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Windward System Five

Cloud-based business management solution | ERP for your SMB

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Windward System Five Reviews

Overall rating

3.8

/5

187

Rating criteria

  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend7.62/10

Reviews by rating

Pros and cons

I like how it is inventory control and accounting integrated into one system. The system has great abilities.
It truly has the ability to accommodate anything I want to do to operation my business more efficiently. System Five is a very user friendly product that is easy to learn and understand.
Great customer service and great software. Can do pretty much everything you need for you 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.
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.
When we have to call for tech support we have to talk to someone over seas and most of the time our connections are terrible. Hard to hear or understand and calls are dropped.
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187 reviews

Recommended

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Kathy H.

Used daily for 2+ years

Review source

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend9/10

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The ecommerce support is not 7 days a week unfortunately. Otherwise a great software and support.

Reviewed 5 years ago

I thoroughly reviewed 4 different POS software systems prior to making a purchase. It was important to choose the software that would grow as my business grew. Out of the POS systems available at that time (6 years ago) this was the best to fit the needs of my business then and into the future. Now, 6 years into it, this has proven to still be the best choice. It has allowed us to continue with the same software system as the business has grown and evolved.

Pros

It fill all of our needs as a retail store as well as a webstore. It integrates both of those nicely. The accounting and the POS in one system is a great way to run a business.

Cons

In my business it would be useful to give employees access to a variety of information screens. Windward does allow this to some extent, but not to the extent that makes it practical in our situation. Which sometimes forces me to give people access to confidential information which they don't need in the coarse of their job.

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Marie V.

Used daily for 2+ years

Review source

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend8/10

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This softwear has made our business extremely essential to operate.

Reviewed 5 years ago

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.

Vendor response

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.

MN
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Michelle N.

Retail, 11-50 employees

Used daily for 2+ years

Review source

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend4/10

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frustrating! Too many issues way too often

Reviewed 5 years ago

I will have to think about that

Pros

Knowing that you can pretty much always get a hold of someone in support- My all time favorite support person really knows what she is doing and is a very pleasant wonderful personality! It is nice that there are a variety of reports for each department

Cons

The bookkeeping part of Windward - everything is journal entry based and not check book based - The payroll system is Canadian based and is not United States friendly on the forms that need to be done at year end for payroll and the government. Some of the reports don't print dates and other pertinent information on them and if they do you have to click on everthing to just read the notes. Also an awful lot of "errors" that occur and some that never get fixed- it tends to be frustrating! Also having to wait for someone to call you back when there is a urgent issue that needs addressing asap can get frustrating, although you do always get a call back

Vendor response

Hi, Michelle -- thank you for taking the time to provide your feedback relating to your experience with Windward System Five. We're pleased to hear that you are satisfied with our Customer Support team; we ensure that all of our clients are answered by a real person at any time, day or night. In terms of your concerns, we are confident there are in fact methods to overcome your stated issues. We encourage you to please contact your Account Manager at +1 (800) 663-5750 in order to gain access to The Windward Learning Academy. This comprehensive online training resource is easy-to-use and will answer questions related to any type of System Five functionality, including Payroll.

GF
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Grant F.

Retail, 1-10 employees

Used daily for 2+ years

Review source

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend9/10

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Good POS Order Management Software

Reviewed 7 months ago

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.

SB
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Stephine B.

Automotive, 1-10 employees

Used daily for 2+ years

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Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend9/10

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Amazing POS system that can be intergrated with payroll

Reviewed 7 months ago

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.

RD
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Ronald D.

Used daily for 1-2 years

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Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support

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I have been using Windward System 5 as the Financial Controller for about 18 months

Reviewed 5 years ago
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.

Vendor response

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.

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William P.

Used daily for 2+ years

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Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support

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

Reviewed 5 years ago

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.

HA
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Heather A.

Retail, 1-10 employees

Used daily for 2+ years

Review source

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend5/10

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why I use windward

Reviewed 8 months ago

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.

BA
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Bob A.

Furniture, 1-10 employees

Used daily for 2+ years

Review source

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend10/10

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A life saver

Reviewed 8 months ago

As business exploded we were able to keep up to the increases in stock levels,expected stock and tagging stock already on order for specific clients.

Pros

There are many ways to find what ever it is you need to know. Much of the system is logical. From finding customer to products ,it has a report for everything.

Cons

Data entry is easy unless your dislexic. Upgrades are hard to keep updated again ,the users fault.

IK
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Ian K.

Retail, 11-50 employees

Used daily for 6-12 months

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Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend1/10

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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.

Reviewed 5 years ago

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...

TY
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TODD Y.

Retail, 11-50 employees

Used daily for 2+ years

Review source

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend8/10

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Windward and You. The tutorial.

