Change is hard. No one really likes it. But, in retail more than any other industry, it’s a necessary evil.
Retail is in a constant state of change. So for us (as vendors) and you (as retailers) to be good at what we do, we have to change too.
That doesn’t mean it isn’t scary.
Go to any business in the world and start talking about changing systems then watch as anyone involved in the project starts running for the hills in wide-eyed fear.
We get it. POS implementations have a reputation for being long, complicated, and exhausting - draining time, energy, and resources while dragging on far longer than expected.
There are integrations to figure out, data to migrate, store teams to train, and a million moving pieces that need to click into place.
There’s a lot that can go wrong. And when it does, the consequences aren’t pretty - frustrated employees, operational disruptions, lost sales, and, worst of all, a system that doesn’t deliver what was promised.
It’s no wonder that, according to Gartner, half of all retailers regret a software purchase made in the past year, with poor onboarding and lack of support being the biggest culprits. But here’s the thing: it doesn’t have to be this way. With the right team, the right approach, and the right POS partner, implementation can be fast, smooth, and effective.
Avoid these five common mistakes, and you’ll be well on your way to a smooth roll out that sets your business up for success.
1. Not having the right project team in place
The team behind your roll out is absolutely key to how quickly and effectively you’ll be able to implement a new POS. A well-structured team isn’t just a nice-to-have - it’s the foundation of a success.
The mistake:
Rolling out a new POS isn’t just an IT project - it’s something that will impact your whole business. Yet, many retailers assume their existing team can handle it without considering the complexities involved. Without the right mix of skills - especially in integrations, data migration, and troubleshooting - delays stack up, errors creep in, and frustration mounts. Before you know it, what should have been a smooth transition turns into a never-ending headache.
How to avoid it:
Assess your team capabilities: Take an honest look at your team’s skills and availability. Identify gaps in technical expertise and project management.
Partner with external experts: Work with POS experts, integration partners, or external support where needed.
Define clear roles: Define clear roles and responsibilities within the project team to keep things moving.
Top tip:
Appointing a dedicated project manager with decision-making authority ensures the rollout stays on track. Fewer people in key meetings means quicker decisions and fewer delays.
"The success of the rollout came down to two key factors: the strength of the product and the people behind it. You can’t roll out that many stores without a rock-solid product, but more importantly, it was the dedication and expertise of the team that made it happen. "
- Dane Lickteig, Architect and Administrator at Rally House
2. Not involving store staff early enough
Your store staff are the heartbeat of your stores. It’s your staff who will be using the new POS every single day. It needs to work for them, you need their buy-in, and you need their expertise.
The mistake:
Retailers often focus on the technical setup but forget about the people who will actually use the system - store staff.
Involving store managers or key store associates early in the process provides on-the-ground insights that are vital for successful implementation. They can offer feedback on daily processes, customer interactions, and potential pain points. This level of involvement makes for a more practical solution that addresses the real needs of store staff, increasing adoption and making training more efficient.
How to avoid it:
Early engagement: Get store teams involved early by gathering their feedback on must-have POS features.
Hands-on training: Provide hands-on training well before go-live day.
Designate POS champions: Designate knowledgeable staff in each store to assist colleagues with the transition.
“It was very important to involve the whole organization. We wanted to make sure that we had the store associates onboard and we wanted to make sure that we really met their needs."
-Henning Fladland, Product Manager, Tech Sales, Varner
3. Choosing a POS system that is hard to scale
For ambitious retailers, we believe, the sky truly is the limit. If you’re good at what you do, your customers love you, and people go crazy for your products, then you’re probably going to want to grow. And if you want to grow, you better make sure you have tech that can grow with you. You also need to ask yourself this - can you really afford to stand still?
The mistake:
Opting for a POS system that only meets your current needs can backfire as your business grows. Without scalability, you may have to reinvest in a new system sooner than expected.
