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About Windward System Five
Windward System Five is a full business management system for companies that sell, service, or rent inventory.
The cloud-based system is easy to access and use on a daily basis.
Some of the reporting features make getting an accurate snapshot of what is occurring in the company a little difficult.
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Filter reviews (188)

A powerful POS with unlimited flexibility, reliable stability, and great support staff.
Comments: Saved our company time and money in the ling run. Being able to customize the look, feel, and functions of the application let us implement EXACTLY what our company needed. We evaluated MANY other products before choosing Windward, and nothing comes close. It was one of the better decisions made in our organization, and is a big personal red-feather in my hat.
Pros:
- Extremely customizable. Allows you to customize anything from report, to custom price-labels, to customized POS screen (even changing the size/color/look of virtually every button). If you are a little more adventurous, you can even write code that allows you make your own functions. - Easy to learn. For as advanced as this is, most people can pick up on the majority what thy need in a day. For those who want to do more, their is a complete 'Windward Academy' that you can watch videos and read comprehensive guides. - LOTS of support. If I ever have a question, there are about ten people I can call. Of-course, they have 24/7 technical support, but virtually anyone in the company is eager and willing to help. I can call my account manager, or any number of others I have talked to throughout the installation process. Even the lovely receptionist is awesome has walked me through issues on more than one occasion. - Philippines support. You might think this would be under the "Cons" section; but it isn't. The Philippines support is not outsourced like other companies, but they are actual employees working in a Windward office in Cebu. They all speak great English, are EXTREMELY knowledgeable about the product, and aim to please. No matter how frantic I am when I call, they never get upset and are always positive. And they are not going to give up until it's fixed. - You typically don't find this level of customer service in Western support groups.
Cons:
- Price tag will be your biggest hurdle. And some features will cost you extra. Having to pay extra to have the software integrate with our merchant account is probably the biggest complaint I have with the company. But even this is vastly outweighed by the Pros. If you want the best, it probably isn't going to be the cheapest. - There are occasional errors that pop up and random issues. But 90% of these are self-resolving (very intuitive software). For the other 10%, support is right there to remote in and stay with you until it's resolve.
Alternatives Considered:
Great system management
Comments: When we first took over this long-time local business, previous owners did most reports or tracking by hand (ie hand-written invoices entered into QB and hand-written price books) WWS5 helps us keep track of items in inventory, current prices and mark-ups for inventory, general price increases from vendors, EOD reports and sales, and AR accounts much more easily. We do not currently use the accounting portion, but hope to move over to the accounting option with the new data set.
Pros:
We currently use Windward for our POS and AR needs. This helps keep us on track for monthly billing to AR clients and keeps up with the daily till. We do very much like the additional features such as inventory management, price checks/updates, but have trouble at time keeping it current due to staffing issues. With more staff, this system would be absolutely amazing.
Cons:
When we first installed Windward, there were issues with understanding the larger picture during set-up. Understanding more about the system prior to set up would have helped. We are currently setting up a new database now that we understand more about the full operation of WWS5.
Would like to set up the system again knowing so much more now than was first told.
Pros:
Windward is easy to navigate and manipulate. Inventory items are easy to add and change. Like the way the payroll system integrates with Windward so no need to journal . Love the support I have received when requiring assistance from the team in the Philippines . They are prompt in getting back to you and try to assist at all times.
Cons:
When trying to customise the system to suit our requirements alot of manual hours are required to change simple things like updating prices and modifications. When we needed to collect information from the system we required a special programme be written to fulfil government requirements. This additional reporting is cumbersome to produce. There is also alot of double entry when making a payment and then having to do a journal entry to reflect the same. A journal entry should be automatic. Would like the ability to make ledger numbers inactive Although we have a very confusing payroll and tax system, we experienced many issues with setting up the payroll system with this year being the first year we have successfully produced a payroll summary. Even then it required alot of double/triple checking to ensure the information was correct. Adding a new employee is once again difficult and time consuming. It would be great to be able to copy an existing one.
