Heartland Retail vs. Square Retail: Which is right for you? (2022)

Looking for Point of Sale software? Here's how Heartland Retail and Square Retail stack up.

Heartland Retail vs. Square Retail: Which is right for you? (1)

Mark Hammersley

Last updated 2o October 2020

Heartland Retail vs. Square Retail: Which is right for you? (2)

Heartland Retail

3.9 Stackupp rating

Get started Heartland Retail review

Pricing from

$ 80.00 / month

Free Plan?


Best for

retailers of all sizes. A number of packages which cater to different business needs are available.

Heartland Retail vs. Square Retail: Which is right for you? (3)

Square Retail

3.8 Stackupp rating

Get started Square Retail review

Pricing from

$ 60.00 / month

Free Plan?


Best for

small and medium-sized businesses that are looking for an intuitive interface and a straightforward pricing model.

Heartland Retail or Square Retail: Which is best?

Can't decide between Heartland Retail and Square Retail?

(Video) Heartland Retail Demo

Find the best platform for you with our side by side comparison of Heartland Retail and Square Retail. See how each platform stacks up across ease of use, features, integrations, support and value for money.

Let the comparison begin. Don't worry, we'll guide you.

Is Heartland Retail right for you?

Heartland Retail is a comprehensive point-of-sale system that is suitable for retailers of all sizes, with cost-effective plans for smaller companies and custom packages for larger enterprises. Custom plans come with an array of high-level features like custom user interface branding, training accounts, and location access controls.

Heartland also puts a lot of emphasis on metrics. It has one of the most in-depth analytics platforms we’ve seen in a point-of-sale system, with real-time data and daily summaries.

Users can also take advantage of robust inventory management and customer relationship management tools, along with a dedicated package of features for retail buyers.

On the negative side, the integrations library is a little sparse and payment processing costs are worked out on a per-user basis.


  • Excellent reporting tools.
  • Feature-rich, robust POS system.
  • Suitable for retailers of all sizes.


  • Limited integrations library.
  • A little pricey when compared to other options on the market.
  • Some features are only available on the higher-tier or custom plans.

you’re looking for a feature-rich, comprehensive point-of-sale solution, irrespective of the size of your business. In particular, users that are eager to take advantage of in-depth reporting functionality will find a lot to like in Heartland POS.

Is Square Retail right for you?

Square for Retail is Square’s dedicated point of sale system (POS) for brick-and-mortar retailers. It is offered alongside several other solutions, including Square for Restaurants and Square Appointments (for appointment-based service businesses). This review will focus on the retail option.

Square for Retail has everything you would expect from a point of sale system, including built-in payment processing, integrations with ecommerce platforms, inventory management, a good (if slightly expensive) selection of hardware options, and a fairly comprehensive analytics dashboard.

Notably, Square offers what is perhaps one of the best free plans on the market, although users will have to pay for hardware and the ability to add additional team members at $35 per location.

Square’s fee structure is also relatively straightforward. If you’re not on the free plan, you will pay $60 for each location (with unlimited staff numbers and permissions) and a transaction fee of 2.5% plus ten cents. This is very competitive when compared to other processors, although you will pay slightly more on the free plan. If you run a larger store, with sales above $250,000 annually, you qualify for a custom pricing package.

On the negative side, we would have liked to have seen more third-party integrations, cheaper hardware (many competitor plans include a free card reader), and deeper levels of functionality in some areas.

All in all, however, Square offers an inexpensive and easy-to-use system for small and medium retailers that don’t want the hassle of having to navigate a more complex app. There is also the option to integrate with Square’s ecommerce platform if you don’t already have an online store.


  • Easy and straightforward to use.
  • Transparent pricing structure.
  • Excellent free plan.


  • Lack of integrations.
  • Expensive hardware.
  • Limited functionality in some areas.

you’re a small or medium-sized retailer looking for a solution that won’t require large amounts of time and resources to set up. You just need to be wary of purchasing Square’s complete hardware package, which costs $799.

Ease of Use

Our first comparison criteria, ease of use. Why? Because it’s the most important.

Think about it. You don’t want to invest a lot of your precious time setting up an online store and tweaking the design only to find out that it’s a pain in the butt to manage day to day.

We take a look at how simple the Heartland Retail and Square Retail platforms are to run.

How easy is Heartland Retail to use?

Rated 4/5 for Ease of Use

While the Heartland Retail user interface isn’t the most intuitive we’ve come across, it isn’t difficult-to-use by any means. The main POS dashboard is accessed via an iPad or Android app or via a browser (if you want to use a desktop computer to run your POS).

