Rolling out a new POS system for your business is not as easy as it once was. Once upon a time, when all you had to think about was logging transactions and taking payments, replacing an old checkout was a straightforward plug-and-play purchase, with only a modest amount of configuration required out of the box.

But times have changed and POS systems have gotten a lot more sophisticated. They sit right at the heart of retail operations, connecting multiple processes beyond sales – inventory, ERP, CRM, perhaps even retail media management. Checkout is no longer a single thing – you might blend fixed-position terminals with self-service kiosks and mobile POS tablets, for example. And have all of that hooked up AI-powered sensors and cameras feeding real-time observational data into the system, and digital signage and shelf labels to create a more dynamic and engaging customer experience.

Rather than a single POS terminal in a single box, you have to think about several different types of devices and multiple additional hardware components. You have to think about network connections. You have to think about software installations and integrations. If you want your new POS to be AI-ready, you might have to think about edge computing infrastructure to ensure fast, reliable data processing at high volumes.

With all of that to consider, POS upgrades have become full-blown transformation projects. And statistics suggest that a lot of retailers are struggling to get to grips with that. 60% of retailers report that they are losing money from POS setups because of poor system integration, and 39% say they spend more time fixing system issues than they do focusing on improving performance. That’s the opposite of what a system upgrade is meant to achieve.

The problem isn’t isolated to retail and POS. McKinsey famously published a stat suggesting that 70% of digital transformation projects fail, while Bain & Co followed that up with the slightly softened finding that 88% fail to achieve their original ambitions. One of the key issues highlighted by Bain & Co is a lack of long-term strategic thinking in transformation projects. Businesses see go-live as the goal, rather than sustained performance long-term. They judge a successful rollout as ticking off a checklist of tests, rather than as building solid operational foundations that will allow the new technology to deliver.

Why POS Rollouts Break Down After the Pilot

There are some famous examples of POS rollouts going horrendously wrong. In 2015, Target had to abandon its expansion into Canada completely because an oversight in its inventory data – failing to switch from inches used in US specs to cm as used in Canadian warehouses – brought its whole logistics system down, to the cost of $5.4bn. The likes of Lidl, Nike and Revlon have been burned to the tune of hundreds of millions of dollars by similar inventory and ERP-related failures.

These extreme examples tend to cluster around software configuration, especially data. But hardware setup and integration is just as important, not least because of the impact it can have on store data and data visibility.

So what exactly goes wrong in POS rollouts when the long-term planning and strategic oversight isn’t up to scratch? Here are four common mistakes.

1. Failing to consider how system complexity increases at scale. Pilots are by definition limited test runs. You might run a new system in a single store to see how everything performs in real-life conditions. Or, for smaller businesses, test integrations in isolation or for a limited time. But the tests are by definition limited in scope, and therefore easier to ‘pass’. Things are different when you expand that one isolated system to a dozen stores. Or a system has to handle the peaks and troughs of operations over weeks and months. This is where the quality and the logic of your integrations gets tested out. Does the way you have everything connected make sense? Is the architecture designed for maximum efficiency and smooth running, or is that itself a barrier?
2. Infrastructure Isn’t Fully Prepared. POS systems are performance-critical. Even small delays at checkout impact customer experience. Under real-world load, issues like network latency, database strain, or hardware limitations that weren’t there in testing can quickly surface. A common issue is that businesses rush to roll out the latest cutting-edge tech (we’re seeing this a lot with AI at the moment) without upgrading the legacy infrastructure underneath. The result is often performance well below what was expected, delays and ballooning costs as workarounds are sought.
3. Training and Change Management Fall Short. POS systems don’t work in a vacuum. They need people to make them function successfully. And people need support in using new systems to their maximum capabilities. Not only that, they are the front line in spotting and even solving issues as they occur. For that, they need to understand how systems work at a high level. And that requires more than showing them how all the buttons work during a one-off training session.
4. Treating issues in isolation. Once the installation project is finished, there’s a tendency to react to any issues as they occur. You might call it maintenance whack-a-mole. And like that game, every time you hit one problem, another one pops up. That’s because modern POS is a complex system, and you’re not going to solve issues by treating the symptoms only. Effective maintenance has to be holistic and proactive.

Next time out, we’ll take a look at what it takes to make a POS rollout project successful, drawing on our decades of expertise in installation project management, staging & configuration, and ongoing maintenance and support.