30-Second Summary:

  • Migrating an existing point of sale system gives you more to think about than setting up from scratch.
  • It’s crucial to determine how much of the work the provider will do, and how much you will need to do yourself.
  • Timing is everything: don’t undertake a migration when your business is busy!
  • Always ensure you have a plan to revert to your old system if the implementation goes wrong.
  • You should give some serious thought to how much of your existing data you plan to move across to the new system.

The perfect time to find the best point-of-sale system for your business is before you open your doors to the public. You have time to think through exactly what you need, and an opportunity to begin with a completely clean slate.

However, many people choosing a point of sale system are NOT starting from scratch. If you already have an established business, switching systems can feel rather intimidating. You need to do it while the business is operating, and you also have to think about how to manage all your existing data and integrations.

This article is here to provide some advice to those planning to migrate their point of sale system to a new platform. It needn’t be unduly stressful IF you plan properly and take the right precautions.

With that in mind, let’s dive straight in.

What Support Will Your Provider Give You?

Some popular point-of-sale systems for small business use (usually at the more affordable end of the market) are “off-the-shelf” systems. These are sold with the assumption that you’ll do most of the implementation work yourself – though there’s obviously a support team there to help with any queries.

At the other end of the scale are more bespoke (and usually more expensive) systems. Typically these are the kind of solutions where there’s no set pricing structure, and you’re encouraged to contact the sales team to obtain a quote based on your exact requirements.

There’s an important reason for pointing out this distinction. If you’re migrating an existing point of sale system, you’ll definitely want to know exactly what kind of assistance you can expect.

As an example, Heartland Retail offers various migration packages, where the company’s team will help you move your existing products and data. Many providers offer similar, but you’ll need to research exactly what’s involved. On the flip side, companies like Square don’t offer anything nearly as detailed, so you can expect to do more leg-work yourself.

The key question here: how much will the company do, and how much will you be expected to do yourself?

Migrate or Start from Scratch?

Let’s say you already have a fully functional point of sale system but have decided to move to a different platform.

A very important decision is whether you’re going to start from scratch – uploading new product data and fresh images, or whether you will attempt to move over what you already have.

And that leads us neatly onto the next point:

What About Historical Data?

A fresh new system provides you with a good opportunity to “clear the decks” and build systems for your store(s) or restaurant(s) with firm foundations.

However, if you’ve been in business for some time, you will need to think about all of your existing data. Are you going to try to import ALL of that into the new system?

It may be that you feel you have enough in your accounting package or other systems. Conversely, perhaps you intend to move every possible piece of data into your new solution.

Only you can answer these questions, and they’re as many process questions as technical ones. You may only have minimal data to worry about, but perhaps you have things like customer records that would seriously impact your continuity if you were suddenly without instant access to the information.

This stuff is worth detailed consideration. You can be sure that the providers of all popular point of sale systems will have been asked the relevant questions plenty of times before – so ask if you’re uncertain.

When is the Best Time?

This is a tricky one.

Arguably there’s never a particularly convenient time to start pulling out and replacing the technical foundations of your business – but there are undoubtedly better times than others.

Perhaps you open for shorter hours on Saturdays and close on a Sundays. This could well apply to you if you run a retail business. In this case, a weekend could be the perfect time to “push the button” and complete the final move over to your new system.

However, if your business is a bar or restaurant, the opposite is probably true. In that case, maybe the quiet days at the start of the week would be ideal.

What you are looking for here is some uninterrupted time to work on the implementation and – ideally – a plan to go live at a quiet moment. This will give you the opportunity to iron out issues, and get yourself and your team familiar with the new user interface – when they’re not under too much pressure.

What you DON’T want it to go live with a new POS system on your busiest day or night of the week. That’s a BAD idea!

What’s the Regression Plan?

One thing every technical project should have is a regression plan. This basically means that you know exactly what you’re going to do if, for whatever reason, you determine that the system isn’t suitable, or quite ready to put into action.

There are some fundamentals here that you must get right. Don’t uninstall the software for your old system until you’re absolutely certain you won’t have to go back to it. To be safe, this could mean weeks or months, so that you have some insurance if the new solution doesn’t work out.

On the same theme, this means not cancelling any subscription you may have to a previous product until you’re sure you’re happy. And if you use an on-premise solution, don’t wipe the existing server to use for the new system!

One very useful thing to build into a regression plan is a firm “stop or go point.” For example, you can say that you need the system completely functional, with test transactions completed, by 5pm the day before you go live.

If, for whatever reason, you cannot tick that box, you then implement the plan to go back to what you were using before, until you resolve the issues. You may even decide to abort the project altogether.


A big factor in many IT projects going wrong is poor planning, and failing to identify things that might go wrong.

The advice here should minimize the chance of that happening, and ensure you choose the best point of sale system for your requirements. If you’re doing a migration, the considerations will be rather different, compared to a new system for a new company.

Teething problems are common with any technical implementation. However, with the right planning, you will quickly come out to the other side with the best point of sale system for your business.