Checkout POS Review

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Checkout is a comprehensive point of sale system that runs on any Macintosh computer with Mac OS X 10.5.8 or later. Small to medium sized businesses can use Checkout to process sales, print receipts and invoices, manage inventory, compile reports, and collect customer data. 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 look the same, the colors look the same, and, heck, even the loading pinwheel looks the same. When I opened the demo software I felt like I was browsing through what  iTunes would look like if it had somehow morphed into a point of sale system. 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. Acclivity is an offshoot itself. See, 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). You may have heard of the MYOB accounting software because it’s one of Quickbook’s primary competitors. In fact, Quickbooks and MYOB pretty much dominate the accounting software market. In 2005, Nash and Davisson started Acclivity and bought out the US 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. You’ll 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’s 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 might get bigger as competitor 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. You can use the pros and cons to decide whether or not it might be a good match for your business.


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

Another pricing factor to consider is support, which runs a hefty $30/month for one workstation and another $10 for every additional workstation.

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 something like a bakery, deli or winery might be able to customize it to their needs. Checkout is great for traditional retail environments like shoe stores, book shops, clothing boutiques, jewelry studios, and hardware stores. Businesses that incorporate services (as opposed to products) will also find a lot of value in Checkout, which 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:

Overall, I found Checkout to be fairly user friendly once I got my bearings. The install was a piece of cake. I submitted my contact information and the download link for the demo was immediately emailed to my inbox. A couple of clicks later and I was looking at a demo welcome screen that gave me the option to start a store from scratch, test a pre-built shop, or contact the help desk. I opted to give the pre-built shop a whirl in order to best understand all of its capabilities and functions. 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).

A product called “Checkout” better have a darn good checkout interface and, thankfully, it represents its namesake pretty well. You can use the checkout to process sales, quotes or orders, depending on your needs and you can convert a sale to an order or vice versa. Orders are different from sales in that you can create an unpaid invoice to be delivered to a client, you can assign a deposit and you can allocate funds towards a partial payment. Great features. 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.

The inventory management functions are also well-designed and user friendly. Cruise on over to the “Stock Room” and create a purchase order based on vendor and low-stocked products. Checkout really walks you through product management too, 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 its 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.

Checkout definitely gets good marks for usability.

Hardware and Software Requirements:

You don’t need much to run Checkout. The system requirements are a Macintosh computer with Mac OS X 10.5.8 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 Checkout hardware prices below, but feel free to shop around.

  • Hardware Bundles – Checkout offers two hardware bundles. The Standard Hardware Bundle is $799 and it includes a receipt printer, a cash drawer and a wired bar  code scanner. The Premium Hardware Bundle is $1199 and comes with a receipt printer, pole display, cash drawer and wireless bar code scanner.
  • Cash Drawer – Pickup an APG cash drawer for $159.
  • Printer – Checkout sells a standard Star Micronics thermal printer for $399.
  • Bar Code Scanner – As far as Checkout bar code scanners go, you can choose between a wired Honeywell bar code scanner for $279 or a wireless Bluetooth Argox scanner for $599.
  • Credit Card Reader – Checkout offers a secure MagTek credit card reader for $89.
  • Displays – Not all small business POS softwares are compatible with displays, but Checkout sells both a table top display for $299 and a pole display for $199.

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 unique from other POS softwares. 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. 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.

Other small management features I liked were the notes and history function and the shipping fee option. 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. Each order also has a history log, which records every event related to the order: items added  or deleted, invoice assigned, payments made, etc. When it comes to processing an order Checkout offers a shipping fee option, which is a feature I haven’t seen other POS softwares offer. 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.

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 a supplier’s products that are low in stock. With the 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 (ie. order received, in transit, partial delivery), which would be a nice addition.

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. Checkout differentiates between products sold in the shop and product sold online. Sales from both venues are recorded in the inventory logs. The Enstore integration could be good for shops that only have a few products and want to be able to sell them online as well as in their brick and mortar store. Enstore meets all basic ecommerce needs such as secure checkout, real-time shipping calculators and sales tax calculation, but 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. Despite Enstore’s basic structure, I like the idea of a direct interface between brick and mortar POS and an ecommerce shop because I’m personally familiar with the giant headache of setting up a smooth network between a ecommerce website, a shop, an accounting system, and inventory management software. It often involves a lot of intermediary software and custom coding. Acclivity’s all-in-one approach is pretty clever. If they continue to develop it, they might have a really interesting product to market.

