Hello Reader,

December may be cold, but retail tech is still heating up. This month’s newsletter covers everything from smart POS terminals and AI-driven security to payments modernization, conversational commerce, and the rise of same-day delivery. Plus, we break down the shifts worth paying attention to and the ones that should probably already be on your roadmap.

Target Pushes Conversational Commerce into the Mainstream

Target’s new ChatGPT-powered shopping experience marks a major moment for conversational commerce. Instead of browsing through menus or filters, customers can describe what they need and receive curated options in real time. This signals a shift toward more natural, guided digital shopping that meets consumers where they already are.

Expert POV: Once Target links ChatGPT shopping with Target Circle accounts, personalized offers, and delivery options, this becomes a full funnel commerce experience that reshapes how customers search and shop. The implications for retailers are significant. Conversational AI will not stand alone. It will require clean data, strong integration patterns, and modern architectures that can surface the right information instantly. The retailers that invest early in the right platforms will be the ones positioned to win as conversational commerce scales.

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Six Ways AI Is Rewriting Retail Security

This piece highlights how AI is reshaping loss prevention, drawing on insights from the NACS Loss Prevention and Safety Symposium. It walks through six areas where AI-powered tools, from real-time alerting to advanced surveillance, are changing how retailers detect, prevent, and respond to shrink. The article makes it clear that AI is enabling smarter and faster loss prevention strategies that are now accessible to retailers of all sizes, not just enterprise players.

Kitestring’s Perspective: There are some major inflection points happening in retail security right now. Computer vision continues to make progress, and its future applications look incredibly powerful. Real-time alerting has become table stakes, and the newer, more complete architectures are a step change from the systems we used to cobble together. Biometrics have finally hit the point where lower authentication costs, stronger privacy protections, and solution maturity make them viable in a way they never were before. And with quantum computing looming, payments and POS sit squarely in the blast radius which means every security team needs a plan and a roadmap now, not later.

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Is Your POS Smarter Than a 5th Grader?

The shift from fixed registers to smart, connected POS terminals is accelerating across many retail segments, especially restaurants. This article covers everything from core benefits to must-have features and even addresses the fears associated with transitioning to a new POS. These smart POS terminals unify payments, ordering, loyalty, and real-time data, all while flexing between staffed and self-guided configurations. The result is faster service, less friction, and hardware that finally supports the way customers actually shop.

Expert Take: This trend extends far beyond foodservice. Retailers everywhere are trading traditional registers for modular, intelligent hardware that supports modern payment methods and delivers operational insights without piling on extra systems. Smart terminals speed up checkout, streamline service, and future-proof stores as expectations climb. For retailers planning refresh cycles, this shift is no longer optional. It is quickly becoming table stakes for 2026 and beyond.

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On-Demand Delivery Keeps Expanding Its Retail Footprint

This article reports on a wave of new on-demand delivery partnerships this month as Pacsun, Camping World, and Lush expand their same-day offerings through Uber. Each retailer is testing different use cases from rapid delivery of fashion and beauty products to faster fulfillment of outdoor gear and RV essentials. The piece highlights how retailers are using delivery tactics to meet rising customer expectations around speed and convenience.

Our View: For years, same-day delivery and third-party delivery (3PD) integrations were mostly limited to restaurants and grocery, but that barrier has officially fallen. Non-essential retailers are now jumping into the same-day world and the tech stakes are rising fast. To compete and scale with 3PD partners, retailers need modern POS architectures that can integrate cleanly, push accurate inventory in real time, and handle the operational flow without breaking.

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Watch Out, Denzel: Retail Has a New Equalizer

Lightspeed Commerce’s CEO breaks down the fundamentals that modern stores must get right, from execution to inventory to the systems that tie it all together. The message is clear. Technology has become the equalizer that allows any retailer to compete at scale regardless of footprint or budget.

Kitestring’s Opinion: The biggest takeaway is how much tech has leveled the playing field. Analytics, seasonal insights, and predictive stock once lived exclusively behind Big Retail walls, but today every retailer can tap into a broad ecosystem of service providers with capabilities that often surpass what private setups can support. Integration remains the name of the game, and it is ultimately what turns these tools into the great retail equalizer.

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Payments Are No Longer Plumbing

This article highlights how payments modernization has become an urgent priority, with most retailers and financial institutions (FIs) already in motion or planning to start within the next few months. Customer expectations, competitive pressure, and aging systems are driving major investments, and both groups are committing meaningful budgets and teams to get it done. The takeaway is clear. Modernizing payments promises better customer experiences, faster processing, and long-term savings, but retailers and FIs still worry about cost, disruption, and the complexity of integrating new platforms across existing systems.

Our Take: Payments used to be treated like store plumbing, necessary but not strategic. The latest KPMG insights reinforce how retailers are being pushed to rethink payment systems, in order to stay relevant and competitive. The real question for 2026 isn’t “Which POS should we buy?” It’s “What platform will power the next decade of our omnichannel strategy?”

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Thanks for Reading!

As we wrap up the year, one thing stands out. Retail is shifting faster than the tech stacks holding it up. Payments are evolving, security is getting smarter, and new channels like conversational commerce and same-day delivery are forcing real architectural decisions. If you are planning or prioritizing for 2026, these trends point to the same truth. The future will belong to retailers whose core systems can keep up with their ideas.

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