Windward Software Response
6 years ago
Thank you, Michelle, for taking the time to provide a review of your experience with Windward System Five. It's nice to hear that you are pleased with the support you have received from our Client Services team. In terms of your concerns, we're confident that there are means to make some of the processes you mention more efficient. At your convenience, please contact your Account Manager at +1 (800) 663-5750 and ask to be registered for The Windward Learning Academy. This is a user-friendly yet comprehensive online source of System Five tutorials, which provide step-by-step solutions for all product features and nearly all possible scenarios. Windward Software is continuously evolving and enhancing Windward System Five, and, in developing each product release, we examine client feedback to ensure that we are delivering a solution that meets and exceeds needed functionality.
Alternatives Considered:
Windward Software is an amazing program to help you run your business in every aspect.
Comments: Inventory was a huge issue for us before we started using System Five. We absolutely cannot imagine running our business without Windward System Five at this point.
Pros:
The Support is A1 and the features of everything from Inventory to Sales Invoices, everything is connected and very user friendly. Reports are easy to run, reconciliations, sales and purchase invoicing, ageing, financials are easy to read and all other functions are again, user friendly.
Cons:
No cons at this time. We didn't like that it didn't have a payroll feature when we started with it but now it does.
Alternatives Considered:
Windward Review
Comments: Mostly positive when it comes to day to day interaction. Any negatives are more nit-picking issues.
Pros:
Required Orders system and ability to interact with the invoice easily throughout.
Cons:
Lack of multiple kits. Purchase orders with SO items become buggy with large quantities. If a user moves too quickly in the system, it can break.
Stay Away, poor Company and Poor program full of glitches
Comments: spent alot of resources and time to get their web module to sell online and they discontinued it the next year just as inventory came online
Pros:
Windward is just there for your monthly fees, not to support you
Cons:
glitches in the system for inventory control, does not count correctly stock constantly out
Windward Software Response
3 months ago
Hi Anatoly, We're sorry about your experience, but we're having trouble getting ahold of you to to resolve your concerns. Please reach out at [email protected] so that we can discuss.
Tami McQuown
Comments: Its been a great experience!
Pros:
Ease of use, technical support answers all questions
Cons:
Credit card transactions did not go well at first
Gets the job done. Do not do the updates.
Pros:
Very thorough software with lots of room/areas to store Information and very easy to use. The point and click ability of the software makes it easier to train new staff. Can access the software from anywhere in the world using remote desktop connection.
Cons:
The updates do not seem to go very smoothly. And update me fix one problem but two new problems arise that were not problems before. We have actually stopped getting updates and have continued to use our current version for years. We have developed our own internal ways to use the software to its fullest potential without getting updates. Software support is readily available however very expensive and a lot of the problems that we have encountered do not have the solution. In order to get the solution we have to pay for the entire resource development team and have to be very very patient to see results. The yearly license fee does not benefit our company as we do not complete the updates. So we paid the fee however are using an out of date software program Because we are afraid to update. Phoning for tech-support can be quite challenging when the bill is charged per minute and we are on hold for 80 percent of the call. We are usually on hold while the tech support discusses with superior or development team to solve our more complex problems. At the end of the day the software program helps us maintain our current business but is not helping us grow our business. We are not ready to commit thousands of dollars to the software program that still has many issues even if we were to update to most current version

This softwear has made our business extremely essential to operate.
Comments: the main function of our business, our retail set up revolves around the software making it easy to operate day to week, to month to yearly. it has been absolutely essential. recording & keeping track of everything form our substantial amount of inventory, along with accounting, reports, staff, ect. our main source of operations for sure. :)
Pros:
that is is absolutely fluent in keeping all of our information organized & keeps me able to do my job as a 1 woman Owner/Operator. without this softwear we would not have been able to stay open for the past 11 years without the ease of Windward System 5, for my retail business.
Cons:
for us a small retail shop, the maintenance & updating costs are quite high & out of our price range on a year to year basis.
