Shoptalk 2024: Tech Talk in a Retail Agora

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When Tony Spring, CEO of Macy’s energetically (and surprisingly) quotes Jelly Roll, “There’s a reason the windshield is bigger than the rear-view mirror,” you could say it’s a quintessential Shoptalk moment. Foresight is everything. Retail tech is a burgeoning industry offering its often-remarkable solutions to legacy and emerging retail. How to make sense of it is another thing altogether.

The Robin Report has collaborated with Shoptalk from the time it was just an inspired idea in Simran’s and Anil’s Aggarwal minds.  Now eight years later the annual Spring celebration of tech talk continues to bring emerging and frontier solutions together in a dynamic retail agora.

Gen AI

We were in the right place at the right time to get a mind-blowing opportunity to bridge theory to practice by witnessing a real-life use case study for Gen AI. Dan Kraemer, adjunct professor of growth strategy and innovation at Northwestern and his grad students are deep into Gen AI as a foresight research tool to shape the future of retail. His presentation at Shoptalk was a convincing, systematic demonstration of how he is using AI in an exercise to create stores of the future. The premise is: What would a store look like for a Gen Z couple preparing to have a family?

Any ideation group could go to town on this exercise. In Kraemer’s case, through a rigorous matrix of classifications, attributes, and descriptions, Gen AI was put to the test with a disciplined series of prompts. The results were a flood of information about the strategy and operations for this hypothetical store including a description, location, merchandise, interior design, marketing, advertising, and a website. And in a suspended disbelief moment, he introduced us to the customers and how they would shop the store – all woven into a metaverse environment. Maybe Jeff Zuckerberg had it right about meta after all.

Kraemer’s demonstration of the power of AI technology would make even the most skeptical a true believer. And that’s what’s so fascinating about the zeitgeist Shoptalk is able to replicate year after year. The enthusiasm, passion and optimism of this retail tech community can revitalize a tired industry with its outdated toolbox.

The Retail Tech Agora

Sure, to a novice understanding the thousands of startup solutions can be arcane, particularly when presented in engineering talk. There is still a challenge for much of retail tech to speak in a language that is easily comprehensible, particularly since our current language structure doesn’t really include a deep syntax for understanding technology.

Two great examples of entrepreneurs at Shoptalk who are making AI relevant and understandable are Purva Gupta, co-founder of Lily and Terek Müller, co-founder of About You/Scayle. In simple terms, Lily uses AI to create natural language descriptions of products to make the online search for apparel more intuitive, enjoyable, and successful. “I want a dress to wear to my cousin’s wedding in Jackson Hole” synthesized by AI to deliver appropriate choices is a godsend for an otherwise non-contextual online search. In About You/Scayle’s case, emulating the thrill of discovery and impulse purchasing we experience in physical retail now delivered by AI online is why About You has become the second largest digital marketplace in the EU. 

Hope and Discovery

The Robin Report has collaborated with Shoptalk from the time it was just an inspired idea in Simran and Anil Aggarwals’ minds. Now eight years later the annual Spring celebration of tech talk continues to bring emerging and frontier solutions together in a dynamic retail agora. With its successful meet-up program, attendees can have a real conversation with someone who actually wants to meet them and learn about their business needs. It makes being with 10,000 people, personal.

This year’s odyssey with its dramatically staged shooting stars backdrop was an interwoven narrative on how to unlock the potential of unified commerce, everyone’s darling AI in retail, emerging customer journeys, and the power of brands. You could argue that this pretty much covers how the entire retail ecosystem needs to evolve. 

Living Without Borders

Every customer wants a seamless experience to buy where, when, and how she wants from any retailer. Customers don’t care about the channels and silos on the backend; they want to shop from a synchronous, harmonious brand. And not to get all Big Brother about it, demanding shoppers expect the experience to be personal, meaningful, and customized. In a full-scale rethink, systems-thinking and holistic approaches are needed to update the business model. Technology and its applications, data, and integrated systems are the unlock to deliver the transparently frictionless experience customers demand. Simply stated, well-executed unified commerce has become table stakes.

