Checkout POS Review

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Date Established
New York, NY


Checkout is a comprehensive point of sale system that runs on any Macintosh computer with Mac OS X 10.6 or later. This company makes no secret of the fact that they are catering to the Apple crowd. Their tagline is the not-so-subtle: Point of Sale for the Mac. In general, checkout does a stellar job of aligning itself with Mac branding—the fonts, color schemes, and even the loading pinwheel look the same. When I opened the demo software I felt like I was browsing iTunes–or what iTunes would look like if it had somehow morphed into a point of sale system. Fortunately, Checkout does more than just look great, it’s a decent piece of software as well.

Checkout was developed as an offshoot of a software development company called Acclivity in 2008. It focuses on a few core aspects of point of sale—checkout (I should hope so), inventory, customer data, and reports—and covers those areas decently. However, many other POS systems are broadening their scope to include marketing, which Checkout doesn’t even touch except in terms of customer data collection. There are zero options for gift cards, discount coupons, and social media integration. Those are some small holes that will get bigger as competing software matures. Also, as a local server-based software, Checkout is not cloud/mobile-friendly, which may slow it down in a POS arms race that is increasingly trending towards mobility, constant access, and 24/7 management from anywhere with an internet connection. I have thoroughly tested Checkout and if you read on you’ll find out what I have discovered.

Don’t have time to read an entire review? Take a look at our top rated Point of Sale solutions for a few quick recommendations. Every option we present here offers excellent customer support, detailed user interfaces, and easy-to-use software, all for a reasonable price.


Checkout offers a fantastic 30-day trial that doesn’t require a credit card; I highly recommend checking out this option. Since the software is actually installed on your computer, Checkout charges by license per workstation (i.e. computer). Each license costs $499, and you can connect up to 20 workstations on one local network.

Cloud-Based or Locally-Installed:

Checkout software is downloaded and locally installed onto your computer’s hard drive.

Specific Industry:

Checkout is intended for retail and some types of service industry businesses. It’s not really designed for formal foodservice operations such as restaurants, cafes, or bars. That being said, casual shops like bakeries, delis, or wineries might be able to customize the system to fit their needs. Checkout is great for traditional retail environments though (shoe stores, bookshops, clothing boutiques, jewelry studios, and hardware stores to name just a few). Businesses that incorporate services (as opposed to products) will also find a lot of value in Checkout as it boasts robust invoice, quote, and multiple payment features.

Specific Size of Business:

Checkout is best matched to small or medium sized businesses. A bigger business would be better off using software designed for larger enterprises.

Ease of Use:

Checkout Review

  • Set Up – Installing Checkout is a piece of cake; once I got my bearings I found it to be a user friendly software as well.
  • Point of Sale – A product called “Checkout” better have a darn good checkout interface, and thankfully this software represents its namesake pretty well. Depending on your needs, you can use the checkout feature to process sales, quotes, and orders. You can also convert a sale into an order and vice versa. Everything else about the checkout process is pretty straightforward and easy to understand: multiple tenders, drag-and-drop products, SKU lookups, barcode scanning, notes, history, receipt printing, etc are just a few of the features offered by Checkout.
  • Inventory Management – Checkout really walks users through product management and offers inventory functions that are well designed and user friendly. You can search for any product with a name, barcode, tag, or product ID; once you’ve found the product you’re looking for, you can browse through tabs to edit its price, tax, tags, image, and weight. After you’ve finished managing your inventory, you can head over to the reporting department to keep tabs on a wide variety of items: performance by brand, discounts given, count sheets, and customers to name a few. The reporting options are diverse and simple to use as well.

Hardware and Software Requirements:

You don’t need much to run Checkout. The system requirements are a Macintosh computer with Mac OS X 10.6 or later. Checkout recommends an Intel-based Mac with at least 1GB of RAM. Since your entire system is stored on your computer, you’ll definitely want to invest in some sort of backup storage as well.

Beyond the Mac computer, you can get your POS hardware directly from Checkout or you can put together your own setup. I’ll list the hardware compatible with Checkout below, but note that these are only the products that have been tested with the software, meaning that other brands may also work.

  • Cash Drawer
    • Star CB models
    • APG Vassario BG and BL models

(You can use most cash drawers as long as they have an RJ11 connector and are able to connect to a supported receipt printer.)

  • Receipt Printer
    • Star TSP models
  • Bar Code Scanner
    • Symbol LS models
    • Metrologic Voyager models
    • HandHeld 3820

(You can also use any keyboard that has an emulating USB barcode scanner and can send a carriage return after each scan.)

  • Wi-Fi Router
    • Apple AirPort Extreme
  • Credit Card Swipe Readers
    • If you need to process credit card payments, compatible swipe readers can be obtained by calling Account Edge Customer Care 800-322-6962 or can be purchased online.

(Checkout is not able to process debit cards.)

Product Features:

You can see Checkout’s full feature list here, but I’m just going to cover a few of the features that make Checkout stand out.

