10 Questions to Ask When Considering a New Retail Point of Sale System

Wednesday, June 29, 2022

The idea of switching your retail POS system can feel like a daunting task. Besides the learning curve, there's the data migration, hardware and training to consider. Not to mention the 20+ options of POS system for retail alone to sift through. How do you determine the right point of sale for your retail business? You’ve likely even asked yourself, is it really worth it?

Let’s face the tough truth: If your current retail POS isn't supporting your enterprise and helping you grow profitably, or if its bulky, slow and/or glitchy nature are keeping you and your staff from staying efficient and delighting customers, then it is definitely worth considering your options to find a POS system that will help your retail store succeed.

Today’s retail POS systems should do far more than just ring up a sale. To stay competitive, you need a powerful and flexible retail management platform, and finding the right fit can make a real difference to your bottom line. Start the search for the best POS system for retail by asking yourself key questions to ensure you are dialed in to your business’s unique needs.

1) Was my POS system designed specifically for retail?

Many POS solutions claim to handle retail, cafés, restaurants, franchises, salons...but the needs of these industries vary greatly. Consider such as you compare platforms; a one-size-fits-all POS system likely lacks the flexibility and customization you as a retailer require. A follow-up question to this: Do I have to alter my desired business operations because of my POS system’s limitations?

2) Can I access my back office from anywhere?

COVID-19 has reaffirmed this: If you have to physically be in the store or log in remotely to access your store's data, it's time for an upgrade. Cloud-based iPad POS software allows you to access your data wherever and whenever you need it: from your home office, warehouse, other store location, on the road or even on vacation! The data should also be available in real time; if you have to wait for a manual sync or download, you're wasting precious hours.

3) Do I have to pay for upgrades?

If you're getting hit with a fee every time you need a system upgrade or maintenance, you need to explore new pricing models. Some POS platforms have low upfront costs but slam you with frequent charges, while others have a slightly higher monthly cost but never charge for software updates. Commit to one that suits your long-term business model.

4) What features are included versus add-ons?

It’s not uncommon to enhance your POS platform’s built-in features with top retail POS technology integrations, be it a powerful loyalty solution or e-mail marketing software. But when you find yourself needing a third-party for inventory, purchase orders, reporting or other critical POS features, you’ll be dealing with many more puzzle pieces that will likely need support or reconnecting over time, if not very frequently.

Apps also drive up the total cost of ownership, and suddenly that cost-efficient solution will be draining your wallet as you strive for the feature parity level of other end-to-end retail management systems.

5)  Can I connect my e-commerce store to my brick and mortar?

Today’s consumers demand a seamless shopping experience: They want to be able to browse, shop, check out and return between all channels without friction. An omnichannel retail POS platform will provide that consistent brand experience while keeping a central record of all inventory, sales and customer data, so you can get a holistic view of your business and reduce manual work.

6) Are my POS reports providing me with enough data to help me make smarter decisions?

Many point of sale platforms come with canned reports, while few others provide you with the flexibility to create custom fields and reports, allowing you to collect the data most relevant to your store, then slice and dice it in any way you choose. What intel do you need for your unique retail business? Daily sales and customer emails aren’t exacting groundbreaking data points that will help you make critical decisions to grow profitably. Customizable dashboards, unlimited custom fields and flexible reporting features? Now those will.

7) Do I need multi-store or omnichannel capabilities?

Even if you’re a small business only operating one location or channel right now, think ahead: Are there others on the horizon? If you already are or plan to become a multi-location retailer, multi-channel capabilities need to be at the top of your list: Multi-channel inventory management, the ability to scale up or down seamlessly, cross-platform accessibility and real-time data stored in the cloud. In short, you need a POS system that allows you to operate your business from anywhere and that can grow alongside you.

8) Does my retail POS help me buy efficiently?

Built-in purchasing and receiving tools enhance productivity and save money on a daily basis, but their value is especially evident as you prepare for buys. The most powerful point of sale systems allow you to build purchase orders from the road, run reports on the fly and use them to negotiate with vendors, and connect your POS with leading ordering platforms to keep things streamlined and reduce extra manual work.

9) How well does my current POS system allow me to enhance my customers’ experience?

Retail trends come and go, but customization (in all its many facets) is here to stay. Customers demand it and expect you to understand and predict their preferences—often before they do. Look for a POS with a built-in CRM, providing you with data-rich customer dashboards, custom fields and integrations with top loyalty and marketing platforms. Having this 360-degree view of your customers—their habits, interests and shopping journey—will allow you to better buy for, market to, engage and retain them.

10) How will I transfer all of my current data to a new POS system?

How complex is your retail data? Do you feel comfortable exporting and importing yourself? Be sure to consider these questions and inquire about your data transfer options when shopping around. Most POS companies will give you the option to import your own via spreadsheets, or request a data migration service. Be wary though: Most companies will outsource migrations, meaning your data will be in a third party’s hands. If you go the hands-off route, confirm that your new POS provider is doing the migration internally.

There’s no denying that shopping for a new POS system for retail is a laborious task, but by asking the right questions, you can narrow the field of contenders. Our retail consultants are focused on connecting you with the best fit for your business, and if that’s not Heartland Retail, we’ll tell you!

For a free consultation—and any other questions you might have—click here.


Heartland helps nearly 1,000,000 entrepreneurs make and move money, manage employees and engage customers with human-centered technology solutions that allow them to rise above the daily grind and lead their businesses into a brighter future. Learn more at heartland.us