Prepping for POS Success: What Retail Leaders Should Know Before Upgrading

Less than half of retailers (47%) say their POS system supports an innovative or differentiated store experience, according to a recent study published on GlobeNewswire. That is concerning, because when the point of sale is not enabling innovation, it is holding the business back. The POS is not just a checkout tool. It is the heartbeat of retail: where revenue happens, where customer impressions are made, and where smooth operations make or break the experience. But for many retailers, the POS system running that heartbeat is showing its age.

Why Retailers Decide It’s Time to Upgrade

Let’s get one thing clear: most POS systems still work. If they didn’t, you wouldn’t be in business. There often isn’t a direct, urgent need to replace a POS because it is broken.

The reality is that many retailers operate with systems that are far from optimized. These platforms may still function, but they introduce friction, slow down innovation, and fail at critical points.

So, what pushes retailers to finally say it’s time?

• Speed to market. Modern retail moves fast. If new ideas take four years to execute, you’re already behind.

• New capabilities. Whether it’s launching high-speed diesel or rolling out a new loyalty program, legacy systems can make even simple additions costly or impossible.

• Outdated user experience. An old-school interface not only slows down adoption but makes your brand feel behind the times, especially to younger employees and customers.

• Diversifying revenue. As traditional categories like fuel and tobacco decline, retailers need modern systems that can support new service offerings.

• Reducing fragmentation. Running multiple POS systems under one roof is inefficient and expensive. Leaders are looking for unified, flexible solutions.

It’s not about replacing something that’s broken. It’s about creating space for your business to grow and compete.

I Know I Want to Modernize, Now What?

Once the decision to upgrade your POS is made, the next step isn’t picking a vendor or scheduling an install. It’s taking a hard look at your internal landscape and getting your foundation in place. That groundwork makes all the difference between a smooth transformation and a drawn-out struggle.

Here’s where to start:

• Figure out your business case.

  The costs can be significant. Five million dollars for a smaller retailer, upwards of twenty million for a large chain. That kind of spend  needs justification, and more importantly, executive approval. Build a case that answers, “What do we get from this investment?”

• Identify your pain points.

  Go beyond “I don’t like this system.” Ask: What’s slowing us down? What support issues are we paying for year after year? Where are we spinning our wheels? The answers often come straight from store teams and ops. Listen to them.

• Map your architecture.

  Before you move anything, understand how your POS interacts with the rest of your tech stack. This includes everything from inventory and payments to loyalty and ecommerce. Having a clear diagram that shows how all these systems connect makes integration planning much smoother.

• Check your enterprise service strategy.

  If you’re still running a tightly coupled system without reusable services, integration is going to be a slog. Ideally, your architecture already includes shared services like payments and item catalogs that work across channels. If not, now’s the time to build that strategy.

• Assess dependencies.

  Changing your POS might mean changing, or at least touching, other systems. Don’t wait for implementation to realize that your accounting platform or back-office tools aren’t compatible.

Modernization starts long before rollout. The clearer the picture up front, the more confident every decision becomes down the line.

Should I Do It In-House?

It’s a fair question. Some retailers consider managing the POS upgrade internally. After all, your team knows your business best. But there’s a catch: they also have to run that business.

A POS upgrade isn’t a side project. It’s a multi-month initiative that demands time, focus, and specialized expertise. For most companies, pulling internal resources full time just isn’t realistic.

Ask yourself:

• Can you afford to dedicate half your IT team to this for a year and a half?

• Can those teams research vendors, manage change, and design future-state architecture while also keeping current systems running?

• Do you have the capacity to anticipate every challenge when this might be your first upgrade in 20 years?

If the answer to any of those is “probably not,” you’re not alone. Many retailers hit the same wall. The payoff from a modern POS comes later, but the resource load hits right away. And with lean teams stretched thin, that tradeoff can stall or derail even the best intentions.

That’s where a partner like Kitestring comes in. We understand the integration challenges because our team handles them multiple times a year. We bring in frameworks, vendor relationships, and lessons learned so you’re not starting from scratch. And we help your internal team stay focused on what they do best: keeping the business running.

Aligning People & Process for Change

Even the best technology will fail if the entire organization is not bought into it. A POS upgrade reshapes day-to-day operations across the entire business. It is not just an IT project. It touches inventory, accounting, operations, supply chain, and of course, the store teams who work with the system every day. Success depends on preparing the people as much as the technology.

Here’s what works:

• Start in the stores.

  Your frontline teams are the ones using the system every day. Talk to them early. Listen to their pain points. Involve them in the decision-making process. That involvement builds trust and drives adoption.

• Get leadership aligned.

  Upgrades touch every corner of the business. Without buy-in from the top, projects stall or fail outright. Leaders must communicate consistently and make sure every department is rowing in the same direction.

• Train with intention.

  One-size-fits-all training does not work. Customize onboarding based on roles, responsibilities, and real-world workflows. Know your business and know your team.

POS modernization is as much a culture shift as a technical one. Your success depends on how well you prepare your people for what is ahead.

Common Pitfalls and Mistakes to Avoid

Even with the best intentions, POS upgrades can stumble. The good news is most of the biggest mistakes are preventable if you know what to watch for.

• Not engaging the right stakeholders.

  Too often, upgrades are treated like IT projects. In reality, they are business transformations. Leaving out store staff, the people who rely on the system every day, is a surefire way to create resistance and frustration.

• Oversimplifying the unknowns.

  Legacy systems are complex. Integrations rarely go as smoothly as expected, and hidden dependencies have a way of surfacing mid project. Underestimating that complexity leads to delays and ballooning costs.

• Competing agendas.

  Different teams often want different things from a new POS. Without strong alignment, upgrades can become tug-of-war projects instead of unified efforts.

• Adding too much too soon.

  Excitement around new possibilities is natural, but piling on features before the core system is stable creates risk. Focus on the essentials first, then expand once the foundation is strong.

Avoiding these pitfalls does not guarantee a perfect rollout, but it dramatically increases the odds of a smoother, more successful upgrade.

What Makes Kitestring Different

POS modernization is one of the toughest projects a retailer can take on. We have guided these efforts for years, across every size and scale of retail. There is not a part of the industry we have not explored.

That experience matters. It means we can walk into complex situations with confidence, knowing how to spot risks, anticipate challenges, and guide teams through them. It also means we know the players because we have already built relationships with the vendors you are trying to evaluate. We know their products, their strengths, and how they fit into different retail environments.

What really sets us apart is our ability to operate on two levels:

• We bring the strategic perspective to help you align business goals, store capabilities, and long-term growth plans.

• We bring the technical depth to understand implementation realities, so we can prepare you for the risks that others overlook.

Other firms tend to choose one lane: either high level consulting that stops at the recommendation, or pure implementation that only handles the coding and rollout. Kitestring does both. We help you define the right path forward and then walk with you through the execution. That blend of strategy and real-world scars is what ensures the work we do together actually sticks.

Ready to Modernize with Confidence?

Upgrading your POS is more than just replacing a system. It’s about positioning your business to move faster, serve customers better, and unlock new revenue opportunities.

Kitestring has the experience, the relationships, and the proven process to get you there without derailing your business along the way.

 

 

Sources

GlobeNewswire. “Retailers Are Betting Big on Brick-and-Mortar Stores for Growth, But In-Store Tech Just Isn’t Up to Par, Study Finds.” May 7, 2025. Read the full report.