How Retailers Win in an AI Driven Decade
with Rachel Calhoun, Kyndryl
The episode opens with the return of Rachel Calhoun, Global Vice President for Retail, Consumer and Airlines at Kyndryl, who reflects on how retailers can position themselves for success over the next decade.
Building on previous discussions around AI and Agentic AI, Rachel introduces the concept of a living operating model. Rather than treating transformation as a one off initiative, she explains that retailers must prioritise customer and employee journeys end to end, aligning strategy, technology and execution to deliver continuous value.
Rachel emphasises the importance of integrating AI driven insights into mission critical systems so that they translate into timely, actionable outcomes for the business. Success depends on moving beyond pilots and designing operating models that can evolve as customer expectations and business needs change. Partnerships play a critical role in enabling this, particularly when it comes to integration, organisational change and modernising legacy systems to support future AI capabilities.
Governance is highlighted as a key enabler of continuous transformation. Rachel points to the need for agile, decentralised and cross functional teams that bring together operations, IT and business leaders. By focusing on short, high impact customer journeys that deliver measurable return on investment, retailers can move faster, demonstrate value and build momentum for broader transformation.
Building Trust and Differentiation Through Private Brands at CVS
with Mike Wier, CVS Health
Mike Weir, Vice President of CVS Store Brands at CVS Health, shares insights from his session on the power of private brands.
He begins by outlining the scale and mission driven nature of CVS, serving customers through over 9,000 stores with a strong focus on convenience, healthcare and everyday needs.
Mike explains how CVS approaches private brands with the same rigour as national brands, ensuring quality, simplicity and a strong customer experience across the portfolio.
A recent refresh of health and wellness packaging was driven by the desire to better reflect product quality on shelf, modernise the brand and improve visibility during quick shopping trips. Simplification was a guiding principle, reducing unnecessary wording and making products easier to find and choose.
Innovation remains a priority, with initiatives such as the Well Market food brand and the seasonal Joyward range helping CVS stay relevant and differentiated. Looking ahead, Mike discusses extending trusted CVS brands beyond traditional stores into locations such as airports, reinforcing accessibility wherever customers need them.
AI Enhancing the Beauty Customer Journey at Sephora
with Nadine Graham, Sephora
The conversation then turns to AI and the path to purchase in beauty with Nadine Graham, Senior Vice President and General Manager of Ecommerce at Sephora.
Nadine reflects on how AI is reshaping every stage of the consumer journey, from discovery through to conversion, with a shared industry commitment to making experiences more seamless, relevant and frictionless.
She outlines several AI powered initiatives at Sephora, including in store skin scanning technology and the Smart Skin Scan feature in the Sephora app.
These tools analyse customer skin concerns and deliver personalised product recommendations that can be saved and revisited. Nadine also highlights Sephora’s AI Beauty Chat, a generative AI chatbot designed to support product discovery online. The tool has driven strong engagement, higher conversion and increased basket sizes.
While Sephora continues to explore emerging AI capabilities, Nadine stresses that innovation must always be guided by consumer value. AI is seen as a way to enhance the experience without losing the human touch that defines the brand.
Laying the Foundations for Enterprise AI at Strandbags
with John Khoury, CTO, Strandbags
John Khoury, Chief Technology Officer of Strandbags, shares a candid view of the challenges involved in preparing a retail organisation for enterprise wide AI adoption.
He explains how years of investment in customer facing technology created technical debt at the back end, prompting a major transformation of ERP, data and point of sale systems.
Strandbags is addressing these challenges through parallel initiatives, modernising its ERP with Microsoft Dynamics, building a mature data platform and replacing its point of sale technology, while still experimenting with AI use cases that deliver quick returns.
John highlights the importance of flexibility, allowing the business to adapt as technology evolves.
Employee adoption is a key focus, with Strandbags encouraging teams to experiment with approved AI tools under clear governance. Looking ahead, John outlines how AI agents could transform online commerce, logistics, workforce planning and decision making, provided the right data and technology foundations are in place.
Community First Retail at Barnes and Noble
with Shannon DeVito, Barnes & Noble Inc.
Shannon DeVito, Senior Director of Books at Barnes and Noble, discusses how a community first strategy has reshaped the retailer’s approach. She describes bookstores as a third space, curated by passionate booksellers who understand their local communities and create unique in store experiences.
Shannon explains how empowering booksellers to curate assortments and make recommendations has been central to the company’s turnaround.
Rather than rigid planograms, flexibility and education now guide how stores operate, enabling them to reflect local interests and trends. Collaboration between stores is supported through cluster structures, digital tools and regular knowledge sharing.
While platforms such as BookTok have helped drive renewed interest in reading, Shannon is clear that algorithms should not replace human recommendation.
AI has a role in logistics, customer service and operational efficiency, but the heart of a great bookstore remains its people and their passion for books.
Reducing Checkout Abandonment Through Trust and Payments Innovation
with Dan Coates, ACI Worldwide
The episode concludes with Dan Coates, Director of Product Management at ACI Worldwide, who explores one of retail’s biggest growth leaks: checkout abandonment.
Drawing on research conducted with Paze, Dan reveals the scale of revenue lost at the final stage of the transaction, often driven by lack of trust and friction during checkout.
He explains how trusted payment methods aligned with consumers’ banks can reduce friction by eliminating the need for manual data entry and increasing confidence at the point of payment.
Mobile commerce is highlighted as a particular challenge, where low friction makes it easy for shoppers to abandon and switch retailers.
Looking ahead, Dan discusses the rise of agentic commerce and the importance of secure, tokenised payment solutions that allow AI agents to transact safely on behalf of consumers. For retailers, being visible and trusted within these emerging ecosystems will be critical.
Key Takeaways
Across all conversations, a consistent message emerges. Retail success in the years ahead will depend on strong foundations, clear business alignment and a relentless focus on customer value. AI is moving rapidly from experimentation to execution, but its impact is greatest when paired with modern systems, empowered teams and trusted partnerships.
This episode offers a practical and grounded view of how leading retailers are navigating transformation across technology, brand, community and commerce, providing valuable insights into what it truly takes to win in the next decade.
