Upgrading to a new POS? 10 Industry Experts Share Their Best Advice About Replacing Legacy Retail Systems

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Consumers these days are smarter, savvier, and — to put it bluntly — more demanding than ever.

Not only are they shopping across physical and digital storefronts, but they expect to have the same great experience as they move from one channel to the next.

Oh, and they want you to offer products at great prices and fulfill orders in the fastest and most affordable way possible.

Those are some very high expectations, and you can’t meet them using legacy retail systems. To fulfill the demands of modern consumers, you need to arm yourself with a powerful retail solution that provides tools for managing products and customers across multiple stores and touchpoints.

It’s a big ask, but it’s something you need to do if you want to stay in business.

If you’re looking to move from a traditional retail system but aren’t sure how to go about the process, keep reading. We tapped into the retail community and asked retail and technology experts to share their best advice for merchants replacing their legacy retail management system.

Have a look at their insights below and keep them in mind when you’re in the process of upgrading your retail solution.

1. Start with the customer.

Start with the customer. What’s their ideal world? What will the system need to deliver? Map that versus your system’s current capabilities and you’ll have begun the process of building out a skeleton business requirements document.

– John Ritchie, E-commerce & Multichannel Marketing Manager at Dobbies Garden Centres

It can be easy to get wrapped up in what you need in a retail management system, but don’t forget to who you’re doing all this for — your customers. Rather than focusing solely on what you require, figure out the ideal shopping experience from your customer’s perspective and then choose a system that can deliver that experience.

2. Business before IT.

The business needs to articulate their “why” for this project then tie that in with where they want to be 5 years from now. Retailers must also define their priorities in such a transformational project, and from there, develop the IT strategy supporting the new retail management software (e.g. in-house build, off-the-shelf, on-demand / on-premise, support / maintenance, etc.)

– Jan Michael Jaudian, VP of Software Design & Chief Solution Architect at TransMobilize Inc.

Before diving into the technical details of replacing your retail management system, make sure you’ve clearly defined your business objectives. Why are your switching to a new solution? How will it fit into your business roadmap? Clearly defining the answers to these questions will help you navigate process so you can successfully find and deploy the right solution for your business.

3. It’s OK to make it a gradual process.

A solution doesn’t have to be implemented all at once. You can implement it in a very staged, careful fashion, as long as you know what the big picture looks like. You can break things down into smaller, manageable projects while making sure you get to the place where you want to be in the end.

– Jeffrey Atizado, Joint Managing Director at SMB Consultants

Sometimes, a new solution isn’t just one piece of software – with the growth of connected apps that work together to provide a complete business package, there can be multiple elements to consider. So, it can be best to take a more gradual approach to implementing a new solution. If the prospect of launching a new retail management system across your entire operation seems daunting, break down the process into batches. For instance, you can roll out the system to a few stores before moving on to other locations. This lets you ease into the new solution and keeps you from getting overwhelmed.

Rolling out a system gradually also provides learning experiences for the business. You’re able to spot areas for improvement so by the time you implement the system in other store or areas of the business, you can do so in a smoother and more efficient way.

4. Be mindful of potential pitfalls.

When searching for a system, be aware of the pitfalls of vendor lock, inflexible APIs and the learning curve any new system presents.

-Jonathan P. L. Spooner, Retail Technology Consultant at JPlus

Don’t let a shiny new system blind you from potential issues down the line. Before signing up, think about how you’re going to transition users to the new solution. Is it easy to understand or would you need to invest resources in training?

Be sure to assess the flexibility of your new solution. Is it customizable? Do you need to modify your existing workflows? Can it integrate with other solutions you’re using? These are just some of the questions you should answer before deciding on a new system.

5. Have a process.

To me, the answer to this question boils down to one word: process. Here are some of the steps I would encourage retailers to follow: Step 1: Compile a list of must-have features; Step 2: Schedule a demonstration; Step 3: Research the company; Step 4: Request pricing ; Step 5: Run a free trial.

– Fabien Tiburce, CEO at Compliantia

Replacing your legacy retail management system is a daunting task, so get organized. As Tiburce notes, you need to have a process. You don’t have to follow the steps outlined above if they’re not a good fit for your business. But the point is to set up a procedure that can keep you on track. When it comes to big projects like this, the last thing you want is to be “all over the place.”

6. Consider bringing in a specialist.

The implementation of a new POS system across multiple stores requires planning, time and patience. Since your staff is already working hard at running the business, bringing in an outside specialist to focus on the transition, the training, the data conversion and everything else –  will be money well spent.

Craig L. Aberle, Publisher at The Point of Sale News

If you don’t have the resources or expertise to research, evaluate, and deploy a new retail management system, then you may want to consult with third party experts who can assist you in all phases of the project. In doing so, you’ll save time from having to sift through the numerous solutions in the market. Plus you’ll be able to tap into their technical knowledge and expertise so that you can make smarter decisions throughout the process.