The Matrix

The elephant in everyone’s room is Gen AI and its astonishing speed. The challenge for retailers is how to integrate it into their operations with employee buy-in and customer guardrail. Every shiny new tool always appears to be the silver bullet we’ve been waiting for to shape a better future. Digital transformation comes with its risks, principally the human factor which can be highjacked by resistance, anxiety, lack of understanding or in the case of Gen AI, bias. It’s human beings, not systems, that can derail any tech-infused pathway forward.

AI in its mutable forms is distilled by Shoptalk onto three logical applications: improvement in productivity and efficiency, amplifying the customer experience, and enhancing creativity – preferably all three delivered simultaneously. Ultimately AI needs to solve a real, not imagined problem. Maxim to operate by: Don’t get dazzled or star struck, use common sense.

It’s Only About Me

Every customer odyssey is unique to the shopper, but not for retailers. The delivery of each customer experience is in the throes of disruption from an overly informed consumer, DTC disintermediating brands, and new retail media and marketing campaigns. TRR’s job is to keep it honest, so we just have to say a word about retail media. With the exception of its delivery platform, retail media seems pretty similar to the circulars, catalogs and flyers we grew up with. Nevertheless, marketing messaging today is one-to-one, not one-to-many. That’s a sea change propelled by technology, not the least of which is TikTok viewed as a wildly successful personal marketing and commerce experience. The customer journey is possibly the single most under-siege sector of retail and implodes weekly with new digital models and trendy me-tailing influencers.


Brands are having their own moment. We’ve heard about authenticity and transparency ad nauseum. Origin stories, founder’s narratives, and brand storytelling are the new cultural memes. The foundational core is trust, and there is a lack of it. Surrendering to the customer is a hard nut for a brand, but collaboration and co-creation are not going away any time soon.

Key Tactics

There are so many conversations at Shoptalk, it’s a field day to decide which gems to highlight. Among the many, we have chronicled some topline tactics as a blueprint for forward-thinking retail operations in the short and long term.

  • Market conditions are going to remain disruptive, requiring retailers to be agile and responsive to evolving marketplace dynamics with foresight and future-oriented strategies that can unlock new potential. Central to this is maintaining trust with customers ensuring that a company’s offerings and image reflect the brand’s ethos, achieving effective outcomes.
  • Technology provides the infrastructure to modernize retail operations. Reprioritize capital investment and focus on key areas to enable growth, accountability, and transparency. Take a pause and develop a modern technology vision and transformation roadmap focused on selected key areas. Slow down topline growth temporarily to rebuild foundational technology platforms to enable future growth.
  • Create unified retail media experiences that integrate streaming TV, online video, web, and in-store media and develop metrics to measure each campaign’s performance related to the customer shopping journey.
  • Take a page from Tony Spring’s (more surprising news) education in hotel and restaurant management, and rethink retail through a hospitality lens—prioritizing customer experience, satisfaction, and excitement as core to the business.
  • Embrace the ambiguities of social shopping trends in every category. TikTok is a role model in personalized one-to-one social commerce bolstered by integrating in-app purchasing. Shift your perspective to include curators, influencers, content creators, partners, affiliate marketing and collaborations. Invest in tech to refine the success and popularity of social commerce to maintain a competitive edge.
  • In terms of workplace culture and career development, collaborate, co-create and consult. Create management frameworks allowing employees to innovate outside of day-to-day work. Delegate with trust and hold teams accountable. Offer personal development with e-learning, teachable project assignments, and job rotations. Support inclusion without bias with holistic principles to facilitate a diversity of thought within teams.

Bonus Point: JoMO

So, in the context of Shoptalk, retail tech is a powerful enabler, business builder, and customization tool. But there’s a new kid in town that may be replacing FoMO, which has jet-propelled social media and technology in general. And here’s where the in-store retail experience has an edge, finally.  JoMO is the joy of missing out. Stow your phone, disconnect, and go to a store to have a good time – in person. Retailers can leverage JoMO by offering real-time experiences that make shopping a meaningful discovery experience in an environment that provides inspiration and pleasure. We need more of it.

The outcome of Shoptalk 2024 is to inspire retailers to fuse the science of retail with the art of experience. It’s useful to remember that shoppers are people, not data points. Everyone wants to build good memories. And we want to trust any brand we’re investing in. Shoptalk got that memo and is hosting a new Fall event in Chicago to continue to rejuvenate retail and its relevance. Stay tuned for more.



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