Windward Software Response
6 years ago
Hi Marie, thank you for taking the time to provide feedback relating to your experience with Windward System Five. We're very happy to see that it's significantly helping the operation of your business! With regard to maintenance & updating, please contact your Account Manager at +1 (800) 663-5750, at your convenience, to discuss options to determine the most cost-effective solution. For example, it may be optimal to transfer to Windward System Five on Cloud, which includes automatic data backups and installation of updates and does not require your business to use a server.

I've been a Windward user for close to 20 years. Overall, my experience is frustration.
Comments: The system has a good POS system. It is quite easy to use but does have serious flaws. You can integrate VISA processing with the system, however, this opens another set of problems.
Pros:
The ability to expand on transactions no matter which module you are in is a nice feature. The GST function is also very good.
Cons:
With every update, there is a new set of problems. In addition, you can not add additional data bases, terminals nor change your company information such as address, phone etc. Windward's main goal seems to be collecting licence renewal fees and support fees at higher than market rates. They control the number of users - unlike Simply Accounting who allows up to 10 users for a basic license. Windward also charges a licence fee PER DATA BASE. This is bogus! Overall, I am disenchanted with Windward and moving away from the product after over a decade of use.
Using Windward in a Small Shop
Pros:
Windward offers a comprehensive set of features, more than we will ever use. What drove us to purchase Windward is that its POS features are fully and seamlessly integrated into its accounting software. That means that both our POS and accounting data is up to date and current at all times. No integration with other software is required. Windward does it all. Another thing I like about Windward is the quality of Windward's support. Windward not only sets the system up for you and makes sure that all you point of sale devices work (barcode scanners, printers, etc), but if you are a cloud customer or have a maintenance contract, Windward will also remote in to your machines and fix any issues you may have. In addition, they have an on-line learning academy with training videos, documents, etc. that help you continue to learn the functionality of the system. They also offer live sessions on specific issues like maintaining inventory, year-end procedures, etc. We needed a lot of hand holding when we first started--I had no previous experience with POS software--and Windward successfully guided even a slow learner like me!
Cons:
Windward is continually upgrading its software to provide additional functionality or to streamline its processes. We recently moved to the cloud version of Windward, and that has reduced some administrative overhead for us--no need for backups, no need to install updates, and greater data security. So overall, it's a plus. But there is one feature I miss in the cloud version. When our software was installed on site, we were able to print barcode labels directly from Windward to our barcode printer, a Zebra ZT510. That feature no longer works for us in the cloud, and I'm told that the reason why is that the cloud version of Windward does not currently support our particular printer. I'm still looking for a better answer from Windward. But what that loss of functionality means for me is that I must now create a separate barcode database in Excel, link that database to Zebra's barcode software, and print my barcode labels through it. So you should pay close attention to the particular peripheral hardware that Windward supports.
I wish I never heard of Windward Software
Comments: Our overall experience was extremely poor and detrimental to our business. All our staff were frustrated ( I nearly lost staff), some customers were frustrated, we invested so much money, and have in turn lost so much money. Oh and did I mention the time invested. All that time I spent, all a waste, the time my staff spent which I paid for, such a waste. So much stress that my whole team went through only to end up worse off. Before we went live, in my gut I had doubts due to my experience with Windward staff in the lead up transition period. But unfortunately I have faith in people, and faith that people tell the truth, and they assured me that the Windward System 5 was an investment in my business- to have confidence, to go live and realise the benefit. Oh so wrong. The system just plain and simple had so many glitches and caused more harm than good to my business. Once live, it just got worse and worse. In hindsight, I should have listened to my gut in implementation, written the money invested off as a bad business decision and aborted. By pushing on, I cost my business so much more, and then blindly I stayed for the full 60 days as required by the refund clause, further harming my business, only to be told they were not giving me a refund anyway. Also if you are in a different timezone, that is another thing to be wary of. When I signed up they promised local support as they had two people in Australia. But these staff left and no one replaced them.
