How to Find the Right POS Software for Your Retail Business (An In-Depth Guide)

This is a post by Merhawi Kidane

Retail businesses owners and employees understand the frustrations that come with using outdated technologies in their business operations.

Old cash registers are clunky, an eyesore, and sometimes aren’t able to perform modern (but increasingly necessary) tasks such as integrating with your inventory or accepting mobile payments.

That’s why retailers today should have point of sale (POS) software that can handle anything their merchants and consumers can throw at it, along with providing features that makes running your business easier.

Why continue with an outdated system when you could have sales reports, inventory control, and loyalty marketing all at the tip of your fingers?

This is where modern point of sale systems come in. Great POS software will make sure that your cashiers won’t run into any trouble when your customers are ready to checkout. It’ll make the handling of inventory a snap for when you receive shipments, along with building sales reports so that you can adjust your marketing strategies accordingly.

“Alright, I’m sold! But which one do I go with when there are so many choices?”

If you’re asking yourself that question, fret not.

We’re here to give you a step-by-step guide to make sure that you choose a POS system that’s perfect for your business.

Step 1 – Understand your needs: What should you look for in a POS system?

Purchasing a POS solution is a big decision that will affect your business operations the day you install it. That’s why it’s critical to understand what you’re looking for right off the bat.

When looking at solutions take note of any “must have” capabilities that you need in your store.

For example, many pop-up stores prefer to use iPad POS systems because they’re portable and work great in tight spaces. Meanwhile, multi-store retailers typically opt for sophisticated platforms that enable them to have a centralized view of their sales, inventory, and customers.

Figure out what your needs are, and then use those requirements to guide your search.

A helpful tip is to make a list with all of the features that you would need out of a POS system.

An example of features that you would look for are:

  • Cloud-based and available from anywhere, iPad, Mac or PC
  • Apply discounts by line item or total sale
  • Multiple payments and payment types can be accepted in one sale
  • Run promotions and allocate special pricing by customer list
  • Manage and track inventory across all stores

Take your time when creating your list and to ask your employees if they have a POS or retail management system “wish list.”

Also, note that comparing multiple vendors (each with their own set of features and functionalities) can get overwhelming, so you need an efficient method for evaluating solutions side-by-side. One way of doing this is to create a vendor matrix that lists all your key requirements. Once you have those requirements on paper, put the different vendors that you’re considering in separate columns, and then check off the features that each vendor can provide.

Vend Tip

Need an example of a vendor matrix you can use in your business? Feel free to use this one

Learn More

Step 2 – Consider payments: Will your POS and payment processor play nice with each other?

Accepting payments is the most crucial aspect of the POS process. No matter how amazing your products are, they will mean nothing for your bottom line if your systems aren’t able to accept payments.

For this reason, you should keep payment processors in mind when looking for a retail point of sale system. You need to ensure that your POS works well with your payment provider of choice to ensure a smooth checkout experience.

What’s a payment processor?

A payment processor is a just a fancy way of describing the avenue in which a company handles payments from credit and debit cards.

You need to understand this because not all POS solutions are compatible with every payment processor. And you definitely don’t want to be left with having to change how you accept payments after installing your POS software.

Aside from checking to make sure that the software is compatible, you want to research if the software accepts all the necessary payment types — including chip cards and mobile payments.

How do you find the right payment provider AND point of sale software?

This depends on where you are in your search. If you already have a preferred payment processor, you may want to look into the POS systems they work with. On the other hand, if you don’t have a payment provider yet, we recommend looking into POS solutions first and then asking about their payment integrations.

Whatever the case, it’s best to opt for integrated payments.

POS-integrated payments allow sales to flow directly from your point of sale system to your card reader. This provides you with several benefits, including:

  • Faster and more secure checkout: With integrated payments, you won’t have to manually key the transaction information into the card reader. This makes it easier and faster to ring up sales and also removes double entry and the likelihood of human error. Raja Chakravorti, Director, Retail & Mid-Market Partner Development at PayPal, says that opting for integrating payments can result in massive time savings for the retailer. “Using an integrated solution can help save you time and allows you to access your store’s information and accept payments all in one place. That means no more entering sales manually.”
  • No manual reconciliation: Having integrated payments also eliminates the need for end-of-day reconciliations, freeing up time that you can use to grow your business and keep customers happy.
  • Financial savings: In many cases, payment processors offer special rates to merchants using their preferred partners, so you can potentially score better rates by opting for a provider that integrates with your POS.  
  • Better visibility into your operations – Having your payments and retail technologies working together makes it easier for you to gain data and insights about your business. As Jim Roddy, Reseller & ISV Business Advisor at Vantiv says, “you get a complete picture of your numbers rather than having to cobble together different systems. You have access to advanced reporting – data that can help you make decisions which will lead to a better customer experience.” Talach adds, “a payment processor is only useful if it integrates with the other technology that makes your business run smoothly. Choose a processor that works with your POS system, so you can view all your sales data in one place and make better-informed decisions to grow your business.”

