This week on The Remarkable Retail Podcast, Steve Dennis and Michael LeBlanc break down the forces reshaping retail before sitting down live at Shoptalk in Las Vegas with Matt Baer, CEO of Stitch Fix.

The episode opens with a wide-ranging look at the macro pressures bearing down on the industry—geopolitical conflict, rising tariffs, and supply chain strain. Earnings from Nike and RH reveal a consistent theme: even iconic brands can stumble when positioning and innovation lag behind a volatile consumer environment. In grocery, the "collapse of the unremarkable middle" continues as Walmart, Amazon, Aldi, and premium players squeeze traditional operators like Albertsons. A wave of M&A activity—including Allbirds' dramatic valuation collapse, Bed Bath & Beyond's improbable resurrection, and its acquisition of The Container Store—underscores just how much disruption is still unfolding. The hosts also push back on the hype around AI tools like Macy's shopping assistant, cautioning against confusing correlation with causation.

At the center of the episode is a compelling conversation with Matt Baer, who outlines how Stitch Fix is executing a disciplined turnaround built on three phases: establishing a strong operational foundation, reimagining the customer experience, and returning to sustainable growth. Four consecutive quarters of improving revenue trends suggest the strategy is working.

Baer's core argument is that true personalization isn't about volume or targeting—it's about relevance, timing, and understanding customers at a granular level. Stitch Fix achieves this by pairing deep data and AI-driven recommendations with human stylists who bring judgment, empathy, and relationship-building to a category that remains inherently emotional. New tools like AI styling assistants and digital visualization are enhancing that human element, not replacing it.

The episode closes with forward-looking perspective on retail crime, supply chain vulnerability, and macroeconomic uncertainty—and a clear throughline: in an increasingly chaotic landscape, agility and strategic clarity aren't optional.

Join us at the CommerceNext Growth Show in New York June 23rd and 24th with this exclusive discount code for 10% off general admission tickets and FREE retail tickets: Your code is "REMARKABLE" . See you in the Big Apple!

About Us

Steve Dennis is a strategic advisor and keynote speaker focused on growth and innovation, who has also been named one of the world's top retail influencers. He is the bestselling author of two books: Leaders Leap: Transforming Your Company at the Speed of Disruption and Remarkable Retail: How To Win & Keep Customers in the Age of Disruption. Steve regularly shares his insights in his role as a Forbes senior retail contributor and on social media.

Michael LeBlanc is a senior retail advisor, keynote speaker and media entrepreneur. Michael has delivered keynotes, hosted fire-side discussions hosted senior retail executive on-stage in 1:1 interviews worldwide. Michael produces and hosts a network of leading retail trade podcasts, including The Remarkable Retail Podcast, The Voice of Retail The Food Professor, The FEED powered by Loblaw and the Global eCommerce Leaders podcast. He has been recognized by the NRF as a global Top Retail Voice for 2025 and 2025 and continues to be a ReThink Retail Top Retail Expert for the fifth year in a row.

Steve Dennis and Michael LeBlanc are joined by guest co-host Neil Saunders, Managing Director and retail analyst at GlobalData, bringing his signature analytical rigour and on-the-ground store insights to a wide-ranging discussion of the week’s biggest retail developments and the future of AI-powered commerce.

For our feature interview, Steve sits down live at ShopTalk with Bret Taylor, Chairman of OpenAI and CEO and co-founder of Sierra. Taylor outlines how AI agents are emerging as the new “digital front door” for retail, unifying customer interactions into a single intelligent interface.

Bret explains the shift from rule-based automation to agentic systems capable of reasoning and decision-making, enabling retailers to deliver faster, more personalized, and more empathetic experiences. From instant warranty claims to seamless delivery scheduling, AI agents are redefining customer service and turning friction points into loyalty drivers.

The episode opens with a reflection on David Simon's impact on Simon Property Group and mall reinvention. Neil and Steve discuss how Simon proved physical retail can remain productive and relevant when well managed. The conversation then turns to Saks Global’s decision to reverse several planned store closures, with Steve & Neil highlighting the strategic interplay between retailers and landlords.

The group connects this to broader industry dynamics, including the risks of anchor tenant closures and the importance of maintaining mall ecosystem vitality.

A key moment comes as Saunders weighs in on the NRF’s 2026 retail forecast, labelling it “toppy.” The trio challenges the assumptions behind the optimistic outlook, citing cautious retailer guidance, constrained consumer spending, and macroeconomic uncertainty. Saunders’ perspective reinforces a growing disconnect between industry forecasts and operational reality.