Pros:
We are a retail shop with a mechanic workshop out the back. The special order process was a positive, but unfortunately when you think of all the difficulties, costs and time loss from the rest of the system I can't go so far as to say it is a pro. The idea of the detailed security and reports options is good, but due to extensive glitches never realized any benefits. Unfortunately the reports and exports were missing data, which meant reconciliation was problematic, and the security just caused glitches and locked my staff out of the system. Due to this, the amount of bookwork to fix the mess is just huge, this system is continuing to cost me in staff costs and time even though I have left Windward. Ultimately this POS system was one of the worst business decisions I have ever made and I do not recommend it all.
Cons:
The implementation is long and tedious. We worked hard with 'technicians' to ensure quality data was loaded. We had 5 different implementation technicians as 2 left the company, one they allocated to us didn't suit the timezone, one provided intermittent help, & one was finally helpful. Windward waived some licencing fees to compensate for lack of support as we were paying for a licence we could not use. Windward then deleted all my data and we had to start again. The daily technical staff in are in a Philippines call centre, they failed to fix most issues. Due system glitches we had no choice but to leave despite due to it harming our business. A huge amount of funds and time invested. Windaward refused to provide refund despite us doing the mandatory 60 days. Glitches include BUT WERE NOT LIMITED TO: mixing up data across customer records showing machines that belonged to other customers on accounts (nothing to with our data); showing bills and outstanding amounts for other customers on accounts; continuously locking our staff out; full system outage; slowing down sales; daily sales reports inaccurate; export reports missing data. Windaward technicians use a licence you have paid for to investigate their system's issues further undermining your business as you've less workstations. We wired the internet throughout our shop as they suggested, this resolved no issues. We found usability to be poor, search functionality poor, & it would take us many steps to do basic things.
Windward can't do that, but let's try to come up with a "Workaround" for you....
Comments: Headaches
Pros:
I like the ability to special order a product on a work order and have it directly linked to the purchase order. Great for tracking an item through.
Cons:
INVENTORY!!!! There is no direct link between the inventory sub-ledger and the ledger. There is no transaction list of what is recorded in the sub-ledger, so balancing inventory and determining where an outage may have occurred is a long, tedious process that involves tracking every purchase order received, bill, work order and invoice put into the system. Implementing the software is very time consuming and self-regulated. Enhancements to the software can be requested if your company agrees to pay for the programming time to develop it.
Windward Software Response
6 years ago
Hi Nicole. Thank you for taking the time to provide your feedback with regards to Windward System Five. Glad to hear that you are finding our Special Order Tracking feature useful; it's a popular one among many of our clients. In terms of your concerns, upon review, it appears that there are, in fact, methods of solving some of the issues you are experiencing through existing product functionality. We encourage you to contact your Account Manager at +1 (800) 663-5750 to become registered for The Windward Learning Academy. This comprehensive online resource of easy-to-use product tutorials clearly demonstrates the most efficient means to use System Five by feature and scenario. In addition, we value your feedback in terms of custom enhancements. In some cases, with requested enhancements that only pertain to a very small subset of our clients, at least a portion of this development work may be billed. Widely beneficial enhancements are completed in future releases at no fee.
Scalable multi-user POS retail from a company that listens and adapts.
Pros:
Excellent customer support 24/7. A product that is scalable to your business. One of the few softwares that have a stand-a-lone ability that allow sales and lookup when the main server is offline or unavailable. Inventory orders in cases or singles by multiple suppliers with multiple part numbers and UPC codes for a single item. Capable of printing price tags on the fly when receiving. Easy lookup of products at the POS terminal by description, barcodes, serial numbers, etc. (Think about a phone caller asking for an item that is not in your hand, no numbers available and you need to quote the price.) Easy Purchase ordering. Easy resorting of POs in a fashion that matches the packing list. Complete control of forms, receipts, printers, slip printers, faxes etc. Multiple price groups and quantity price levels allowing maximum flexibility to different retail environments. Matrix pricing, kit pricing (both dynamic and static) with prices broken out or just single line on receipts. This software is our forth in 30 years and in our use since 2003. Regular updates and revisions are available to keep it fresh and up to date with changes in the ever changing retail industry. This is a very robust software and does far more than given here.
