Barcode to Backend: March’s Retail Wrap Up

Smart Systems, Smoother Checkouts, Stronger Connections

March 31, 2025

Hello Reader,

Welcome to the inaugural issue of Behind the Counter, Kitestring Technical Services' monthly insight into the evolving retail technology landscape.

Behind the Counter is designed for technology leaders, strategists, and practitioners at the forefront of retail digital transformation. As experts navigating the critical intersection of commerce and technology, you face the challenge of balancing innovation with operational stability. Our goal is to provide thoughtful analysis of emerging trends, practical implementations, and strategic opportunities that are genuinely reshaping the retail technology ecosystem.

Each month, we'll cut through the noise to highlight the innovations that are delivering measurable value, the strategic shifts worth your consideration, and the technological advances that warrant your attention.

What Retail Execs Really Want in a POS System

Retail execs are making their POS preferences loud and clear: they want all-in-one systems that just work. 83% prefer buying hardware from a single manufacturer, and while the cloud vs. on-premise debate rages on, 55% still lean toward keeping things in-house for control. Payment flexibility is a must (because no one likes being locked in), and self-checkout is officially the cool kid at the retail tech table. But even with all these upgrades, integration headaches and security fears are still very real.

Kitestring Take: Retailers aren’t just shopping for POS systems, they’re looking for a tech partner that won’t give them commitment issues. The demand for seamless integration and flexibility proves that retailers are tired of clunky, mismatched tech stacks. If vendors can’t deliver smooth, stress-free solutions that play nice with existing systems, they’re getting left on read.

Target’s AI Knows What You Want Before You Do

Target is doubling down on generative AI, moving beyond holiday gift recommendations to a more personalized shopping assistant. The new tool analyzes social trends, purchase history, and customer interests to surface products shoppers didn’t even know they needed. It’s all about making discovery easier and keeping customers engaged with hyper-relevant suggestions.

Kitestring POV: Target is proving that AI isn’t just a gimmick; it’s the next evolution of retail’s golden rule: know your customer. Their iterative approach- deploy, learn, refine, repeat- is how brands should be thinking about AI adoption. The retailers that get this right won’t just follow trends; they’ll shape them.

“To drive a valuable loyalty program, it’s critical for brands to understand consumer behaviors and preferences.”

-The Annual Report on Consumer Loyalty Expectations and Preferences

Loyalty 2.0: More Than Just Points and Perks

Loyalty programs are getting a much-needed upgrade. Customers aren’t just looking for discounts; they want real value, personalized experiences, and brands that actually understand them. Deloitte’s Annual report dives into how retailers can move beyond transactional rewards to create loyalty programs that feel less like data grabs and more like true customer engagement.

Kitestring Insight: People want connection, not just coupons. The best loyalty programs don’t just track purchases; they build relationships. Retailers that focus on personalization, meaningful rewards, and customer trust will win the long game because loyalty isn’t bought; it’s earned.

AI shopping assistants, voice commerce, and social shopping are rewriting the rules of retail. Consumers now expect seamless omnichannel experiences, and retailers are racing to keep up. From automation to AR-powered try-ons, the goal is clear: blend digital and physical shopping into one frictionless experience. And at the center of it all? POS modernization is making checkout smoother, smarter, and more flexible than ever.

Kitestring’s Thoughts: POS isn’t just a machine. It’s the heartbeat of modern retail. Smart retailers aren’t just upgrading hardware; they’re building a checkout experience that’s fast, flexible, and built for the way customers actually shop. Mobility, integrated financial tools, and real-world usability matter more than raw speed. The best approach is to plan for flexibility, focus on ROI, and don’t wait until mid-rollout to realize your system isn’t up to the task.

Explore all 7 trends transforming retail →

"Rather than selling new products at increasing speeds, only for them to end up in landfills within a year or two, circularity aims to create a value chain that slows and closes the material loop."

-Lilian Bories

Smarter, Greener, More Resilient: The 2025 Supply Chain Playbook

Supply chains are getting a serious glow-up in 2025! Retailers are diversifying suppliers to dodge disruptions, letting AI drive smarter decisions, and embracing circularity to cut costs and waste. Real-time data, flexible sourcing, and transparent sustainability efforts are essential for staying competitive. The brands that future-proof now will be the ones leading the pack.

Kitestring Take: Sustainability is a survival strategy, not just a side quest. Retailers weaving AI, diversification, and circularity into their core operations will outmaneuver those stuck in reactive mode. The smartest brands aren’t just mitigating risks; they’re turning resilience, agility, and transparency into a competitive edge.

Security Spotlight: Are You Ready for New PCI DSS Requirements?

Like clockwork, the rules for keeping cardholder data secure are evolving (again). Staying compliant is a marathon, not a sprint. Keep ahead of audits by identifying and addressing potential gaps before they become headaches.

Kitestring Perspective: Security is a never-ending battle, and PCI is a continual moving target. It’s important to stay on top of this topic and not get complacent. We strongly encourage retailers to keep their eyes on this bouncing ball and to stay out ahead of the moving targets. Fix vulnerabilities before they turn into fire drills, and make sure you know what’s coming before the auditors do. No one likes an unpleasant surprise, especially when it comes to data security.

Podcast Pick: Acquired- Costco

Ever wondered how Costco became a retail powerhouse? This widely applauded deep dive unpacks the company's obsession with low margins, high volume, and a no-frills approach that keeps customers and shareholders happy. From its legendary $1.50 hot dog combo to its surprisingly high wages, Costco proves that treating both employees and customers well isn’t just good ethics; it’s good business.

Kitestring’s View: Costco’s success isn’t just about bulk discounts; it’s about building trust. Paying employees well, keeping prices low, and resisting short-term profit grabs have made it a model of ethical, sustainable retail. In an industry where cost-cutting often comes at the expense of workers or customers, Costco proves that long-term loyalty beats short-term wins every time.

Smarter Displays, Better Sales

Retailers are upping their game with POS and IoT tech that does more than just process transactions; it observes, adapts, and sells. Smart displays can now track which setups grab the most attention, giving retailers real-time insights to fine-tune layouts, promotions, and product placement. Add in IoT-enabled beacons that send personalized offers to nearby shoppers, and suddenly, in-store shopping feels as dynamic as online.

Kitestring Insight: Data-driven displays are a game-changer! Knowing what catches a shopper’s eye means retailers can design stores that actually drive engagement (instead of guessing what works). The future of POS isn’t just about speed, but intelligence, and the retailers who embrace it will be the ones winning at in-store experience.

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Thanks for Reading!

As the retail landscape continues to evolve, staying ahead requires a strategic balance of innovation, security, and customer connection. We’re excited to navigate these changes with you! See you next month for more insights from Behind the Counter!