Rachel Calhoun – Global VP, Retail, Consumer and Airlines, Kyndryl: Turning AI Investment into Business Outcomes
with Rachel Calhoun, Kyndryl
Rachel Calhoun joined the podcast live from NRF in New York to discuss Kyndryl’s evolution following its spin off from IBM and its growing role in helping retailers deliver tangible business outcomes through technology. As the former managed services arm of IBM, Kyndryl has long been trusted to run mission critical systems that underpin transactions and customer engagement.
Rachel explained how that foundation has expanded into advisory and consulting services, supporting retailers across the full transformation journey. This includes customer journey design, KPI definition, organisational change management, enterprise architecture and implementation, while still maintaining the resilience and reliability of core systems.
A key theme was the challenge retailers face in converting AI pilots into production ready use cases. Rachel highlighted how fragmented systems, siloed data and legacy integrations often hold organisations back. She introduced the concept of the adaptation gap, where consumer expectations move faster than retailers’ ability to integrate new technologies into their back-end systems.
At NRF, Kyndryl’s focus is on retail and on building propositions that leverage agentic AI to improve both customer and employee journeys. Rachel emphasised Kyndryl’s approach of deploying forward deployed engineers to demonstrate value quickly, whether on site with clients or through innovation centres, with the goal of delivering ROI faster through deep integration with mission critical systems.
Jayson Tipp – Chief Development Officer, Playa Bowls: Scaling Retail Technology for Rapid Growth
with Jayson Tipp, Playa Bowls
Jayson Tipp shared an honest account of the technology challenges faced by Playa Bowls as it scales rapidly towards 500 locations. With the brand growing from its entrepreneurial roots, Jayson explained how legacy systems, particularly the POS platform, have struggled to keep pace with expansion.
He described the limitations of operating hundreds of separate POS instances, resulting in fragmented data, complex reporting processes and inconsistent product management across franchise locations. These challenges have created operational friction and slowed the business at a time of accelerated growth.
Jayson outlined the journey towards a new technology ecosystem, including a lengthy RFP process and the complexity of integrating systems without disrupting day to day operations. He stressed that large scale transformations are rarely a simple switch off and switch on, particularly when physical hardware must be replaced in stores.
Change management emerged as a critical theme, illustrated through the introduction of kitchen display systems. While initial anxiety existed among store teams, real world testing quickly demonstrated the benefits, turning sceptics into advocates. Looking ahead, Jayson shared his perspective on AI as a tool to reduce workload and accelerate decision making, particularly in areas such as inventory management and labour scheduling.
Ashley Kechter – Global President, Vuori: Evolving the DTC Model Through Omnichannel Growth
with Ashley Kechter, Vuori
Ashley Kechter joined the conversation following her NRF session on lessons from DTC trailblazers, reflecting on Vuori’s journey since launching as a direct to consumer brand in 2015. Drawing on her experience at Gap, Fabletics and Banana Republic, Ashley shared why Vuori represented a compelling next chapter in her career.
She discussed how the definition of DTC has evolved over the past decade, with physical retail and omnichannel experiences now playing a central role alongside digital. Ashley highlighted the increasing complexity of marketing, where success is no longer driven purely by scale and reach, but by relevance, storytelling and authentic brand connection.
Ashley outlined Vuori’s measured approach to store expansion, focusing on finding the right locations, understanding existing customer demand and ensuring strong brand adjacencies. International growth presents additional challenges, particularly around brand awareness and localisation, but Vuori has seen strong early success by aligning product relevance with targeted marketing.
On AI, Ashley explained that Vuori is using the technology primarily to create efficiency and speed for teams, particularly in paid media and customer service. Rather than replacing creativity or strategy, AI is freeing up time for deeper thinking around markets, product and brand storytelling.
Matt Ezyk – Head of E commerce Technology, Hanna Andersson: Building for Performance and Flexibility
with Matt Ezyk, Hanna Andersson
Matt Ezyk, recently named one of the NRF 2026 Retail Voices, discussed the modern e commerce platform he has helped build at Hanna Andersson. Using a composable architecture with Salesforce on the back end and a modular front end, the business has adopted a flexible, API first approach more commonly seen in much larger retailers.
Matt explained how the strangler pattern methodology allows individual components to be launched incrementally, rather than through a single high risk replatforming. This approach has enabled the team to prioritise areas that deliver the greatest impact, such as checkout and product pages, while remaining adaptable to future innovation.
Performance and speed were central to the discussion. Matt emphasised that no technology investment can compensate for a slow site, particularly on mobile, and shared the team’s focus on achieving sub three second load times.
When it comes to AI, Matt outlined a cautious and pragmatic strategy. Hanna Andersson is primarily enabling AI features within existing vendor platforms, focusing on workflow efficiency, chatbots and product recommendations. He stressed the importance of careful testing and statistical validation, noting that while many retailers feel behind on AI, thoughtful experimentation is more valuable than rushing to adopt every new tool.
Julie Bornstein – Founder and CEO, Daydream: Reinventing Fashion Search and Discovery
with Julie Bornstein, Daydream
Julie Bornstein shared insights from her journey founding The Yes and later launching Daydream, a fashion discovery platform built around natural language search. She explained how earlier AI and machine learning models lacked the ability to understand nuanced consumer intent, limiting how people searched for fashion online.
The emergence of large language models marked a turning point, enabling consumers to describe what they want in natural, expressive language. Julie outlined how Daydream uses AI to understand complex queries, product catalogues, user preferences and even images, allowing shoppers to find relevant items across brands and retailers.
Search and discovery were positioned as the biggest unsolved problems in fashion, given the nuance of fit, style, occasion and personal taste. Julie described how millions of real user queries now inform product development and future problem solving.
Drawing on her experience in both start-ups and large retailers, Julie discussed the challenge of building brand awareness alongside complex technology. Looking ahead, she predicted significant change in how consumers shop for fashion, driven by AI powered discovery. Her advice to retailers was clear: invest in high quality product photography and detailed product copy, as this benefits both customers and AI systems.
Naresh Krishnamurthy – Senior Manager, Business Transformation, KAO UK: AI, Peak Trading and Operational Discipline
with Naresh Krisnamurthy, KAO UK
Naresh Krishnamurthy joined the podcast following his NRF session on redefining peak trading periods such as Black Friday with AI. He challenged the assumption that AI can compensate for weak fundamentals, warning that peak periods stress test forecasting, inventory, fulfilment and service models.
Naresh explained that AI’s greatest impact is often in preparation rather than execution, enabling earlier planning, clearer priorities and more realistic expectations. By sharpening demand signals and highlighting risks in advance, AI helps teams feel more in control and less reactive during high pressure trading periods.
Operational alignment emerged as a major theme, with AI supporting better coordination between marketing, stock availability and fulfilment. For premium brands, this reduces the risk of overpromising and under delivering, protecting both customer experience and brand trust.
Looking to the future, Naresh described AI’s role as a copilot rather than an autonomous decision maker. In an increasingly complex retail landscape, AI will support real time monitoring and decision support within clear boundaries, while humans retain control over judgement, trade-offs and strategic direction.