Cons:
Back office reporting is probably the weekest area. However, custom reports are available and creatable. If you are looking into any software you should have a list of what you need to know daily, weekly and monthly and have it demonstrated to you. Another area is handling price protection from manufacturers. It is not easy to drop cost on items that receive price protection. It can be done but is time consuming.
Very flexible, comprehensive software package with a somewhat cumbersome user interface.
Pros:
the flexibility thanks to various data load and import options, the ability to chain import/exports and call external scripts; detailed permission settings; the numerous features; lots of customisable reports easily ported to spreadsheet or similar.
Cons:
- documentation is very fragmented, incomplete and sometimes just wrong. - the user interface is not intuitive and a long way from modern apps. I couldnt convince our sales team to use the tasks/appointment/history-comments section as they found it too complex (but feature wise I think it's good). - the one time we needed support, we received bad advise which would have crippled this company if it had been followed. - a selection of sample scripts would really help with implementation of more complex customisations. - the unique email feature is applied across both suppliers and customers. this is problematic where a customer is also a supplier. - no support for linux pervasive engines any more. - no support for Sys5Script.exe any more. - the template editor is very unpleasant to use. Very tricky to create a visually pleasing document.
I have been using Windward System 5 as the Financial Controller for about 18 months
Pros:
Windward System 5 is well organized and intuitive for knowledgeable users. It is an extensive system doing just about anything you could want in a business management/accounting system. Reports are extensive and well laid out, and allow you to drill through to the details in most cases.
Cons:
It seems plagued with system errors. Not sure if this is just our platform, or if this happens to most users, but we get system errors on a very frequent basis (more than daily). Most are nothing and the system corrects them on its own, but some require more effort, and frequent assistance from Windward Support. Most of the support personnel are very helpful and knowledgeable, so your problems get fixed fairly quickly but they are still a nuisance.
Windward Software Response
6 years ago
Hi Ronald. Thank you for your positive review of System Five: we're pleased to hear that you find it to be well organized and user friendly. In terms of the system errors that you mention: this could indeed be related to your hardware setup. Please contact your Account Manager at your earliest convenience and discuss whether you have the minimum hardware requirements in place. In addition, if there is a recurring error that is causing you problems, please do let us know what it is and we will investigate to determine if it something we can permanently resolve.
Do not spend your money or time on this Software!
Comments: Please ask around to similar businesses and see what they are using - Do not waste your money and your time on this program. When you phone for support -you have to fight for major issues to be fixed. Every year you have to pay a lot of money for renewal and support - and you could be having a know issue that is a programming error but you still have to pay for support to have it repaired
Pros:
There isn't much I like about winward. Inventory is okay but not great.
Cons:
It is slow. Freezes. We are not a large company but it takes a long time to generate the AP/ AR reports ect. Exporting this to caseware or making you books easy access for your accountant is no existent. Which adds a major expense to a business' year end. Talk to your accountant - if they haven't heard of it - RUN! ( if they have they probably wont recommend it.) Subledger reports will not match Balance sheets: So generating an AR Report the balance will be different than the Balance Sheet. We had issues with our inventory and selling - sometimes it pulls the cost of an item twice -so it would inflate our expenses!
Best system around if you are willing to put the effort in before you go live, super easy POS side.
Comments: Best system I have ever used, to date have implemented this system in 2 businesses. This system has increased speed of transactions and lowered overheads. Best all round system.
Pros:
Have put this system in 2 businesses have had no real issues to date that have not been easy to fix. POS is pretty flawless and easy to use. You can report on just about anything. Support staff are fantastic, and implementation was easy. Windward are with you the whole way making sure everything works.
