Checkout POS Review

  • Updated on:

Need Help Choosing?

Click Here

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. Checkout 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 Mac. 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 it would look like if it had somehow morphed into a point of sale system. Additionally, Checkout does more than just look great. It’s a decent piece of software with a long development history.

Checkout is one of the offshoots of a software development company called Acclivity, itself an offshoot of another company. Acclivity’s founders Tom Nash and Scott Davisson used to work in the US distribution department for a large Australian company called MYOB (Mind Your Own Business). In 2005, Nash and Davisson started Acclivity and bought out the U.S. distribution portion of MYOB. In 2008, they took it a step further and bought the entire US development division as well. With both development and distribution in their pocket, Nash and Davisson started cranking out all kinds of software, including Checkout.

Checkout is Acclivity’s point of sale software, but it’s by no means an only child. The Acclivity family is large and includes AccountEdge (the Acclivity development on MYOB accounting software), AccountEdge Mobile, Time Tracker (an employee timesheet management software), Rerun (a management application for recurring payments), and Enstore (a basic online shopping cart). What’s really cool about using Checkout is that you have a lot of potential integration possibilities with other Acclivity tools if you choose to take advantage of them. For example, you could get your Checkout POS set up and then export all the product and inventory data to your synchronized online store through Enstore. Checkout also directly integrates with AccountEdge, and AccountEdge integrates with Time Tracker. Of course, you have to pay for subscriptions to all these services, but it’s nice to know they’re available should you need them.

Checkout definitely has a more substantial backing than some of the other upstart POS software systems out there multiplying like rabbits. It focuses on a few core aspects of point of sale—checkout, inventory, customer data, and reports—and covers those areas really well. 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. We thoroughly tested Checkout and if you read on you’ll find more info that we discovered.


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 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.

Web-Based or Locally-Installed:

The Checkout software is downloaded and locally installed on your computer’s server.

Specific Industry:

Checkout is intended for retail or some types of service industry businesses. It’s not really tailored for formal foodservice operations like restaurants, cafes or bars, though casual shops like bakeries, delis or wineries might be able to customize it to their needs. Checkout is great for traditional retail environments – shoe stores, bookshops, clothing boutiques, jewelry studios, and hardware stores. 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:

  • Set Up – Overall, I found Checkout to be fairly user friendly once I got my bearings. The install was a piece of cake. I was a bit disoriented with the initial shop screen. Most of the other POS admin menus I’ve tested welcome you to the software with some sort of admin landing page that then allows you to choose what you’d like to manage. Not so with Checkout. It throws you right into the order management page, which is a long list of order data: numbers, addresses, and products. This is really no big deal if you’re expecting it, but I found myself craving the clarity of a landing page (I want my admin welcome page to be a clutter-free Zen garden).
  • Point of Sale – A product called “Checkout” better have a darn good checkout interface, but thankfully, this software represents its namesake pretty well. You can use the checkout to process sales and quotes or orders, depending on your needs, and you can convert a sale to an order or vice versa. Everything else about the checkout process is pretty straightforward and easy: multiple tenders, drag-and-drop products, SKU lookups, barcode scanning, notes, history, receipt printing, etc.
  • Inventory Management – These functions are also well designed and user friendly. Checkout really walks you through product management, which I appreciate. Search for any product based on name, barcode, tag or product ID. Once you’ve got the product you’re looking for, you can browse through tabs to edit pricing, taxes, tags, images and weight. After you’re finished managing 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, among many others. I thought the reporting options were diverse and simple to use.