Further Reading

Need help finding a good payment provider? Check out Vend’s Retail Payments Guide. This resource will you understand the importance of payment processors in retail and will give you the confidence to choose the right one for your business.

Learn More

Step 3 – Budgeting: How much do point of sale systems cost?

Now that you have an understanding of what you are looking for, it’s time that you determined how much you’re willing to spend.

Although having to spend large amounts of money is never fun, this is going to be a major investment in your business’s future, so try not to make your decision on the premise of finding the best bargain.

With that said, when it comes to budgeting for your POS system, you need to account for the following:


Years ago, you used to be able to get away with only having a register and receipt printer as the only devices in your system.

In today’s day and age, this just doesn’t pass.

Thankfully, there are plenty of solutions in the market that give you the option of bundling your hardware with your software purchase, allowing you to get by with minimal hardware expenses.

An example of a minimal setup includes:

  • iPad
  • Credit card reader
  • Cash drawer
  • Receipt printer.

Estimated Cost: $800- $1,000

On the other hand,you may run a busy store that needs to scan items quickly and conduct partial and full inventory counts on a regular basis.

In this type of scenario, you will want a more advanced setup, an example of which could be something like

  • Computer or laptop
  • Barcode Scanner
  • Label printer
  • Cash drawer
  • Receipt printer
  • Credit card reader

Estimated Cost: $2,000-$3,000

It’s also important to decide which platform (Apple, Android, Windows) you see yourself using in the long run.

Most POS software are very specific when it comes to which platforms they support and you don’t want to make the mistake of investing lots of time and money into a software only to discover in the end that it’s not even compatible with your preferred operating system.


When it comes to cloud-based of POS software (which we highly recommend) most platforms utilize a monthly subscription model instead of a long-term contract.

This payment setup is ideal because users benefit from constant access to customer support and receiving regular updates to their systems. Plus, you’re not tied to any long-term contracts so you can switch if the solution doesn’t work out for your company.

Your price will vary depending on the number of locations you have, the overall size of your business, and whether you will be needing any extra hardware or not.

The size of your business is especially important. While a single-location business may be paying less than a hundred dollars a month, a large business with a several locations can expect to spend hundreds, perhaps thousands per month.

For example, Vend’s Starter plan costs $69 a month and includes one free register. Additional registers can be added at a cost of $39 per register, per month.

So if a retail store has two registers, their cost breakdown will be:

Base fee ………………………. $69

1 additional register …….. $33

Total monthly cost: ……… $108

Step 4 – Research: What are the best POS software solutions in the market?

Figured out your needs? Check.

Determined your budget? Done.

The next step is to actually look into the different POS systems in the market and then narrow down your search.

Our advice? Make a list of some of the top POS platforms along with some of their features and pricing. Doing so will put things into perspective when you’re researching which software solutions are best for your business.

To make this step easier, we recommend utilizing typical research avenues like industry websites, as well as YouTube, social media, and good old fashioned conversations with other retailers.

Here’s how to go about your research process:

Peruse industry sites

There are some great articles out there that go in-depth in providing reviews and comparisons of the latest POS software and hardware. Here’s an example from

If you need more information, run a Google search for the POS software provider that you’re considering and then go from there.

Watch YouTube videos

You can also watch point of sale software reviews and tutorials on YouTube, so you can have a look at each program’s interface and features.

When going this route, make sure to pay attention to the source of the videos. Most channels covering the topic belong to a  POS software company so keep in mind that the videos that you watch may contain some bias.

Turn to social media

A good place to begin is on LinkedIn, where you can find professional groups centered around POS software like the Point of Sale Network group, where you can ask any questions you might have regarding the subject.

Also, don’t hesitate to ask questions in Facebook groups for business owners like this Small Business Owners group. People here have a lot of experience with POS systems and should be able to help you with any issues you may have.

Talk to people in your space

Talk to fellow merchants about their POS system and ask how it’s working for them. Many retailers have discovered great solutions for their businesses simply by looking at what other stores are using.

Check out the story of Luminosa, a beauty retailer who switched from a manual pen-and-paper system to Vend. According to owner Ellie Burgoyne, she first came across the software at a coffee shop. “I noticed that they put the transaction through an iPad and I thought that was really cool. So I asked them about it, and that’s when I started doing my research,” she recalls.

Another important step is getting your employees involved in the process, as they are the ones that will primarily be dealing with the software. Make sure to get their input on every POS solution you’re considering as well as any options they may think is a good idea.