Cons:
To date have non, anything that I have ever had an issue with usually stems from user error. There are some processes that I would like to have, and they can absolutely be custom programed, like seeing what items on the invoice are have customer contract pricing, but this does not affect most sales and can be checked other ways. So not really a con just something that my end would be great, more than likely there is a way to do this. I am always learning new things to stream line the process.
windward system 5
Comments: Overall system 5 is an end to end solution which we count on to mange our business. We would like to see regular scheduled maintaince as part of our annual subscription plan. We have invested heavily in to the software on the years and would.lien to feel we can get value added serviced included.
Pros:
The software is an end to end solution for our business - we like this alot. This last year the software has slowed down which has created inefficiencies.
Cons:
The software performance has dropped as we add more users and increase the date base. The length of time it takes to book appointments has been increasing over the last two years
easy to use as you learn one area at a time
Comments: Inventory management, historical data for customers, professional POS, and financial history and tracking all in one place , and working together.
Pros:
all encompassing full service software for the business starting from the POS, inventory tracking, customer history tracking, book keeping etc.
Cons:
help guide sometimes makes it difficult to find what you need to do to get the info you want, getting the terminology or areas to look correct first.
Windward Software Response
6 years ago
Hi, Bart. Thanks very much for taking the time to provide your feedback with regards to Windward System Five. Great to hear that you're finding our suite of functionality to be useful for your business. May we please encourage you to contact your Account Manager at +1 (800) 663-5750 to inquire about becoming registered for The Windward Learning Academy. This comprehensive yet easy-to-use online resource is free for Windward clients and will assist in fully and clearly answering any product feature questions you may have.
Amazing POS system that can be intergrated with payroll
Comments: It is a great software company and always willing to help and easy to access if there is a problem.
Pros:
Easy to use and teach employees. Easy to add and track parts.
Cons:
Have not figured out how to use the special order part and see if we are ordering a lot of one part and therefore should stock that item.
Basic programming and intigration issues.
Comments: Having trouble intigrating Windward System Five, with shipping programs.
Pros:
Easy for the sales people to use, once they are very familiar with the system.
Cons:
There are basic programming errors, such as date changes, Currency type, etc. that do not flow through the je, you have to change existing je's line by line. The control numbers should change what is in the je. When I addressed the issue, I was brushed off and just told to adjust the entries. When you try to use a date range for printing vendor accounts it does not work. Trying to get it to work with other programs has been a problem, and everthing has a price tag associated with it.
SOFTWARD THAT DOES IT ALL
Comments: It took a little time to learn the features but we have been very pleased with how this software works for us in our retail Hobby Shop. We have a huge inventory which is constantly changing - no problem for Windward. Windward handles our point of sale including receivables. Tracks our purchases and payables and allows us to create reports and bar codes and so much more. I can't imagine a type of business that could not function with this very extensive software at a reasonable price. Lots of good updates and fast help available when you need it.
Pros:
Ability to design inventory reports that provide us detail on what has been sold in a date range and allows us to purchase wisely.
Cons:
Only one thing I would like to see added: A report to show income and expense in a spreadsheet by month.
Not the right system for our type of business. Probably better for a small retail company.
Pros:
I really don't know what we like most about the software. We have had the system for almost 10 years and it has never worked well for us, even after investing tens of thousands of dollars...
Cons:
Not user friendly. Expensive. Support doesn't know how to fix the problem most of the time. System not capable of performing functions that are necessary for our business. Confusing. Have spent hours and hours trying to get the system to work correctly without success. Hired someone to come help us learn the system better that cost us almost so much money and we weren't any further ahead than before they came.
Using Windward software for our small business has saved hours of time
Comments: Improved inventory management and tracking of customer service orders
Pros:
We like the way we can track service and parts for our customers and how the point of sale system tracks our inventory
Cons:
The payroll module isn't as easy to use as the point of sale module and fine tuning forms can be very confusing
Windward Software Response
6 years ago
Hi Gord -- Thank you for your feedback; we appreciate it. We're happy to hear that you are pleased with Windward System Five! In terms of operating the Payroll Module more efficiently, please contact your Account Manager at +1 (800) 663-5750 to register for The Windward Learning Academy. This online training resource will show you all the tips and tricks to operate Payroll more efficiently.