Integrations and Add-Ons:

Checkout can currently be integrated with three different softwares. 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 US version of Quickbooks.
  • Account Edge – Checkout can also be integrated with it’s sister accounting program, Account Edge, which is also developed by Acclivity. Account Edge integrates with Acclivity’s Time Tracker, a software that handles employee timesheets.
  • Enstore – As mentioned above, Enstore is the Checkout-integrated web store with shared inventory management capabilities.

Compatible Credit Card Processors:

Checkout requires you to process payments through their affiliate merchant account (ACH Direct for US 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 always make it a point to test both email and phone support whenever I’m reviewing new software. Checkout didn’t do well on either. According to the demo product guidelines, I’m elegible for 30 days of the same support resources that Checkout support subscribers receive. Full disclosure: I wrote this review over the weekend, so I tested the support options outside of the normal M-F workweek. I’m not sure what their standard support hours are because no one answered my phone call (the automated voicemail just directed me to their DIY support resources online) and my emails went unanswered as well. For me this is a problem. Most businesses are open over the weekend so why should they pay (minimum) $30 a month for slow or unavailable support during the times they are open? I’ll end my rant for now, but you can see the “Negative Reviews and Complaints” section for more of my issues with Checkout’s support structure. See below for the different resources Checkout offers their clients.

  • Checkout support plan (fee-based) – Checkout charges a monthly subscription for support and software updates. Read more about it here. Support is $29.99 for one workstation and $9.99 for every additional workstation.
  • Checkout Forum – Checkout has a user forum, which I always like to see. It seems pretty active with a lot of staff commentary. However it doesn’t have forum topics broken down by category. You’ll have to dig 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 on Youtube – 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.
  • Twitter – Checkout has a Twitter. Here it is.

Negative Reviews and Complaints:

I spent a lot of time testing Checkout in addition to combing online forums and article comments for user feedback. Below are some of my own concerns as well as frustrations voiced by others.

  • Errors/Slow Processing – One of the primary customer complaints was regarding bugs and “known issues” that come up regularly. Some clients report the software crashing mid-transaction while others have had difficulty with lag and slow processing during transactions. Making the customer wait is not a fun retail situation. The demo crashed while during my own test transaction for no apparent reason. A detailed error message appeared and I had to reset the program. Problems with crashing and errors are a huge turnoff for any POS software. If there’s one moment you want to go smoothly it’s the point where the customer hands over their credit card.
  • 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 (minimum $30/month), 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 – I am not thrilled with Checkout’s charge-based support. I understand that since Checkout offers one-time licenses it works best for them to sell support–they can’t incorporate it into the monthly subscription fees like other POS company cost structures can. Still, I don’t like that you have to have pay for an entire support plan to get significant software updates. That seems less than ideal. Plus, the support fees are expensive for a platform directed at small businesses. Checkout’s support fees are $30 for one terminal and another $10 for each additional terminal. Their support fees alone cost as much as the entire monthly subscription fee for other POS providers (support included!). Also, if support is going to be expensive it better be good. Unfortunately my personal experience did not leave me feeling confident in the Checkout customer service department. There are many reviews from frustrated Checkout clients expressing their frustration with Checkout support (or lack of it, rather).

Positive Reviews and Testimonials:

Checkout customers had some positive things to say as well. Most positive reviews focused on ease of use and quick initial setup.

  •  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.

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 a 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 isn’t too much to ask for in 2013. I’m surprised that a software that has been around for more than five 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 if I had anything except a very, very basic setup.

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.

Amad Ebrahimi
Amad has worked in the eCommerce and online marketing world since 2002. He started as an eBay seller, then slowly graduated to building & marketing his own websites and consulting others to do the same. He founded Merchant Maverick out of frustration with all the misinformation and shady tactics that he encountered when trying to find a merchant account for his and his client's businesses. He's the man behind most of the merchant account reviews, and articles posted on Have any questions related to credit card processing? Talk to him.
Amad Ebrahimi
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