Let’s be honest. Changing your tech stack can feel a bit like trying to rewire a spaceship while it’s mid-flight. There’s pressure. There’s jargon. And there’s always that one person in the room suggesting you “just migrate everything to a single platform” like it’s no big deal.
But behind the glossy promises and perfect-case-scenario playbooks, the truth is this: implementing new technology can easily be messy and emotional - because it’s deeply human.
Retail isn’t run by systems. It’s run by people. And when those people are equipped with the right tools, life gets way simpler and easier.
That’s why we’ve skipped the theory and gone straight to the source.
We’ve spoken to retail leaders, tech trailblazers, and shop floor superstars who’ve been through it all - launching new platforms, rolling out new POS systems, ripping out legacy stacks, and building better boats.
This post isn’t about best practices from the boardroom. It’s about real lessons from the frontlines.
So whether you’re replacing your POS, modernizing your entire stack, or just trying to avoid another rollout that leaves your store teams frustrated - these are the tips you need. Tried. Tested. And shaped by people who’ve done the hard work and come out stronger from it.
Let’s dive in.
Start with the end in mind: Why every great rollout starts with a clear vision
Before you sign a contract or even book a demo with a software vendor, stop and ask: What are we really trying to achieve?
It sounds simple, but you’d be surprised how many retailers skip this step. They dive into tech upgrades hoping the right tool will fix broken processes, outdated mindsets, or disconnected teams. But tech alone isn’t the answer. Clarity is.
The most successful implementations we’ve seen all started the same way - with a crystal-clear vision. The retailers knew what a great outcome looked like. They understood the needs of their teams and their customers. And they used that insight to guide every decision that followed.
Here’s what they say about it:
“Start with a clear vision. Know what you want to achieve - not just in broad strokes, but in specifics. What are your revenue goals? What kind of customer experience are you aiming for? And what functionality will you need to get there? Mapping this out from the start gives you a solid foundation and helps you make smarter decisions.” - Ben Jones, Head of Ecommerce & Technology, OSPREY LONDON
“Our approach to investing in a new POS system was guided by a deep understanding of both technical requirements and user expectations. We engaged in extensive dialogue with our staff and customers to identify their needs and pain points. This user-centric approach ensured that we didn’t just replace our existing system with a technically superior one but one that addressed real-world issues faced by our users. By documenting these insights, we could list our requirements for a POS system that not only met current demands but was also adaptable to future needs, providing a seamless and efficient shopping experience.” - Henning Fladland, Product Manager, Varner
“The most successful software implementations start by involving the right stakeholders from day one. When you minimize the back-and-forth between project managers, execs, and boards, everything moves faster and smoother. It creates space for better decision-making and a more creative, efficient workflow. But clarity is just as important - know what matters most, define your priorities early, and focus your resources there. That’s how you avoid distractions and keep the project on track.” - Kristen Liebert, Vice President of Business Transformation & Treasurer, Rally House
The secret to smoother tech rollouts: Choosing the right partners
Strong partnerships create smoother rollouts, faster problem-solving, and a whole lot less stress. So don’t just pick tech - pick people you trust to build something great with.
You need partners who don’t just understand technology - they understand you. Your challenges. Your goals. Your pace.
Because the truth is, even the best tech can fall flat if it’s not backed by the right people. The ones who show up when it counts. Who listen before they sell. Who think long-term, not just about go-lives and contracts.
Here’s what these retailers had to say about choosing the right partners:
“We wanted flexibility. We wanted systems that could evolve with us and let us plug in best-in-class tools as our needs changed. That principle shaped a lot of our decision making.
“We also knew we couldn’t do it alone. Choosing the right partners was everything. We didn’t want to be locked into specific hardware or workflows - we wanted things like an open integration approach and Android compatibility. Basically we wanted solutions that could fit around us - not the other way around.
“And it’s worth saying: this wasn’t just about ticking tech boxes. Every system we chose had to make life better - for our customers, our stores, and our teams. It’s been a massive shift, but taking the time to get it right - and choosing tools that talk to each other - has set us up for the next stage of our growth.” - Ben Jones, Head of Ecommerce & Technology, OSPREY LONDON
“I always look beyond the current requirements and think about where the company is heading... After that, it’s about the people - are they the kind of people I want to work with? Do they share our vision? It’s crucial to be on the same page.” - Peter Joelsson, CIO, Webhallen
“The strength of the product is important - but the people behind it matter just as much. With Sitoo, we weren’t just buying software, we were gaining a team that was committed, knowledgeable, and genuinely invested in helping us succeed.” - Dane Lickteig, Architect & Administrator, Rally House
“Of course, having a robust, innovative product is essential, but in my experience, a truly successful partnership is built on shared values and the people behind the brand.