7. Choose a system with robust inventory capabilities.

When it comes to replacing a legacy system, retailers need their new POS to feature a strong inventory software. Another thing to consider is whether or not the inventory data from the legacy system can be migrated to the new system.

Depending on the number of stores and the amount of products, having to go back through and redo inventory counts from scratch is something retailers don’t want to even think about. In the same breath though, there’s no reason to adopt a mediocre POS just because your current inventory data migrates to it. Retailers have to keep the future of their business in mind.

– Justin Guinn, Market Research Associate at Software Advice, a Gartner Company

The vast majority of multi-store retailers — ninety-six percent according to Software Advice — are requesting specifically for inventory management capabilities for their new POS. This comes as no surprise considering that products are the lifeblood of any retail business. That said, inventory is also one of the most challenging aspects to manage.

As Guinn puts it, “With tons of products spread throughout multiple locations, getting a firm handle on company-wide stock levels can be a huge challenge. But it’s efficiency that multi-store merchants need to achieve in order to streamline inventory management.”

Keep this in mind when searching for a new retail system. Features such as staff management and loyalty are great, but inventory should be your top priority.

8. Don’t be afraid of new retail solutions. Embrace them.

New technologies are allowing for impressive levels of accuracy in inventory control, a stunning ability to optimize your marketing and convert browsers into buyers (whether they’re in-store or online), and integrate with other software in ways that will save you time, money and headaches.

If your first thought is that this sounds a little bit out of your comfort zone, don’t worry. The tools that will connect everything from your POS system to your inventory management system to your online store to your accounting software and payroll, are now as intuitive as they are powerful. You’ll be amazed at how, all of a sudden, things just work together.

Ian Atkins, Analyst and Staff Writer at Fit Small Business

Don’t let fear of new technology get in the way of innovation in your business. Yes, switching to a new platform can be overwhelming and intimidating but when you do it right (i.e. do your research, follow a process, and/or hire a consultant if necessary) you’ll find that the payoff is well worth it.

9. Test, test, test.

Testing out new software is always a huge plus. You’ll want to make sure everything runs smoothly and can be modified to the needs of your company. Front of house operations, inventory and accounting will probably be the most key items to keep in mind during testing. Integration with ability to handle shipping, receiving and other tasks may come in handy for the business as well.

– Cindy Buentello, Apparel and Footwear Specialist at Edwin Watts Golf

Modernizing your retail management system will take a sizeable investment, so you want to make sure you get it right. The best way to do this is to thoroughly test the system to ensure that it works for your business. 

For best results, test it in the real world. Deploy it at an event or a popup store. Or if possible, test it out in a small market or a couple of stores before rolling it out across all your locations.

10. List your “need to have” features first.

First things first: you need to make a list of features you cannot live without. Next make a list of features you want, but could live without. Finally, set a budget.

Once you know what you need, you can start looking. After some searching, and using a database like Capterra, narrow your search down to 5 solutions. Make sure to spend time talking to their sales reps, and take advantage of free demos or trials to really get to know the software.

If you love a certain software, but it doesn’t quite have everything you need or want, make sure to talk to the sales rep about it. Companies are often able to build special integrations, or even full features, custom in order to make sure their customers have everything they need.

– Cara Wood, Capterra

When it comes to determining the features your next retail solution should have, be sure to create a “need to have” and “nice to have” list. It sounds simplistic, but if you aren’t clear on the features you that you absolutely need versus the “nice to haves,” you could get sidetracked and end up with a beast of a project.

To make things easier, look into the functionalities of your current system. What are the things it can do now that you need in your new system? Then, look into existing pain points. What issues do you want to overcome with the new solution? The answers to these questions will enable you to identify the features you require. From there, you can proceed to listing out capabilities that are “nice to have.”

How long should the process take? Wood advises retailers to allocate six weeks to for the search as “this is the average length of time companies are able to find a replacement software in.”

Further Reading

If you need more info on how to effectively compare different point of sale solutions, download Vend’s POS Buyer’s Guide. In this resource, you will learn the 7 secrets to find a reliable POS system, and avoid the costly mistakes most retailers make when choosing a new retail platform.

In it you’ll learn:

  • How to budget for your POS system
  • How to find and vet providers
  • How to get the most out of the solution

Learn More

Weigh in.

Do you have any advice for retailers who are looking to switch to a new retail management system? Let us know in the comments.


About Francesca Nicasio

Francesca Nicasio is Vend's Retail Expert and Content Strategist. She writes about trends, tips, and other cool things that enable retailers to increase sales, serve customers better, and be more awesome overall. She's also the author of Retail Survival of the Fittest, a free eBook to help retailers future-proof their stores. Connect with her on LinkedIn, Twitter, or Google+.

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