How to avoid it:
Opt for cloud-native solutions: Select a cloud-native POS that supports multiple locations and unified commerce.
Ensure seamless integration: Ensure the POS integrates easily with your existing tech stack (ERP, eCommerce, CRM).
Choose SaaS-based model: Choose a provider with a SaaS-based model to ensure automatic updates and improvements.
A scalable POS future-proofs your business, allowing you to expand seamlessly without the need for a costly system overhaul.
“We have an item database of a million plus SKUs that we know by next year is going to be pushing two and half million... so we needed a POS that had the ability to scale up to our entire inventory, handle instantaneous lookups, and be truly in sync with our our ERP.”
- Dane Lickteig, Architect and Administrator at Rally House
4. Forgetting about your customers during the transition
Your customers don’t care if you’re rolling out a new POS - they just want a smooth, hassle-free shopping experience.
The mistake:
If your transition isn’t managed properly, your customers will be the first to feel it. Long checkout lines, failed payments, and frustrated store associates can quickly turn a routine shopping trip into a nightmare.
How to avoid it:
Here’s what luxury Danish department store, ILLUM, did to ensure minimum disruption.
ILLUM’s Inspiring Implementation
The implementation of ILLUM’s new POS required meticulous planning to ensure a smooth transition with zero disruption to store operations.To minimize downtime, ILLUM’s full system transition was executed overnight in a highly coordinated operation.
Monday, 8:00 PM
Store closes after processing the final transaction on the old POS system.
Closing down and verifying the complete transfer of transaction data.
Hardware deployment & system switch
Distribution of 130 new POS systems across all departments.
Dismantling and removal of 130 legacy PC-based POS units, requiring significant space and logistics.
Installation of new hardware, including iPads, stands, receipt printers, cash drawers, and handheld scanners.
Connecting all devices to ILLUM’s internal network.
Data conversion & synchronization
Migrating 500,000 products from the old system.
Ensuring all POS systems were synchronized for real-time transactions while also enabling offline functionality.
Bank terminal configuration & testing
Installation and configuration of 130 new Adyen bank terminals at each POS station.
Verifying seamless payment processing and transaction stability.
Tuesday, 8:30 AM
All POS systems are live and fully operational.
Data migration and system validation completed.
Tuesday, 10:00 AM – Official go-live
The new system is fully activated, marking the beginning of ILLUM’s modernized retail operations.
A dedicated task force of 10 experts from Sitoo and ILLUM deployed across all five floors to provide real-time, on-site support.
Post-go-live optimization & support
Real-time monitoring of system performance.
Ongoing training and support for store associates to maximize efficiency.
Fine-tuning of omnichannel features based on initial user feedback.
The successful execution of this overnight transformation meant zero operational downtime and immediate business continuity.
5. Not having a post-roll out support plan
Ongoing relationships with software vendors are one of the most important factors that affect long-term success. It’s why it’s so important to choose a vendor you know you can have a great working relationship with.
The mistake:
Once the new POS is live, many retailers assume the job is done. But without ongoing support, minor issues can snowball into major headaches.
How to avoid it:
Partner with supportive vendors: Partner with a POS provider that offers 24/7 customer support.
Develop internal resources: Create an internal troubleshooting guide for staff.
Schedule regular reviews: Schedule periodic system updates and performance reviews.
Top tip:
The best POS providers don’t just sell you software - they act as long-term partners to ensure your system runs smoothly.
“Sitoo ticked all the boxes. Together, we’ve been dynamite, in my opinion. We’ve had brilliant project leaders from Sitoo, following up every step of the way and making life easy for us.”
-Henning Fladland, Product Manager, Tech Sales, Varner
In summary
A smooth POS roll out requires planning, testing, and staff engagement. By avoiding these common mistakes, you can ensure an easy transition and set yourself up for long-term success.
Want to make sure your rollout goes smoothly? Avoid common pitfalls and get guidance in our POS implementation playbook.
Last updated: november 14, 2025