  • Order and Invoice Functions – First of all, the order and invoice functions are far more developed than any POS I’ve reviewed before. With most POS systems, a sale is a sale is a sale. But Checkout allows you to sell products, create orders with corresponding invoices, design quotes, require a deposit, and allocate partial payments. You can also easily track the status of all of your orders in the order review area. A yellow warning symbol pops up next to all unpaid invoices. I was impressed with the invoicing capabilities.

Checkout Review

  • Purchase Orders – Checkout’s purchase order feature is well designed. You can create a purchase order from your database of suppliers. Every product is assigned to a supplier, and Checkout has a handy feature that allows you to only view products that are low in stock. With low quantity items isolated, it’s easy to quickly add them to a product order instead of scrolling through hundreds of items. Like the sales orders, you can track a product order’s notes and history, including whether or not items have been received. Checkout does not have any advanced tracking features for purchase order statuses (i.e. order received, in transit, partial delivery), which would be a nice addition.

Checkout Review

  • Management Functions – Other small management features I like are:
    • Notes – You can enable notes on any order to keep track of client requests or changes. The note log tracks when a note was written and who it was written by.
    • History Tracking – Each order has a history log, which records every event related to the order: items added or deleted, invoice assigned, payments made, etc.
    • Shipping Fees –You can assign a flat shipping cost to any custom order, the fee is designed so that it will not affect the tax totals on the order. Granted, the shipping feature isn’t all that advanced, but it is a nice tool to have if your shop ships out the occasional order.

Checkout Review

Integrations and Add-Ons:

Checkout can currently be integrated with three different programs. Checkout additionally offers some free templates and reports that can be downloaded including items such as packing slips and receipts with space for gratuity.

  • QuickBooks – Checkout can be directly integrated with QuickBooks accounting software. Please note that Checkout is only known to be compatible with the U.S. version of QuickBooks.
  • Account Edge – Also developed by Acclivity, Account Edge integrates with Checkout and is a great accounting program. Account Edge itself integrates with Acclivity’s Time Tracker, which is software that can handle employee timesheets for an additional fee. (Checkout only integrates with the Pro and Basic versions of Account Edge)
  • Shopify –  If you’re looking to dip your toes into the proverbial waters of eCommerce, then Shopify may be just what you’re looking for. Establish a Checkout and Shopify account and sync them up by purchasing a $10 dollar a month Shopify connector. Shopify offers a 14 day free trial for you to test this option out.


Compatible Credit Card Processors:

Checkout requires you to process payments through their affiliate merchant account (Forte for U.S. customers and NXGEN Canada for Canadian customers). You can read a decent credit card FAQ breakdown here. I don’t like it when POS developers limit your options to one merchant account because then you can’t shop around for the best rate. Checkout doesn’t exactly have a stellar deal on credit card processing either. Although the processing rates are average (1.79% for card present, 2.29% for key entered), you’re also looking at a $15 monthly fee, a whopping $0.25 per card transaction fee, and a $99 “application fee.”

Sorry, Checkout, not impressed!

Customer Service and Technical Support:

I found little feedback from customers regarding technical support, but here is a list of the different resources Checkout offers their clients:

  • Checkout Support Plan, $99/yr. – Checkout charges a yearly subscription for phone support, but email support is free, and you don’t have to purchase support if you don’t want to. With the other free support options available, it may not even be necessary.
  • Checkout Knowledge Base – As with most POS systems, Checkout features a knowledge base with an extensive series of help articles that should be able to address most concerns is you prefer to troubleshoot yourself.
  • Checkout Forum – Checkout has a user forum, which I always like to see. It seems pretty active with a lot of staff commentary. However, forum topics are broken down into only two categories: Product Questions and Trial Version Questions. You’ll have to do a bit if looking for a specific type of question.
  • Checkout Manual – Sit down with the Checkout manual whenever you’re in the mood for a bit of light reading. It’s got a lot of good information.
  • Checkout YouTube Channel – Checkout has a handful of short instructional YouTube videos that may be helpful.
  • Quicktips – Run through the “Quicktour” videos for another batch of guidelines on basic tasks within Checkout.
  • Blog – Checkout has a blog, but it mostly seems to have detailed breakdowns of what is included in each software update.
  • Facebook – I’m assuming this page was only set up so that the Checkout developers can say, “We have a Facebook!” because there hasn’t been a single post since 2013.
  • Twitter – Checkout also has Twitter, but it serves little function other than to announce recent customers and product updates. In fact, since a post on August 24th, there haven’t been any updates since 2014.

Negative Reviews and Complaints:

I spent a lot of time testing Checkout in addition to combing through online forums and article comments for user feedback. It was difficult to dig up any comments at all since the version 4 update in 2014. This could mean that there have been few issues or it could speak to how Checkout seems to be quickly falling off the map (fewer users, fewer comments). In any case, below are some of my own concerns as well as frustrations voiced by others.

