OFFBounds Retail

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.

In this episode of OFFBounds, Paula Macaggi sits down with Emily Ketchen, SVP and CMO of Lenovo’s Intelligent Devices Group and International Markets, to explore what it really takes to modernize marketing inside one of the world’s largest technology companies. From building global centers of excellence and putting insights and first-party data at the core of transformation, to leading what she calls a once-in-30-years opportunity to create the AI PC category, Emily shares how Lenovo is shaping the future of compute, brand, and storytelling across 180 markets. The conversation also dives into measuring real marketing impact, turning global partnerships like Formula One and FIFA into business value, and why curiosity, conviction, and simplicity are essential for leaders navigating constant disruption.

Paula Macaggi sits down in New York with Renée Federico, Head of Marketing at Primark US, to explore how one of Europe’s most iconic retail brands is accelerating its growth across America. From launching Primark’s first US brand campaign to building awareness in a store-led model, Renée shares how physical retail drives loyalty, how pop-ups and brand activations fuel customer acquisition, and why listening is the foundation of great marketing. The conversation also looks ahead to one of the most anticipated retail openings, Primark’s flagship store in Manhattan in 2026, and what it takes to scale a global value fashion brand in one of the world’s most competitive markets.