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Windward System Five Reviews

About Windward System Five

Windward System Five is a full business management system for companies that sell, service, or rent inventory.

Learn more about Windward System Five

Pros:

The cloud-based system is easy to access and use on a daily basis.

Cons:

Some of the reporting features make getting an accurate snapshot of what is occurring in the company a little difficult.

Windward System Five ratings

Average score

Ease of Use
3.7
Customer Service
3.8
Features
3.8
Value for Money
3.6

Likelihood to recommend

6.8/10

Windward System Five has an overall rating of 3.8 out 5 stars based on 188 user reviews on Capterra.

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Filter reviews (188)

Scott
Scott
Director of Operations in US
Verified LinkedIn User
Used the Software for: 6-12 months
Reviewer Source

A powerful POS with unlimited flexibility, reliable stability, and great support staff.

5.0 6 years ago

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.

Nava
Owner in US
Building Materials, 2–10 Employees
Used the Software for: 2+ years
Reviewer Source

Alternatives Considered:

Great system management

5.0 2 years ago

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.

Michelle
Office Manager in Australia
Retail, 2–10 Employees
Used the Software for: 2+ years
Reviewer Source

Would like to set up the system again knowing so much more now than was first told.

3.0 6 years ago

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.

Trina
Owner in Canada
Retail, 2–10 Employees
Used the Software for: 2+ years
Reviewer Source

System five review

4.0 4 months ago

Comments: It's a good system for what I use it for.

Pros:

fairly easy to use- good customer service -

Cons:

not clover integrated- they can't figure out how to get my statements mailed out of the system to clients properly. I have figured out a another way, it's just more work.

Rossie
Owner in Canada
Retail, 2–10 Employees
Used the Software for: 2+ years
Reviewer Source

Alternatives Considered:

Windward Software is an amazing program to help you run your business in every aspect.

5.0 2 years ago

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.

Bob
Co-Owner in US
Furniture, 2–10 Employees
Used the Software for: 1+ year
Reviewer Source

continuing forward

2.0 2 years ago

Comments: We are continuing to use System Five as migration is a challenge for a small business like ours. The support crew at Windward work well to address issues; however, our account manager failed to address items that were still in process just prior to go live. Those items remain outstanding as support is unable to address them.

Pros:

Immediate processing of credit card transactions. The fact that System 5 is in the cloud is one of the primary reasons we purchased the product.

Cons:

Not enough explanation of defaults in System 5 caused redundancy in our chart of accounts. The monthly reconciliation requires that several routines be performed before you can have a reliable balance report of income/expense reports. Modifiers were disappointing as we learned that they must be setup on an item-by-item basis, rather than a category or brand basis. Custom reporting is extremely lacking and doesn't allow for us to produce the reports we need.

Derek
Manager in Canada
Retail, 11–50 Employees
Used the Software for: 2+ years
Reviewer Source

Alternatives Considered:

Windward Review

4.0 2 years ago

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.

Tami
Systems Support in US
Recreational Facilities & Services, 11–50 Employees
Used the Software for: 1+ year
Reviewer Source

Tami McQuown

4.0 2 years ago

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

Teegan
Owner in Canada
Used the Software for: 2+ years
Reviewer Source

Gets the job done. Do not do the updates.

3.0 6 years ago

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

William
William
President in Canada
Verified LinkedIn User
Used the Software for: 2+ years
Reviewer Source

I've been a Windward user for close to 20 years. Overall, my experience is frustration.

3.0 6 years ago

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.

Ed
Partner in US
Retail, 2–10 Employees
Used the Software for: 2+ years
Reviewer Source

Using Windward in a Small Shop

5.0 3 years ago

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.

Kathi
CEO in US
Retail
Used the Software for: 2+ years
Reviewer Source
Source: SoftwareAdvice

Windward System 5 for us has grown into a great relationship.

4.5 8 years ago

Pros:

I like the auto data up loads for inventory. I like the adjustability of all the categories of forms and labels, such as invoices, purchase orders, packing slips, inventory tags, delivery tickets, etc. we can utilize and customize to suite all kinds needs for many different aspects, and situations. Being able to use the tag-a-long kits for suggestive selling, helps out the sales staff considerably, gives them that extra help in making their quotas and the don't have to remember to ask each customer, the suggested add-on items pops up on the invoice and forces them to ask. The sales staff loves the ability to bring up all their open invoices at one click. They love the ability to prioritize estimates for their follow ups. I love the pop up tasks, I can assign tasks to specific employees for a specific day and time to pop up, to remind them to get it done. Using system batch purchasing really saves a lot of time. Using alternative vendors for the same products helps with our inventory management. We have a repair department, sometimes the sales people will help out on the repair bench and the "technician's time clock" works well for them when they get call back to the sales floor in the middle of their repair and then come back later to finish, that may happen several times in the course of one repair depending if the time it takes for completion. Using this "technician's time clock" makes it easy to track their time for the repair fees. System 5 is such an integral part of our day to day functions, we take a lot of it's features for granted, it is hard to think of all the good things it does for us to make our lives easier.

