula Macaggi sits down with Jason Lerman, VP of IT & Systems at UNTUCKit, to unpack what really happens behind the scenes of retail technology. They discuss the evolution from “best-in-breed” platforms to what many retailers now recognize as a “Frankenstein tech stack,” the hidden complexity of system integrations, and why the best technology in retail is often the kind customers never notice.
Jason also shares his perspective on vendor relationships, implementation mistakes, legacy technology debt, and how retail leaders should think about building a modern tech stack today. The conversation explores the role of centralized data, the challenges of managing dozens of technology partners, and how emerging technologies like AI and agentic systems could reshape the future of retail operations.
Learn more about UNTUCKit: https://www.untuckit.com
Follow Jason Lerman on LinkedIn: https://www.linkedin.com/in/jason-lerman/

What happens when you build a retail store in public?
When Sammy Nussdorf launched Meadow Lane, he chose a very different strategy from the traditional retail playbook. Instead of opening quietly and announcing the store once the doors were ready, he documented the entire process online. From signing the lease to designing the space and curating the merchandise, the journey unfolded publicly.
By the time Meadow Lane opened in Tribeca, thousands of people had already followed the story and felt connected to the brand. The result was something unusual for a new retail concept: lines forming at 5am on opening day, without spending money on traditional marketing.
This conversation explores what happens when transparency, storytelling, and community become part of the retail strategy. Sammy shares how building in public helped create anticipation before the store even opened and what this approach might mean for the future of physical retail.

Boll & Branch has built its competitive advantage on something many brands overlook: hospitality. In this conversation, Anna Esrov, VP of Customer Experience & Loyalty, shares how the luxury organic bedding brand turns listening into action, from real-time customer feedback that shapes product development to in-home “Room Service” styling that brings five-star hotel energy directly to customers. We explore how surprise and delight becomes part of the culture, how in-house service teams drive retention, and how AI is used to create efficiency without losing the human touch. This is a masterclass in building loyalty through experience, not just product.