The discussion shifts to the intensifying race for ultra-fast delivery, as Amazon, Walmart, and others push one-hour and same-day fulfillment. Saunders provides a grounded view of consumer behavior, noting that while demand for immediacy is growing, the economics remain challenging and uneven across the retail landscape.

Join us at the CommerceNext Growth Show in New York June 23rd and 24th with this exclusive discount code for 10% off general admission tickets and FREE retail tickets: Your code is "REMARKABLE" . See you in the Big Apple!

About Us

Steve Dennis is a strategic advisor and keynote speaker focused on growth and innovation, who has also been named one of the world's top retail influencers. He is the bestselling author of two books: Leaders Leap: Transforming Your Company at the Speed of Disruption and Remarkable Retail: How To Win & Keep Customers in the Age of Disruption. Steve regularly shares his insights in his role as a Forbes senior retail contributor and on social media.

Michael LeBlanc is a senior retail advisor, keynote speaker and media entrepreneur. Michael has delivered keynotes, hosted fire-side discussions hosted senior retail executive on-stage in 1:1 interviews worldwide. Michael produces and hosts a network of leading retail trade podcasts, including The Remarkable Retail Podcast, The Voice of Retail The Food Professor, The FEED powered by Loblaw and the Global eCommerce Leaders podcast. He has been recognized by the NRF as a global Top Retail Voice for 2025 and 2025 and continues to be a ReThink Retail Top Retail Expert for the fifth year in a row.

This week on The Remarkable Retail podcast, Steve Dennis and Michael LeBlanc begin with a sweeping look at the key retail and macro stories of the week, then dive into a compelling interview with Jennifer Woo, Chairman and CEO of Hong Kong-based luxury retailer Lane Crawford.

Woo shares her unusual path into retail leadership, from studying psychology and working in advertising to joining her family’s business and ultimately transforming Lane Crawford into one of the most distinctive luxury department store operators in the world. She explains how Lane Crawford has rethought the traditional department store model by operating compact stores in extremely expensive real estate markets, working with unusually short leases, and maintaining an owned-buying model rather than relying on concessions. That structure gives the company more control over the customer experience and allows it to deliver seamless service across categories.

Woo describes Lane Crawford as relationship-driven rather than transaction-driven, with associates empowered to build client relationships through supportive tools and internal recognition rather than scripts. Her examples of extraordinary service during and after the pandemic illustrate this approach. Woo also details Lane Crawford’s investment in independent designers and a lifestyle-led merchandising strategy. She emphasizes that AI and digital tools should only enhance, not replace, human judgment and connection.

In the opening news segment, Steve and Michael tackle the retail implications of the Iran war, particularly its impact on oil, inflation expectations, interest rates and retailer planning. They discuss the NRF’s somewhat surprisingly upbeat retail sales forecast and break down recent earnings from Macy’s, highlighting Bloomingdale’s strength relative to the core Macy’s banner, and examine Lululemon’s uneven performance, tariff pressures and ongoing boardroom drama. They close the earnings discussion with Five Below, praising its sharp positioning and standout growth in an increasingly crowded value retail space.

The final segments extend the conversation with Steve’s remarkable story of the week on digitally native vertical brands losing momentum, and Michael’s reflections on Gen Z shopping habits, AI anxiety and the limits of assuming young consumers will automatically embrace AI-powered commerce. The episode wraps with radar-screen commentary on U.S. tax refunds, consumer spending and the potential precipitous slowdown in luxury demand in the GCC.

Join us at the CommerceNext Growth Show in New York June 23rd and 24th with this exclusive discount code for 10% off general admission tickets and FREE retail tickets: Your code is "REMARKABLE" . See you in the Big Apple!

About Us

Steve Dennis is a strategic advisor and keynote speaker focused on growth and innovation, who has also been named one of the world's top retail influencers. He is the bestselling author of two books: Leaders Leap: Transforming Your Company at the Speed of Disruption and Remarkable Retail: How To Win & Keep Customers in the Age of Disruption. Steve regularly shares his insights in his role as a Forbes senior retail contributor and on social media.

Michael LeBlanc is a senior retail advisor, keynote speaker and media entrepreneur. Michael has delivered keynotes, hosted fire-side discussions hosted senior retail executive on-stage in 1:1 interviews worldwide. Michael produces and hosts a network of leading retail trade podcasts, including The Remarkable Retail Podcast, The Voice of Retail The Food Professor, The FEED powered by Loblaw and the Global eCommerce Leaders podcast. He has been recognized by the NRF as a global Top Retail Voice for 2025 and 2025 and continues to be a ReThink Retail Top Retail Expert for the fifth year in a row.