Cons:

I think the data up loads can function easier, be less complicated. We don't use the accounting part of the program. We use QB for our payroll and it will integrate with System 5 so that is good. There are more aspects of the program I like to be using and I wish the learn curves would be easier. We have an extra large amount of inventory and data stored in the system, since we have been using it since 2008. When generating reports or gathering information, the delays to the system or the machine's think processes, are way too long for me, before the abort button shows up, if it shows up at all or the option to quit the process and try another way. Again think of what I like least is difficult to do because we always find a work around to fulfill our needs.

Pete
Canada
Used the Software for: 6-12 months
Reviewer Source

This is NOT a Rental Software

1.0 7 years ago

Comments: We were running a good rental software program when we were approached by a Windward Software salesman who convinced us that we should give Windward a try. The salesman made us all kinds of promises, which we found out later were not all true. For example: don't believe it if
they tell you that they migrate your data, we ended up doing this all ourselves. On the surface, the Windward Program seemed to be a good rental system. It had a good inventory based set-up, We ended up repeatedly having this incomplete transaction screen popup. When we called for tech support to fix this problem, they would tell us to fix it ourselves, either by editing a single transaction or by p.o.s. This proved to be very difficult, and very time consuming. A program should never do this every day, and if it does the company should take responsibility to fix it, not the customer. This was the most unstable program from any we have used. We spent many days without our program working, due to their unreliable techs. This program was a nightmare for our accounting department. The accounting department had their workload tripled, due to the fact that the daily closing reports were not correct. We ended up creating a worksheet of every transaction for the closing period and transferring the data to make our journal entries for the day. In most cases their accounting techs didn't know what they were talking about, they never really fixed our problems, but instead told us, just reverse the transaction and do it again, the paper work piled up so much that we had to give an employee some time off for stress leave. This software would be a good inventory or p.o.s system , but it's definitely not designed for a rental or accounting system. All they did is add a rental module to an existing point of sale system, if you rented only 1 or 2 machines a day it would probably work, but if your main business is rentals, you would not want this system

Pros:

This software would be a good inventory or p.o.s system

Cons:

it's definitely not designed for a rental or accounting system

Ian
Director in
Retail, 11–50 Employees
Used the Software for: 6-12 months
Reviewer Source
Source: SoftwareAdvice

I have a 8 user licence. Many bugs and some functionality falls short. As if they did not think the whole process through properly. Financial side is very cumbersome. I am looking for alternate solutions.

2.0 7 years ago

Comments: Read all the reviews. This software could really be good if it was finished strong and some further thought was applied to the processes. It seems 80% complete with shortfalls in many areas. Financials are just not suitable for our size of business. It takes 4x the amount of time to complete a task compared to QB. My accountants find this aspect frustrating. They really should offer an integration with QB for those who want it. It feels like they are trying to cover too much in this software. I have some tickets on issues and bugs for over 3 months now and they still have not been completed. Of what I know now, I would not have purchased this software. I am looking for alternate software.

Pros:

The sales aspect is good. POS is acceptable. Easy to find a product and sell it. Kits work well. Reporting is somewhat good. Support tries to resolve issues.

Cons:

Financials - If you are serious about your business, this is not for you. It is not comparable to Quick books. They have flatly refused to integrate with QB. Their financial side scores a 1/10. The Multi currency module is full of promise but has many problems and bugs like display and operational issues. You have to be very careful when dealing with multi-currency. Procurement is quite basic and could have been thought through more. No real science or maths behind ordering so you better know your high, lows, trends etc. Some aspects are good but fall short in some areas. They state they are PCI compliant but fall short on monthly account payments. There is a work around but wastes time. If you do job cards or outwork, this is a challenge and you have to invent your own internal systems. Not sure on stock value integrity? Stock take process could have some enhancements to make it quicker for the user.

Adirna
Accounting Manager in Canada
Machinery, 11–50 Employees
Used the Software for: 2+ years
Reviewer Source

Inventory Management

2.0 2 years ago

Comments: This software is actually causing us more work than it is relieving. We are having to manually check a lot of our inventory as we cannot trust the system to track it effectively.

Pros:

The upfront interface is easy to follow.

Cons:

Once we moved to the cloud the program became very unstable. Everyone is running a different version. It seems that you only get to upgrade to a new version if you complain about functionality not working. It is slower than a server version as you are logging onto their remote server. Running reports has become cumbersome as you have to run on their remote desktop and copy to your own. We have had issues with inventory which is a critical part of our business. It can take them up to 2 weeks to get critical fixes completed or for you do discuss with a developer because tech support can't help you.

Windward Software Response

2 years ago

Thanks for the feedback Adirna. All Cloud customers are eligible for our new releases as they occur. You can request an update by contacting support. Please reach out to your Account Manager for your speed concerns. We have some new reporting modules that may help with your speed concerns. We can also review your cloud setup.

