I recently had the pleasure of joining Ed Collupy, principal at Collupy Systems Solutions, LLC and CTVG advisor and facilitator, on Behind the Counter, a podcast presented by Kitestring Technical Services and recorded live at the NRF Show. Vicente Yañez, host and senior system engineer at Kitestring Technical Services, welcomed us for a candid conversation about what is actually holding retailers back from meaningful technology progress.
The result was a refreshingly grounded discussion that the biggest challenge in retail technology right now is not AI or cybersecurity, it is integration.
The Number One Need: Integration
Following VGN’s November Global Summit, Ed surveyed CTVG members to identify their top priorities heading into 2026. The answer was unambiguous: improved integration, meaning getting the platforms retailers already have to work together efficiently and simply at the store level.
As I put it during our conversation, the goal is not for every vendor to do everything. The goal is for each solution to play to its strengths and connect seamlessly with the rest of the ecosystem. That sounds straightforward, but the reality inside most retail operations is far messier.

The "Messy Middle" and the Myth of the Big Bang Rollout
One of the most useful concepts to emerge from the episode was what Vicente calls “the messy middle,” the transition period when a retailer is running old and new systems simultaneously, managing manual workarounds, and trying not to break financials, operations, or supply chain in the process. It is the gap between where you are and where you want to be, and it is where most technology initiatives quietly struggle.
Ed and I both pushed back on the idea that transformation happens in one sweeping move. The more realistic and more sustainable approach is what I called “incrementality,” or building toward a strategic vision in deliberate, quality-driven steps rather than betting everything on a single platform for a decade. Retailers who are already deep in a POS implementation, Ed noted, are often already thinking about what comes next, and that forward-looking mindset is exactly the right one.
The old model of a 10-to-12-year ROI commitment to a single system is giving way to something more agile, where the question is not just whether a solution works today, but whether it gives the organization the flexibility to keep moving forward.
The Human Factor Is Non-Negotiable
The conversation kept returning to a point that is easy to overlook in a technology-heavy discussion, which is that none of this works without people. Ed was direct about it, noting that technology exists to help humans perform better, not to replace human judgment. When AI tools or new platforms are deployed without adequate governance, critical thinking, or frontline input, the results tend to disappoint.
Ed and I both stressed the importance of cross-functional buy-in. The best technology implementations we have seen are ones where IT leaders invite peers from marketing, operations, and even store-level staff into the planning process early, not just for feedback, but because execution is dramatically easier when everyone understands what is in it for them. The flip side matters too. Headquarters teams need to spend time in the store, seeing how technology actually performs when a real customer is standing at the register.
A Word on AI Governance
While Ed and I agreed that AI is far more than a buzzword, we were equally clear that handing the wheel over to any AI system without oversight is a mistake. As AI models become smaller and more capable of running at the edge, meaning directly at the store level, the questions around data governance, PII, PCI compliance, and security become more urgent, not less. The organizations that will navigate this well are the ones with experienced technology leaders who understand both the opportunity and the exposure.
Be sure to watch the entire episode to catch the full conversation.
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