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Selecting the Right POS System for Your Store

Maybe you’ve grown tired of doing mental math with a green, transparent visor. Maybe you’ve had an over the counter cash register for years. It’s served you well, but you’re curious what else is out there.

Maybe you’re ready to throw your old cash register against the wall, but what comes next? What should you look for? Where do you even begin?

POS system

Lately, at The Grommet Wholesale, we’ve been dogfooding, a grizzly term for using your own product as a customer. We’re using our own site setting up our own popup store on Boston’s City Hall Plaza.

Every day we work with dozens of different retailers across the country and although some of us have worked for larger retailers in our past life, we’d never been through the process of becoming a store owner.

Whether it’s ordering your inventory, processing credit cards or finding just the right fixture for your store, picking your Point of Sale system, is one of the most crucial decisions you’ll have to make with your store. It serves as the hub of your entire business.

We were glad to go through the entire process. Eat the dog food, so to speak. So far, we’ve learned a lot, including countless ways we can improve our own site to make it better for all our Retailers.

POS systems make you more efficient so it’s crucial to fully evaluate your options. Leverage free trials to gauge their efficacy and make sure you or your salesperson ask a lot of questions. Here are the questions we asked ourselves.


  1. Do I need a flexible, cloud-based system or a local one?

Do you do any pop-up stores or have any sales events outside of your store? If so, lugging around a PC, cash drawer, barcode scanner, and credit card swiper may not be the best option.

Square, Vend, and PayPal all have mobile solutions and more are launching every year. If you find yourself venturing out of the store, explore a system with a mobile component.

Such a system will likely be cloud-based. If you’re skeptical of the ever-mysterious cloud and having all your data online, you’ll have to have everything on site. While this increases data security, if the system breaks or the building burns down, everything could be lost. Better be up to date on your backups! Weigh the pros and cons for your situation. For us, a mobile component was essential because of the ability to manage everything remotely and add registers quickly since we don’t know what to expect in terms of traffic.

  1. Does the system work for me out of the box?

Say you find a great system with everything you want, from employee time-tracking to detailed receipts even customizable options. But, it’s a system designed for restaurants. If you have to do a lot of work to make it work for you, you’re better off looking somewhere else. If the system gets updated, it may break what you’ve pieced together.

You also need to think about how well it works with your existing systems. Does it export to your accounting software? Does it work with your ecommerce software? Does it replace them? You want something that isn’t going to constantly give you headaches. We needed a system without a lot of bells and whistles, but could track our inventory, manage employee timecards, and had a quick interface to get customers in and out quickly.

  1. How well does it tell me what I need to know?

If you’ve never had a system that can present sales reports to you, we encourage you to find one because they can significantly improve your business. Ask yourself, am I able to see the strongest salespeople in the store? Can I see which SKUs are moving the fastest? What about which days I’m over- or understaffed and need to adjust employee hours?

What do you want to know about your business? What data do you wish you had today? Can this new system tell you that? Run some test orders through the system and see what data about your store you can discover and thus make you a better storeowner.

We didn’t need any reports that were too unusual, but we wanted the ability to see top performing SKUs at a glance, staffing information, and also track customer sales to facilitate returns and introduce new customers to our ecommerce site.

  1. What happens next?

Systems change, companies go out of business, hardware evolves. How flexible is the system? Can it handle chip cards? Apple Pay? Both have been in use for over a year. Is your software ready to accommodate them? If not, did you know you’re liable for credit card chargebacks due to fraud?

Ensure the system is updated frequently. Is there an app store where new functionality is regularly added? Is that store a stable company or the new kid on the block? If it’s new, are you confident the company won’t go out of business and leave you in the lurch? Is it easy to add new registers?

If your business spikes in December, can you easily add a new iPad and start checking out twice the number of customers in the same amount of time?


We know, there’s a lot of questions you’ll need to ask yourself when starting this process, and ultimately it will be up to you to find the best solution.

If you’re curious, we looked at Toast, Square, Vend, and Shopify. In the end, the ability to add terminals quickly, process Apple Pay, and manage everything remotely led us to Square. If you’re curious about how it’s working for us, stop by our chalet at Boston’s City Hall Plaza Winter, open through the month of December.


  • nick redfield Says:

    Hi Ian,

    Can you send a list or comparison of as many POS as possible?

    Best, Nick

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