Julie
Controller in Canada
Wholesale, 11–50 Employees
Used the Software for: 2+ years
Reviewer Source

Windward System Five

5.0 3 years ago

Comments: With Windward we are able to use the reports to budget for the future, look at our sales history per customer, get customer reports that we need.

Pros:

I like the ease of being able to run our day to day business. We use the software all day every day. The ease of checking our inventory is terrific. Setting up a new customer is very easy. The system is very easy to use. Moving the data from our old system to Windward was very easy. We were able to import with very little mistakes.

Cons:

I really don't have any cons with the software except that it is sometimes hard to set up new reports that we would like to download. Some times the help feature is not very specific for the reports that I need

Grant
IT Manager in Canada
Retail, 2–10 Employees
Used the Software for: 2+ years
Reviewer Source

Alternatives Considered:

Good POS Order Management Software

5.0 2 years ago

Comments: Very happy with the software. They worked with me in implementing and transferring our data with only a few hickups.

Pros:

Order Management, POS, Inventory Tracking.

Cons:

Not as customizable as I would like. Email feature lacks templates for the email body of the message when sending statements in bulk. Could have a better more customizable email feature for invoices and statements.

RALPH
STORE MANAGER in US
Retail, 11–50 Employees
Used the Software for: 2+ years
Reviewer Source

Customizable to a variety of business types. Fairly easy to use and learn the basics.

4.0 6 years ago

Comments: One software that we can use for the front end of the business and the back.

Pros:

I like being able to customize buttons at the cash registers and change them seasonally as we are a garden center and our products do change drastically with the seasons. Customer support is always very helpful and has fixed most issues that I have had in the past. We make our nursery signs, labels, and a variety of different types of price tags within System Five. No need for another program as we did need one in the past. I have not used them yet but having webinars and a learning area available to us is an excellent way to get more out of our software.

Cons:

Customer tech support is very good, however I think that it is a bit expensive annually. The label and form designers work but do not seem to be what you see is what you get. It takes a little finessing to create a label that fits your media properly.

jody
general manager in Canada
Hospital & Health Care, 11–50 Employees
Used the Software for: 2+ years
Reviewer Source

windward system 5

4.0 2 years ago

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

Bart
owner in Canada
Used the Software for: 2+ years
Reviewer Source

easy to use as you learn one area at a time

4.0 6 years ago

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.

Stephine
Office Manager/ Owner in Canada
Automotive, 2–10 Employees
Used the Software for: 2+ years
Reviewer Source

Amazing POS system that can be intergrated with payroll

5.0 2 years ago

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.

Christine
Controller in Canada
Automotive, 11–50 Employees
Used the Software for: 2+ years
Reviewer Source

Basic programming and intigration issues.

3.0 2 years ago

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.

Angie
Administration in Canada
Consumer Goods, 2–10 Employees
Used the Software for: 6-12 months
Reviewer Source

It has been a steep learning curve. Things are getting better all the time

4.0 6 years ago

Comments: Much better control over our inventory and keeping track of all our product. The PO and receiving makes it easy to know when someones product comes in. We are tweaking the software constantly as we learn new things. The webinars and academy have been a big help.

Pros:

Very versatile, learning new things all the time. Everything meshes together in one package. Like the way you can drill down to see what happens in the background. The accounting took a bit of getting used to but has proved itself .

Cons:

The Terminology is different from most other programs and it is sometimes difficult to determine exactly what a certain term means

Windward Software Response

6 years ago

Angie, thank you for taking the time to provide your feedback relating to Windward System Five. We're happy to read that our software is meeting your business needs. In addition, it's great that you are attending our weekly webinars and using The Windward Learning Academy; both are designed to assist you and/or your staff with further learning of System Five functionality. If you have any questions or concerns at any time, please do not hesitate to contact your Account Manager at +1 (800) 663-5750.

Heather
owner in Australia
Retail, 2–10 Employees
Used the Software for: 2+ years
Reviewer Source

why I use windward

4.0 2 years ago

Comments: When we first started with windward it was fantastic. If we needed support, we called in Australia and it was fixed. Now there is no point in using that phone number! It then seemed the support workers did not know windward very well and I was brushed off or it would take a long time to resolve the issue. I must say it is getting better but not as good as it once was.

Pros:

This system fits our needs with long part numbers. We are not computer people so the support is very important to us.

Cons:

Some times it takes so long to get the support we need. The was such an issue I did think about changing systems. It has got better.

Lynea
Owner in Canada
Wholesale, 2–10 Employees
Used the Software for: 2+ years
Reviewer Source

Windward System Five - I would recommend this program

5.0 2 years ago

Comments: Windward System Five is an easy to use program that allows people who have little experience to use it.

Pros:

Inventory Control is very functional and easy to use.

Cons:

Reports are difficult and you have to build most of your own reports so you need to be skilled with it. Also if a tax changes on a product you have to make a new product code and start over for that item.