Hello Reader,

This month’s Behind the Counter proves retail never sits still. From system downtime that still haunts operators, to Zebra’s billion-dollar bet on hardware ecosystems, to Champs proving omnichannel can actually work, the message is clear: the tech you choose today defines your customer experience tomorrow. Plus, shoppers are prepping their AI sidekicks for Black Friday, while swipe fees are finally getting the side-eye they deserve. Keep reading for the trends and takeaways that you will want in your back pocket before your next strategy meeting.

Winning Loyalty Across Generations

Retailers face the challenge of engaging customers from Gen Z to Boomers, each with different expectations for brand loyalty and shopping experiences. This article explores how brands can cultivate meaningful connections by tailoring strategies to diverse generational values and behaviors.

Expert Take: Any retail strategy today must account for a customer base that spans multiple generations. Marketing and PR may shape the message, but it is your technology that delivers it. If your platform is not built on flexibility and growth, the demand for new capabilities will leave you scrambling. Online and in-store can no longer be treated as separate worlds.

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Prepping for POS Success

Less than half of retailers say their POS supports an innovative store experience, which means too many are running on systems that slow down growth instead of enabling it. A POS upgrade is all about creating room for speed, new capabilities, and unified operations. But modernization takes more than a vendor contract. It requires a clear business case, mapping your architecture, aligning leadership, and preparing store teams to embrace change. This article gives retail leaders a clear playbook for how to prepare for a system upgrade.

Kitestring’s View: POS upgrades are among the toughest projects in retail, and too many fail because they are treated like IT side projects. Success comes when the organization tackles both the technical and cultural shift head-on. Because the point of sale is not just a system, it is the heartbeat of your business.

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Zebra’s $1.3B Bet on Retail Hardware Ecosystems

Zebra’s acquisition of Elo Touch is more than a headline deal. It signals a future where retailers look to one partner for everything from handheld scanners to kiosks to back-of-house tech. This consolidation could simplify vendor management, speed up rollouts, and unlock smarter self-service experiences.

Kitestring’s View: This move shows how quickly retail hardware is shifting from standalone devices to integrated ecosystems. By combining Zebra’s mobility and analytics with Elo’s kiosk expertise, the stage is set for more seamless checkout models, intelligent displays, and rapid adaptation to “scan and go” or vision-based shopping. For retailers, the potential upside is clear: fewer compatibility headaches, faster innovation, and in-store tech that finally feels cohesive.

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Champs Levels Up the Omnichannel Experience

Champs is reimagining its stores with digital touchpoints that blur the line between online and in-store. From window screens mirroring the app to in-store kiosks that connect directly to e-commerce inventory, the goal is one seamless experience, no matter how or where customers shop.

Our Perspective: This is a strong example of omnichannel done right. The tech may look like marketing flash, but behind it is an integrated platform that aligns content, inventory, and customer interaction. The real challenge for most retailers is not putting screens in stores; it is making sure those screens are connected to accurate data and reliable systems. Champs is showing what it looks like when the back end and front end actually talk to each other.

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Holiday Shoppers Just Got Smarter

Holiday shoppers are coming armed with AI, and their expectations for personalization are higher than ever. According to the 2025 Black Friday Cyber Monday (BFCM) Forecast, 54% of consumers plan to use AI tools to find deals and compare prices. Additionally, 62% prefer AI tools that know their purchase history rather than talk to a sales associate. Shoppers are expecting brands to meet them with timely offers, personalized recommendations, and seamless experiences, no matter the month or channel.

Expert POV: If your customers are walking into holiday shopping with AI in hand, you cannot afford to show up with a generic experience. Retailers need platforms capable of delivering personalization at scale, fast and accurately, across every touchpoint. The question is not whether shoppers will use AI; it is whether your systems are ready to keep up.

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The Cost of System Failures is No Joke

Store downtime is the nightmare that keeps retailers up at night. According to a Censuswide survey of convenience fuel retailers, 98% of respondents have had to deal with system failures, proving just how widespread the problem is. Even more telling, 85% agree that keeping systems running continuously directly increases revenue by preventing lost transactions.

Kitestring’s Take: Let’s be real, retailers don’t just know these numbers, they practically have them tattooed. The upside is that new architectures and resilient platforms mean downtime does not have to be an inevitability. With the right tech foundation, you can stop treating outages like a cost of doing business and start treating uptime as a competitive advantage.

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Swipe Fees Under Fire

NACS is teaming up with Rovertown to push for swipe fee reform, spotlighting how card fees continue to squeeze both retailers and customers. With pressure mounting from all sides, the effort signals growing momentum for systemic change in payment processing.

Our Thoughts: As inflation keeps pressure on household budgets, unchecked fees from Visa and Mastercard only make matters worse. Reform is a necessary step, but it won’t be enough on its own. The real solution lies in building modern payment systems that introduce competition, transparency, and choice. When retailers have alternatives beyond the entrenched card networks, customers will finally see relief where it matters most: at the register.

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Thanks for Reading!

At the core of these articles is a simple reminder: retail advantage comes from connection, not coincidence. Whether it is tackling downtime, building hardware ecosystems, or delivering personalization at scale, the edge belongs to those who treat technology as an enabler of experiences, not just operations. Keep your systems resilient, your data in sync, and your customer lens sharp. That is how you stay ahead behind the counter!