  • High Cost – Checkout charges $499 for each license workstation. If you only need one workstation, then it works out to about $41/month for the first year, which is on par with other POS systems. Obviously, the longer you use Checkout the more value you get out of the initial licensing fee. However, if you have multiple workstations the costs take longer work out. You also have to take into account the support/update fees ($99/year), the merchant account fee ($15/month) and the high transaction fees ($0.25 per transaction—which translates to $50/month with just 200 transactions). I’m not going to say that Checkout is the most expensive POS system out there, but it’s certainly not the cheapest.
  • Issues with Support – Though I found few complaints about support, I didn’t find any positive review of the customer service (even in the testimonials featured on Checkout’s website) so I think it’s at least worth mentioning. Here is what one user said:

“The elusive support team lacks of two basic vectors: The right information and the proper use of English.”

  • Lack of Basic Features – As the customer above states, Checkout is a shallow piece of software. With no gift card options, no social media integration, and minimal discount functions, Checkout has received quite a bit of flack for its limited capabilities. There is no way to scan in coupons, generate time-based or quantity-based discounts, and for service-based businesses, no gratuity features. There were also several user requests for an iPad application.

Positive Reviews and Testimonials:

Aside from the testimonials on Checkout’s website, I was only able to find a couple positive comments about Checkout. Most of them carried the same sentiments:

“Excellent piece of software. No headaches. Easy to use. You do not need more for your little shop.”

More specific positive responses concerned the following:

  • Easy Setup – Many Checkout customers reported that the software was easy to setup and learn. A shop can literally be set up in a day. Clients used words like “easy,” “intuitive,” and “flexible.”
  • Solid Features – While Checkout may not have some of the newer marketing features that other POS interfaces are beginning to support, it does do a great job with what it has. The checkout, stock room and reporting functions do exactly what they’re supposed to.
  • Automatic Backups – As a precaution, Checkout has recently made it possible to schedule up to six automatic backups a day. The files in each backup are compressed into a zipped file for more optimal storage.

Final Verdict:

I really wanted to like Checkout. I really did. I was attracted to the idea that you can just download the software to your laptop and be open for business. I opened the demo thinking I was going to be a fan, and my initial response was good. Unfortunately, my doubts started increasing as I dug deeper. By the end of my review I realized I probably wouldn’t consider Checkout for my own business. It’s not that it’s poor software—it truly has a lot going for it. It’s just that, for the price, I’d rather go with a POS system that has better stability, support, and more marketing options. Gift cards, discount coupons, and some basic social media integration aren’t too much to ask for in 2016. I’m surprised that software that has been around for more than seven years is still lacking these options.

Lastly, I have to point out my concern at the lack of an Internet presence. Aside from the occasional press release announcing a recent software upgrade (the last one issued in 2012) or a tweet about a Boston merchant who is now using Checkout, the software seems to have lost its following (assuming it ever had one). Checkout certainly isn’t making any waves, and doesn’t seem to be making any serious steps toward becoming a competitive POS system. With this little forward movement, I can’t foresee Checkout addressing many of the holes that are going to make it increasingly difficult for its users to function in a constantly expanding market.

If you have a small business that doesn’t need a lot of marketing bells and whistles and you’re willing to pay the Checkout fees, then this Mac-friendly software might be a good option for you. However if your needs don’t fall into these categories I’d recommend continuing your search.


Elizabeth Cranston

Elizabeth Cranston

Writer and Reviewer of Point of Sale Software at Merchant Maverick
Elizabeth Cranston is a writer and native Oregonian who lives in the beautiful Pacific Northwest. She enjoys researching and getting to the bottom of questions relating to the Point of Sale industry.When not writing about and researching Point of Sale software, she can usually be found overindulging in Dutch Bro's coffee, making others laugh, or listening to music.
Elizabeth Cranston
Leave a comment



    Nice read but quite negative, i’ve been running it for about 5 years.Its really quite cheap since you don’t really need to purchase a support contract.Also selling on Enstore is free, merchant account fee ? I have never seen that.Transaction fee ? there is none, all you transaction costs are with paypall or others?Also there is a new version out with shopify integration.Its running really fast for me but if you want the best then do buy a fast touch screen ( like an elo 24 inch) Also use a mac or mac mini in its fastest form with ssd drive. It’s true that there is no gift card option yet. I think that will come soon though.


    This comment refers to an earlier version of this review and may be outdated.


    Ok,I wrote the above in 2014, seems there is no public user support forum anymore. You cannot post to the user base anymore. Also I remember a while back that all important developers on the last version aren’t working there anymore. I’m still using it and was about to get a second license but now they ‘killed’ the support forum it looks i’m going to vote with my feet sooner then later. Anyone knows a good and cheap POS with easy word press shop syncing ?


    All are good except1. U can not give discount on sales price. U can only give on percentage and not amount2. U can not type in sales price including gst(tax)


    This comment refers to an earlier version of this review and may be outdated.


    MAGGIE 732-963-9062

    This comment refers to an earlier version of this review and may be outdated.

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