Taking the steps above should give you an idea of what solutions are right for your stores. Use that knowledge to build a list of some of your top choices, then reach out to the software providers to see if they can offer more information.

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

Step 5 – Take ‘em for a spin: What’s the POS system *really* like?

A POS company may look good on paper (or on your computer screen), but that doesn’t always guarantee a smooth experience.

This is the time where you put your choices to the test and to see if each solution is capable of doing what you need it to do.

The best way to do this is to take a free trial or demo of the POS software. Keep an eye out for speed, functionality, and user-friendliness for each POS solution. Can you see it getting along with you, your employees, and your customers? Also, think about how you will transition to the new POS. How does the process of transferring data about customers, products, suppliers, etc. work?

Note that you don’t have to do all the testing yourself. Consider other people who’ll be using the software (cashiers, managers, bookkeepers) and let them take it for a spin as well.

As you’re trialing the software, have the following questions in mind:

Is it easy to learn and use?

Many retail businesses have high turnover rates, so you’re going to want to make sure that you have a system in place that employees can catch onto quickly.

Let a couple of your employees try it out and ask for feedback on how they feel about it.

Are they really my best option or do they just have the cheapest price?

It’s completely understood that you want to save as much money as you can. But please don’t make the mistake of choosing the vendor that simply offers the cheapest bundle.

Go with the system that you’ll get the most value for your buck. For example, POS system A may be cheap, but offers little customer support and limited functionality. POS system B on the other hand, may cost a bit more, but offers a whole range of features (e.g. inventory management, reporting, ecommerce) that will save your business time and money in the long run.

In this scenario, you should go for the second option, because it will likely give you more bang for your buck.

Is it fast?

Anyone that’s ever worked a register knows about that awkward time frame where it takes the system a couple seconds to process a credit card’s payment.

…but what if it ends up being minutes instead of seconds?  

Make sure to pay close attention to how fast it gets things done during your trial or demo.

Does it meet all “must have” and “nice to have” requirements?

Go back to the needs you identified at the beginning of the process and see if the POS software ticks the right boxes. If not, you can either come up with a workaround or choose a different system altogether.

How’s their customer support?

Don’t forget to ask questions regarding their customer support like. Do they offer 24/7 support? What support channels (i.e. phone, email, chat) do they offer? Go with a company whose support offerings match your needs and technical skills.

What’s on their roadmap?

Ask about the features and capabilities that the company has in the pipeline. What’s their “vision” for the future and does it align with your own business roadmap?

Step 6 – Set up: How do you get your POS up and running?

Now that you’ve made your decision, it’s time to get everything up and running for your business. When setting up your POS system, you generally have two options: do it yourself or get a pro to do it for you.

The right answer depends on your business and processes.

If you have a small store, simple workflows, and don’t require a lot of integrations, then the DIY route could be a good way to go. Just be sure to have your manual and any help documents (online or otherwise) handy. It’s also best to chat with your provider’s support team so they can help you with the process.

On the other hand, if you’re running a more complex operation — say you have multiple stores or need to integrate with other retail software — then you might be better off seeking help from a pro.

Ask your POS software provider if they in-house experts who can handle your setup needs. Some solutions also work with third party experts, so you may want to check if there are any professionals in your area who specialize in your POS system.

Step 7 – Get the most out of it: What else can your POS software do?

You’re well aware that your software can read credit cards and print receipts, but what else is it capable of?

Many POS solutions come with employee management tools, inventory management, sales data, customer management tools, etc. You’ll want to go down the list of your new POS software’s features to make sure that you are making the most of it.

Your POS provider should have gone over what they provide, but if they haven’t, don’t hesitate to pick up the phone and ask about any tricks that you may not have been aware of.

Also, don’t forget to keep track of your hardware’s performance and to be aware of any updates or apps that could improve its operation.

You’re all set! (Well, almost..)

Give yourself (and your staff) a round of applause for going through the troubles of finding the perfect POS solution for your business needs.

As time passes, make sure to check in with your team to see how everyone is adjusting to the new system. Consider asking for feedback/questions at the 3rd and 9th week mark after getting your software installed.

Also make sure to have the customer support number written clearly near the register so your employees know how to contact them while you’re gone.

Final words

It’s time for retailers to move on from doing things the “old fashioned way,” especially in today’s world of Yelp and Google reviews where customers are put off by the slightest inconveniences.

Adopting a new POS software for your retail store(s) is one of the most important steps you can take to modernize your business.

If you’re in the process of doing so (and you probably are, if you’re reading this), then we hope this guide helps you find the best POS for your business.

Good luck!

Further reading

If you need a more in-depth reading on how to choose a POS system, check out 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 find and vet providers
  • How to get the most out of the solution

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+.

One Response - Add Comment