“When you’re working with partners like this, the partnership works because we are both fully committed to creating something remarkable. It’s about feeling assured that no matter what challenges we might face, we’re in it together and both invested in finding the best solutions.
That’s the type of relationship we aim for with all our key partners. They need to be as driven as we are, and they need to see beyond just the current project. It’s about building for the long-term, supporting each other through ups and downs, and constantly pushing each other to achieve more.
“When your partner is not only dedicated to their product but also invested in your growth, it becomes a partnership in the truest sense - one where you’re constantly moving forward together, hand-in-hand, with a shared goal in sight.” - Mobarak Said, former Head of IT & Digitalization, Illum
Choosing tech that works now – and still makes sense after many years
Retail doesn’t stand still - and neither should your tech. What works brilliantly today might feel outdated in 18 months. That’s why the smartest retailers aren’t just solving for now - they’re setting themselves up for what’s next.
It’s about finding tools that can flex as your business evolves. Systems that don’t just plug the current gaps, but grow with you. Platforms that integrate easily, scale quickly, and let you change direction without starting from scratch.
Here’s what the experts say:
“I’m not just looking at what the system can do today but what it will be able to do tomorrow. You don’t want to get stuck with a system that meets today’s demands but becomes obsolete when your business changes.
“When we started looking at replacing our POS, we weren’t just thinking about what we needed today. We were thinking three, five years ahead. I’ve seen it happen so many times - businesses invest in a system that fits current needs, and two years later, they’re stuck again. That’s not good enough.
“So for us, the question became: ‘Will this system evolve with us?’ And if the answer wasn’t a clear yes, it wasn’t the right fit. That’s why we leaned into a best-of-breed strategy. Instead of one giant system doing everything halfway, we chose multiple systems that each do one thing exceptionally well. It’s a bit more work to integrate, sure, but the payoff in flexibility and performance is worth it every single time.” - Peter Joelsson, CIO, Webhallen
“For us, it was never just about replacing our POS. It was about future-proofing the business. We took a holistic view - how would this system support store staff, streamline operations, and scale with our inventory growth? We asked tough questions and looked for a partner, not just a vendor.” - Dane Lickteig, Architect & Administrator, Rally House
“Embrace agility. Retail is evolving faster than ever, and the ability to change direction quickly is invaluable. Don’t be afraid to experiment, try new things, and learn from the results. Retail tech is not a one-time investment; it’s an evolving relationship, one that should grow and adapt alongside your business. Think of tech transformation as a partnership - your systems, your people, and your goals need to move in harmony. Stay open to innovation, be ready to pivot, and keep refining your approach based on what works best for your customers and your teams.” - Mobarak Said, former Head of IT and Digitalization, Illum
Be brave. Be ambitious. And set the bar high.
Playing it safe won’t get you where you want to go. The retailers leading the pack right now aren’t the ones tweaking around the edges - they’re the ones making bold moves, moving fast, and refusing to settle for ‘good enough.’
Being brave doesn’t mean being reckless. It means backing your vision. It means choosing partners who can move at your pace. And it means setting a standard that reflects not just where you are, but where you want to be.
So aim higher. Roll out faster. Build better. Because the bar isn’t where it used to be - and neither are your customers’ expectations.
Just like these retailers are doing:
“Previously, we were twisting new tech to fit old structures - and it was painful. This time, we did it differently. We started with the customer experience we wanted to create and built backwards. That meant replacing the entire stack - from PIM to payments to shipping. We were finally building tech that made sense for our future.” - Mark Oldham, Commercial Director, Ellis Brigham
“Don’t be afraid to take risks. The safe choice is often sticking with a monolithic system, but that can actually be the riskier move in the long run. Best-of-breed solutions can give you flexibility and scalability, but you have to be willing to embrace change and not shy away from it.” - Kristen Liebert, Vice President of Business Transformation & Treasurer, Rally House
“After a couple of years of major change - swapping out our entire tech stack and overhauling how we operate - this year is about consolidation. We’ve laid the groundwork. Now it’s about refining, optimizing, and really making sure we’re getting the most out of everything we’ve built. That in itself is exciting - because now we get to shift our focus from transformation to elevation. From ‘what do we need to fix?’ to ‘what can we make even better?’” - Ben Jones, Head of Ecommerce & Technology, OSPREY LONDON
Final thoughts
Tech implementation isn’t easy. It takes time, commitment, and more patience than most people like to admit. But what these stories show is that it’s absolutely worth it.
When you lead with clarity, choose the right partners, build for both now and next, and back your ambitions with action - you’re not just upgrading systems, you’re creating a retail experience that’s faster, smarter, and more human.
Set the vision. Find the right people. Keep moving forward.
You’ve got this.
Ready to take the next step?
Download the Sitoo POS implementation playbook to get practical guidance, proven strategies, and the insights you need to roll out smarter, faster, and with confidence.
Last updated: June 26, 2025