Both the tablet and desktop interfaces follow a fairly typical design. A top-of-the-screen menu links to dedicated areas for processing sales and payments, reporting, inventory management, customer relationship management, employee permissions, and so on.

Keep in mind that Heartland is best-suited to an iPad or Android tablet set-up. Alternatively, you can run the software using a computer browser. At the time of writing, we are not aware of an offline mode.

What Heartland Retail customers are saying...

"It's mobile and in the cloud so we have access anywhere and anytime."
"Reports are entirely customizable and there are several metrics to choose from."
"It's easy for my seasonal employees to use, but not remarkably more or less than any other POS."

How easy is Square Retail to use?

Rated 5/5 for Ease of Use

Square for Retail is very easy to use. Everything from the back-office dashboard to the “smart” store builder is designed to streamline the process of taking and managing payments.

The POS register, which is usually accessed via an iOS tablet or Square’s in-house register, follows a typical block format, with an area that displays individual products and categories, a checkout box, and additional options like discounts, gift cards, popular items, and so on. It’s also possible to use your tablet to receive tips, send email receipts, check inventory at different locations, and so on.

The back-office is also designed in a traditional way, with a left-hand sidebar providing access to dedicated areas for managing sales, analytics and tracking, employee permissions, and more.

(Video) How to ring up a customer on Heartland Retail POS | The Style Shop

What Square Retail customers are saying...

“Square is a great product that is a wonderful tool for small businesses and nonprofits like ours.
“It operates just like your mind works. It is so logical.”
“I liked that it was a convenient way to accept payments anywhere via my mobile cell phone through the Square App.”

Square Retail is our winner for ease of use

Heartland Retail Features

Rated 4.5/5 for Features

Heartland doesn’t disappoint when it comes to features. It definitely ranks as one of the most feature-rich platforms we’ve reviewed, especially on the analytics and reporting front. It is recommended that Heartland be used with an iPad, but it’s also possible to run the software on an Android tablet (depending on the software version) or through a browser on a desktop computer.

Retailers will have access to an array of tools for managing inventory, organizing vendors and retail buyers, running advanced reports, storing customer details, setting employee permissions, and more.

In regards to the POS system itself, features include email receipts, gift cards and loyalty program discounts, a customer-facing display, and a mobile app.

Finally, enterprise users have access to price lists and customizable products, purchase order allocation, user interface training, training accounts, and the API.

As a slight negative, it’s also worth pointing out that advanced analytics are not available on the lowest-priced “Plus” plan, although limited reporting functionality is included.

Square Retail Features

Rated 4/5 for Features

Square for Retail has a fairly comprehensive feature-set and comes with everything you would expect from a point-of-sale system. Keep in mind that you will only have access to all features on the $60/month “Plus” package. The free plan provides only limited functionality.

Square back-office is a browser-based app. The register interface is accessed via an iPad or the Square register. Support for Android tablets is not provided, but you can download a feature-limited Android app to take mobile payments.

Checkout features include saved carts, barcode scanning via the iPad camera or Square register, discounts, item searches, and exchanges. Payment functionality, which works on a straightforward, transparent fee structure, comprises next-day transfers, invoices, and both physical and digital gift cards.

You won’t find anything lacking on the inventory management front, either. Tools include unlimited products, low stock alerts, bulk inventory uploads, barcode printing, and more.

If you decide to use Square’s in-house ecommerce solution, you will also have access to a user-friendly store builder, automated inventory syncing, and integration with Instagram.

Finally, analytics reports cover sales, profit margins, vendor sales, and total costs.

Heartland Retail is our winner for features

Heartland Retail Integrations

Rated 3/5 for Integrations

When it comes to integrations, Heartland doesn’t perform as well as some other solutions we reviewed. The integrations library isn’t terrible, but there could be a lot more on offer. What’s more, use of some integrations incurs extra costs.
We would like to point out, however, that if you are happy with the broader feature-set of the POS solution and the integrations library does meet your needs, then the limited number of options to sync with third-party apps is unlikely to be an issue. Judging from user reviews, Heartland also seems very responsive to requests for new integrations.

On the ecommerce front, BigCommerce, Shopify, Magento, and WooCommerce are all supported. Sales integrations include Salesforce, Mailchimp, and Annex Cloud. The main accounting integrations are Quickbooks and Oracle Netsuite. Unfortunately, a connector for Xero isn’t provided.

Another downside with the integrations library is that Heartland isn’t compatible with any “intermediary apps” like Zapier or Kosmos which would provide access to a large range of third-party tools.

Square Retail Integrations

Rated 2.5/5 for Integrations

Integrations represent one area where Square could have performed better. If you’re looking for a POS system that syncs up seamlessly with your existing tech stack, you may be forced to look elsewhere. That said, Square does provide a small package of integrations, so you may find what you’re looking for. A Zapier integration is also available, so you can sync up with most apps, albeit with limited functionality.