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 models
  • Receipt Printer
    • Star TSP models
    • Epson models
  • Bar Code Scanner
    • Symbol LS models
    • Metrologic Voyager models
    • HandHeld 3820
  • Wi-Fi Router
    • Apple AirPort Extreme

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.
  • Purchase Orders – After testing Checkout’s purchase order feature, I felt it was also 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 the 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.
  • eCommerce Platforms – One of the most interesting special features is Checkout’s integration with Enstore (the Acclivity web store). Enstore is basic and the Checkout/Enstore alliance is still in beta. The way it works is that all product management is done in Checkout and then streamed to Enstore. Sales from both venues are recorded in the inventory logs, and Enstore meets all basic eCommerce needs such as secure checkout, real-time shipping calculators, and sales tax calculation. However, don’t expect to see more detailed features that many of the major eCommerce providers offer, like robust SEO development, marketing options, and mobile compatibility. To supplement this, Checkout has recently added Shopify to its list of integrations (since most users were underwhelmed by Enstore’s limited capabilities).
  • Management Functions – Other small management features I like are the notes and history function and the shipping fee option.
    • 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 also 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 shipping fee is designed to 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.

Integrations and Add-Ons:

Checkout can currently be integrated with four different programs. See here for more details. Checkout has some additional free templates and reports that can be downloaded as well, 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 – Checkout can also be integrated with its sister accounting program, Account Edge, which is also developed by Acclivity. Account Edge integrates with Acclivity’s Time Tracker, software that handles employee timesheets for an additional fee.
  • Enstore – As mentioned above, Enstore is the Checkout-integrated web store with shared inventory management capabilities.
  • Shopify – A popular eCommerce platform, Shopify is a more robust alternative to Enstore. Though the integrations between Checkout and Shopify may not be as smooth, this eCommerce platform offers more features and customization.

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 (see the “Negative Reviews and Complaints” section for one comment). Otherwise, see below for 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 online forums and article comments for user feedback. It was difficult to dig up any comments at all since the version 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 checkout software runs shallow in the following areas: it restricts the ability to erase, delete or make changes in the invoicing process. For two weeks it kept on adding erroneous data to the database and thus became a chaos. 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.
  • eCommerce Applications – I was originally planning to list this feature in the “Positive Reviews and Testimonials” section below, but after reading the customer responses, I’m going to have to change my opinion. The only mentions of Enstore I found were to say that it was so basic users were switching to Shopify, but even Shopify users are not satisfied. The following comment basically represents what most customers are saying:

“We started with Checkout and was excited when Acclivity announced the addition of Shopify . . . this connector was ok initially, however it will no longer upload product photos and item stock with variations are intermittently updated to correctly reflect inventory. We are a mom & pop shop and we don’t have the time to constantly police what works and what doesn’t. We can’t rely on the software to work seamlessly for us. We have since paused our store on Shopify as we cannot trust the app to update successfully. We are currently looking into dropping Checkout completely and moving to LightSpeed. Although Acclivity staff has been extremely helpful in trying to diagnose and solve the issue, the technology has fallen short and is behind these fast moving internet based times.” –Cowboy Town Tack Western Outfitters

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. The core features are strong and there are a couple of twists I haven’t seen elsewhere (i.e. invoicing capabilities and direct web store integration). 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 2015. I’m surprised that software that has been around for more than seven years is still lacking these options.

Checkout does have some good integrations, but even there I have some doubts. Although the Checkout/Enstore integration is a great concept, I’d probably want to house my website on a better-developed eCommerce platform. However, from the response to the Checkout/Shopify integration, I’m not even convinced that would remedy the problem.

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). Even on Google News, the latest mention of the company was an article written in 2010 about the POS system’s expansion into Australia. Checkout certainly isn’t making any waves, and considering the Enstore/Checkout integration is still in Beta (after more than three years), I can’t see how Checkout is 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.

Jordan Nelson

Jordan Nelson

Jordan is a writer and aspiring editor from a quaint little town just south of Portland, Oregon. She has been publishing her works for just over two years and is constantly expanding her portfolio. When not writing the next great American novel, Jordan can be found lusting after a condo on the East coast, spinning in her swivel chair, and downloading movie soundtracks on iTunes.
Jordan Nelson

Latest posts by Jordan Nelson (see all)

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.


    All are good except

    1. U can not give discount on sales price. U can only give on percentage and not amount

    2. 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

    RatingNot Rated

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

Leave a Reply


Comment moderation is enabled. Your comment may take some time to appear.
Please read the "User Review and Comment Policy" before posting.