Reviewed 2 years ago

We have solved issues with double ordering Special Orders, have streamlined Purchase Orders, Receiving, Price Changes, Showroom tag printing. I am able to compile reports simply, where it use to take days. Taking inventory is so much faster using data collectors and being able to import the files.

Pros

Our old system was very outdated and Windward has made it so much simpler and quicker to get our monthly/quarterly reports. Integration between order taking and purchasing has helped speed up the ordering process & stop mistakes being made. Love the virtual warehouse option.

Cons

What i feel is missing is: 1. Freeform 1 & 2 can be data loaded in. Freeform 1 can be on a report, but Freeform 2 can not. 2. Sales/Upsell warnings can be on a report, but not data loaded. 3. Purchase warnings can be data loaded, but not put on a report. (Invoice Warnings can be data loaded & put on a report) 4. There is no where to search "Non-Stock Special Orders" by number or supplier in history. 5....

Vendor response

Hi Todd, Thanks for taking the time to write this! Other lighting showrooms that may be considering Windward will find this helpful. As for your reporting concerns, we may be able to help through a project plan from the professional services catalog which would be a great place to start to explore existing functionality. https://www.windwardsoftware.com/resources/professional-services.html There is also the option to do some custom programming if you have requirements that cannot be handled by the current reporting tools. We are looking forward to many more years of service to Grand Rapids Lighting. Thanks again Todd!

KM
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Kathi M.

Retail,

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Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend10/10

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

Reviewed 7 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,...

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.

Vv
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Victoria v.

Building Materials, 11-50 employees

Used daily for 2+ years

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Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend7/10

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Feeling Confident

Reviewed 2 years ago

Have learned a tremendous alot this year, in particular about inventory - still a long way to go.

Pros

Overall it has been pretty easy to learn this program

Cons

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

Vendor response

Hi Victoria, Thank you for taking the time to write a review! More importantly, thank you for investing time in learning more about how Windward works for your business. We appreciate your comment about reporting. Since there are so many reports available it is sometimes hard to nail down one that works best for you. There's also the option to design your own reports. Here's some info on...

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Ketan H.

Used daily for 2+ years

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Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend9/10

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it has been great and have found it very user friendly and easy to use

Reviewed 5 years ago

more up to date information and tracking of items with serial numbers, it was easy to set in place policies and see where we lacked and brought in a lot of controls in the company

Pros

the software is easy to use and customizable. we have found a it works well and have not had too many problems. there are a lot of options in the setup and we are able to change if it does not work. the implementation staff was great and the support is great. when ever I have contacted support they responded very quickly and the webinars have helped make the software better

Cons

it takes a long time to get a feature added and a lot of pestering, there are a few things in the software that does not make sense with the labels

Vendor response

Hi Ketan -- thank you for taking the time to provide us with your feedback. Great to hear that you're pleased with Windward System Five, our Implementation Team, and weekly webinars. In terms of custom feature development, we record all requests and work diligently to include this functionality (when possible) in subsequent product releases. To learn more about upcoming System Five features, please contact your Account Manager at +1 (800) 663-5750.

JM
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Julie M.

Wholesale, 11-50 employees

Used daily for 2+ years

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Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend9/10

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Windward System Five

Reviewed 2 years ago

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

RM
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RALPH M.

Retail, 11-50 employees

Used daily for 2+ years

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Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend8/10

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

Reviewed 5 years ago

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.

BK
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Bilal K.

Furniture, 1-10 employees

Used daily for 2+ years

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Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend9/10

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Windward Software System

Reviewed 2 years ago
Pros

Nationwide Furniture Mattress Outlet looks forward to continuing and growing our partnership with Windward Software. Windward Software's system allows us to stay on track and be able to organize vital information. We rely on Windward Software to perform every day so we can deliver the best customer experience possible

Cons

The time it takes to load certain functions is excessive sometimes.

Vendor response

Hi Bill, Thank you for taking the time to write a review! It truly helps other business owners like yourself make a decision that will help their operation grow much like yours has. As for your speed comment, there have been some improvements within some of the reporting tools. If you haven't already done so, try upgrading to the newest version and if that doesn't resolve your issue, please place a ticket in your support portal at support.windwardsoftware.com. Thanks again Bill!

AT
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April T.

Retail, 1-10 employees

Used daily for 2+ years

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Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend10/10

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The benefits more than outway the problems that occur

Reviewed 5 years ago

All in one program for inventory to A/R and A/P etc.

Pros

Inventory control and details that can be entered into each item is awesome. Customer sales tracking is great. Can be adapted to many types of businesses.

Cons

Reports side is not the best. Cannot get an accurate back dated inventory and designing reports is sometimes hard. Need bigger field for invoice numbers when adding bills to workorders.

Vendor response

Hi April, and thank you for taking the time to provide us with your feedback. We're delighted to hear that you are happy with System Five's tracking capabilities. In terms of some of the issues you are experiencing with reporting, may we suggest that you contact your Account Manager at +1 (800) 663-5750 and request registration for The Windward Learning Academy. This easy-to-use yet comprehensive online tutorial resource will guide you as to how to best utilize reporting and generate the exact reports you're seeking.