Square performs best in the area of accounting and tax, where a large selection of integrations is offered, including Quickbooks, Xero, Shogo, Kahoo, OneUp, ZohoBooks, and more. A small number of connectors with analytics, team management, and restaurant apps are provided.

Square’s online payment processing tool also integrates with most well-known ecommerce platforms like WooCommerce, BigCommerce, Magento, and so on.

Heartland Retail is our winner for integrations

(Video) Heartland Restaurant POS Demo

How much do they cost?

Everyone’s favourite topic - pricing. Let's dive in to see if Heartland Retail or Square Retail offers better value for money.

How much does Heartland Retail cost?

Rated 4/5 for Pricing

A short introduction to pricing ~100 wordsHeartland offers three plans. The “Plus” plan is $80/month per register, the “Professional” plan is $160/month per register, and the “”Enterprise” plan is priced on a custom basis. Heartland stipulates that it integrates with a variety of payment processors but doesn’t publish payment fees on its website, so it’s likely that you will be able to use your preferred payment processor but may have to pay additional fees.

While Heartland isn’t as inexpensive as some other solutions we’ve reviewed, it’s important to keep in mind that users are getting access to a pretty extensive feature-set.

We were also pleased to see that most functionality is available on the entry-level plan, with the exception of API access. If you opt for Heartland, you won’t be compelled to move onto a higher plan because certain essential features are lacking.

How much does Square Retail cost?

Rated 4/5 for Pricing

Square has a straightforward, competitive pricing structure. We consider the free plan to be one of the best available to small and medium retailers. Three plans are offered: “Free”, “Plus”, and “Premium”.

The free plan is ideal for small shops and comes with a limited number of features. If you want to add extra team members, you will have to pay $35/month per store. The “Plus” plan, which most users will opt for, costs $60/month per location and includes the full feature-set and discounted payment processing fees.

Finally, the “Premium” plan, which is geared towards larger enterprises, operates on a custom pricing model and is available to sellers turning over in excess of $250,000 a month.

It's a draw!

Help and Support

If things go wrong (and they often do) you need to know someone’s there to help get you back on track. So, how does Heartland Retail's and Square Retail's support measure up?

How good is Heartland Retail support?

Rated 4/5 for Help and Support

Heartland offers a solid support package with email and live-chat services available on the basic plan from 8 AM to 9 PM EST. The mid-tier plan also includes phone support, and the enterprise plan has an “Elite” customer service package with a faster response time guaranteed.

Onboarding packages are included on all plans with the option to upgrade for more one-on-one time.

How good is Square Retail support?

Rated 3.5/5 for Help and Support

Square customer support is available via phone, email, live chat, and social media. Users also have access to extensive documentation and an active seller community.

User reviews of the quality and speed of support are mixed, with many users talking positively about helpful staff and fast response times but complaining about receiving generic answers.

There are no custom onboarding packages, although the ease of setting up largely removes the need for them.

Heartland Retail is our winner for support

The Bottom Line

The final say. Let's wrap up our thoughts on each platform.

Heartland Retail: Our Verdict

Heartland Retail is one of those rare beasts - a point-of-sale solution that is genuinely suitable for retailers of all sizes, from mom-and-pop stores to enterprise chains.

It has an excellent set of features, one of the best analytics dashboards we’ve seen, and is reasonably priced. While there are cheaper alternatives available, it’s unlikely that you’ll have access to the same number of features.

The support package is also excellent, with onboarding and data-migration options for new users.

(Video) Heartland - Register

The one big downside is the limited integrations library, so be sure to check that you have access to all the connectors you require before subscribing.

Square Retail: Our Verdict

Overall, we were very impressed with Square. It’s one of the easiest-to-use platforms we reviewed, and the “forever free” plan is arguably the best on the market. Small and medium-sized retailers that are looking for a streamlined, straightforward solution with transparent pricing will find a lot to like. The only real downsides are the limited integrations library and the expensive hardware, although this won’t be a problem if you’re using an iPad.

Larger store-owners will likely require more extensive functionality, especially when it comes to analytics and integrations. Nonetheless, it is still worth getting in touch to discuss options if you’re generating sales of over $250,000 per month.

Overall, we found Heartland Retail to be the better Point of Sale platform.

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In this article

(Video) Heartland's Service Solution. Proving Better is Possible and Doing More for our Dealers & Customers

  • Is it right for you
  • How easy is it to use
  • Product features
  • Integrations
  • How much does it cost
  • Help and support
  • The bottom line


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