AR
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Verified reviewer

Retail, 11-50 employees

Used daily for 2+ years

Review source

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend7/10

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Lots of great features but maybe too many for a small business

Reviewed 5 years ago

We can now track customer purchases more easily. Inventory control is faster and easier than before.

Pros

This program has a lot of features, many of which speed up the tasks we perform daily. Tracking our customers is now fairly easy. Most of the system is Excel compatible which makes invoices and other documents easy to export. Windward's tech support is very friendly and accommodating.

Cons

As useful as this software is I still find simple tasks that it cannot perform. I have made at least four requests of tech support concerning software functionality that resulted in an answer of "the software can't do that" (and my requests were far from complicated). It's as if the software is so good at doing a million different tasks that it wasn't built to do the simplest ones.

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Mark M.

Used daily for 2+ years

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Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend10/10

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WWS5 is a workhorse!

Reviewed 5 years ago

Ease of Use Inventory control Order management Work flow Simplification and tracking Emailing Invoicing Accounting

Pros

Windward System 5 has been a workhorse for our business for over 12 years! We can control our inventory, track special orders, email clients and much more with WWS5. We have been able to grow into this software. There are many features that we are still learning that are simplifying our workload! I highly recommend System 5 to anyone who manages inventory. BTW the reporting capabilities are almost endless.

Cons

It is a little quirky, but the benefits far outweigh the quirks. I wish that it had more web integration or that they would offer cloud based databases.

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Ed M.

Used daily for 2+ years

Review source

Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend8/10

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Wondward Software is taking us to the next level of POS sales, service & support.

Reviewed 5 years ago

An All in One Sales, Customer tracking, Promo & follow up, Bookkeeping & Accounting Software With Great Support.

Pros

Back office accounting is saving us money by tracking inventory vs sales, as well as less cost with accounting fees by running an all inclusive bookkeeping/accounting program.

Cons

The occasional glitches, after each windows update, with form display screens freezing up the software.

Vendor response

Thank you, Ed, for taking the time to provide us with your feedback and for your positive comments: much appreciated! We are committed to ensuring that Windward System Five is 100% seamless in operation with all future Windows releases. That said, if you experience any issues please contact our Customer Support Team at any time for assistance: +1 (800) 663-5750.

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Ken F.

Used daily for 2+ years

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Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend7/10

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overall pretty good. As good as others in the market

Reviewed 5 years ago
Pros

POS screen is very easy for staff to learn. Transactions easy to process. Lots of reports available

Cons

Update to windows 10 a costly extra. Payroll function lacking. Designing forms takes a lot of work,

Vendor response

Hi Ken -- thank you for providing your feedback relating to your experience with Windward System Five. We're happy to hear that you are pleased with System Five's level of functionality. In terms of the Payroll module, we encourage you to contact your Account Manager at +1 (800) 663-5750 to become registered for The Windward Learning Academy. This easy-to-use, yet comprehensive online training resource will provide everything you need to know about efficiently using our Payroll module, designing forms, and other system functions.

LB
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Lynea B.

Wholesale, 1-10 employees

Used daily for 2+ years

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Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend8/10

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Windward System Five - I would recommend this program

Reviewed 7 months ago

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.

MC
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Mike C.

Used daily for 1-2 years

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Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support

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consistent problems with functionality

Reviewed 5 years ago
Pros

serial number tracking and customer purchases tracking. Ability to do rental and the capability to track rental

Cons

consistent issues with day to day operations and functionality. Unable to work thru most issues without a call to the tech department which has to call you back

Vendor response

Hi Mike, thank you for taking the time to provide us with your feedback. We would like to assist you resolve any questions you have regarding functionality. Please contact your Account Manager at your convenience and we will discuss your needs in more detail. In addition, please ask your Account Manager to provide you with access to The Windward Learning Academy. This is a comprehensive online set of searchable tutorials that will provide you with clear direction in terms of using System Five for all types of functionality and is a resource that you can use at any time.

LN
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Lori N.

Sporting Goods, 1-10 employees

Used daily for 2+ years

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Overall Rating
  • Value for money
  • Ease of use
  • Features
  • Customer support
  • Likelihood to recommend5/10

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Have been using Winward for 5 years and it is very frustrating.

Reviewed 5 years ago
Pros

Journals are easy to do same with cheques and we have a lot of control in that area. The support people always try to help and are very pleasant, but very often even they can't figure out how to fix something.

Cons

Very hard to delete stock or move it around, certain GL accounts we can't access, puts in transactions in the back ground that we don't about and screws up the Balance Sheet and difficult to delete a PO. In general it's difficult to delete anything except for cheques and journals which should be a little more protected.