# Windward System Five Reviews 2026. Verified Reviews, Pros & Cons | Capterra > Is Windward System Five the right Retail Management Systems solution for you? Explore 189 verified user reviews from people in industries like yours to make a confident choice. Source: https://www.capterra.com/p/43189/Windward-System-Five/reviews --- Windward System Five 3.8 (189) [View alternatives](https://www.capterra.com/p/43189/Windward-System-Five/alternatives/) Provider data verified by our Software Research team, and reviews moderated by our Reviews Verification team. [Learn more](https://www.capterra.com/our-story/) * * * Last updated March 13th, 2026 # Reviews of Windward System Five Ease of use 3.7 Customer Service 3.7 ## Pros and Cons in Reviews MB Mason B Sales AssociateConsumer Goods, 2 - 10 employeesUsed the software for: 1-2 years. “Searching for historic records of customer purchases, inventory tracking over time, and loyalty program points still works very well.“ August 1, 2025 MB Mason B Sales AssociateConsumer Goods, 2 - 10 employeesUsed the software for: 1-2 years. “An outdated and clunky UI makes it much harder to utilize to its full capabilities, occasional long loading times, and annoying notifications about users connected to different pieces of hardware.“ August 1, 2025 JG Jeff G PARTS MANAGERAutomotive, 11 - 50 employeesUsed the software for: More than 2 years. “The system has many good functions and tracking abilities.“ April 30, 2024 JG Jeff G PARTS MANAGERAutomotive, 11 - 50 employeesUsed the software for: More than 2 years. “That function does not exist and system 5 support team as well as account manager act as if I am the first person/business to want this incorporated into the system.“ April 30, 2024 NC Nava C Owner Building Materials, 2 - 10 employeesUsed the software for: More than 2 years. “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. “ July 6, 2022 GH Greg H OwnerRetail, 2 - 10 employeesUsed the software for: More than 2 years. “It would appear that no one at Windward has EVER used the software for any length of time because bugs and usability issues persist for all eternity.“ June 18, 2025 KM Kathi M CEORetail, 2 - 10 employeesUsed the software for: More than 2 years. “We couldn't do without them and their service is fantastic. “ June 6, 2024 SH Shauna H Accounts Payable Manager and Bookkeeping AssistantRetail, 11 - 50 employeesUsed the software for: More than 2 years. “The bugs that can happen where the system is not updating correctly.“ November 13, 2024 ## Showing most helpful reviews Showing 1-25 of 189 Reviews Sort by: Most Helpful Rating Company Size Reviewer's Role Length of Use Frequency of Use Mark H. IT Manager Used the software for: 2+ years ### "Highly customizable software that you can really tailor to your business for an affordable price." October 27, 2017 5.0 Reduced IT costs, Improved staff experience and greater overall efficiency of our business practices. Pros I give this review after having tried many different software packages over the last 15 years. Some costing x10 the price of Windard, some costing x10 less. What I'm left with over these years is perspective, and that perspective was hard earned. You will not find a more complete point of sale, inventory control, accounting, crm, etc. for this price range. With the ability to fine tune it to your exact business needs, it's easiest to configure, maintain and operate...especially compared to the "enterprise" software world where your eyes will water from pricing. Its got lightning fastest Point of sale with the absolute best part find search tool I can recall using. The special order management is the best complete solution from any I've tried. If your serious about your Business, you should consider Windard. I honestly think that in the long run it has improved our business, staff and bottom dollar. Cons There is no such thing as perfect software. With that being said, there are issues...but then it's technology. You have to considering that it is a highly customizable product that able to serve an amazing range of business types with thousands of options. What Windward has that sets it apart is a fantastic support team with Canadian staff and an out-of-country team that is admittingly fantastic...probably the best off-shore support that I have ever experienced in IT. Tech support is typically same day, commonly instant or within a few hours of placing a call. If you have an urgent problem, they will find someone for you RIGHT NOW. If you have problems using Windward software...you will most probably have problems using another piece of software. The key with any software, especially if you are new to it, is to have patience and use every opportunity to learn. Review Source Response from Windward Software November 6, 2017 Mark, thank you very much for taking the time to provide your feedback on your experience with Windward System Five. We're thrilled that you are very satisfied with our software! As you identify in your review, Windward Software is committed to continuously improving our business management solutions such that we may continue to offer the most user-friendly, yet comprehensive functionality available. TM Tami M. Systems Support Recreational Facilities and Services Used the software for: 1-2 years ### "Tami McQuown" June 27, 2022 4.0 Its been a great experience! Pros Ease of use, technical support answers all questions Cons Credit card transactions did not go well at first Reason for choosing Windward System Five A true POS system Switched from [QuickBooks Enterprise](https://www.capterra.com/p/174984/QuickBooks-Enterprise/) Needed more features, all in one, a true POS system Review Source ZW Zoe W. Owner Retail Used the software for: Less than 6 months ### "I wish I never heard of Windward Software" November 16, 2020 1.0 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. Review Source Marie V. Owner/Operator Used the software for: 2+ years ### "This softwear has made our business extremely essential to operate." October 26, 2017 4.0 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. Review Source Response from Windward Software November 6, 2017 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. Ketan H. General Manager Used the software for: 2+ years ### "it has been great and have found it very user friendly and easy to use" November 13, 2017 4.0 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 Review Source Response from Windward Software November 14, 2017 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. Kathy H. Business Owner Used the software for: 2+ years ### "The ecommerce support is not 7 days a week unfortunately. Otherwise a great software and support. " October 26, 2017 5.0 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. Review Source William P. President Used the software for: 2+ years ### "I've been a Windward user for close to 20 years. Overall, my experience is frustration." November 8, 2017 3.0 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. Review Source Mark M. President Used the software for: 2+ years ### "WWS5 is a workhorse! " November 11, 2017 5.0 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. Review Source Ed M. Owner Used the software for: 2+ years ### "Wondward Software is taking us to the next level of POS sales, service & support." October 26, 2017 4.0 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. Review Source Response from Windward Software November 7, 2017 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. Ken F. Owner Used the software for: 2+ years ### "overall pretty good. As good as others in the market" October 27, 2017 4.0 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, Review Source Response from Windward Software November 6, 2017 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. TY TODD Y. manager/it Retail Used the software for: 2+ years ### "Windward and You. The tutorial." February 10, 2021 5.0 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. A report that can show me all items sold per book month with the following parameters. sales clerk name, Invoice #, Date of sale, Customer name, Qty, Item #, Price ea., & Price total. A report that will pull ALL items. (stock, Non-stock). Currently i have to use 2 different reports, export to excel, and then combine them to create the report i need to send to suppliers for their sales incentives (spiffs). Granted this is alot better than the old computer system, but still takes longer than it should. side note: i have seen and experienced so far that if someone requests an addition, that the programs will do ONLY what was asked for. Example: you were asked to increase item #'s and part #'s to 50 characters. That was done, but they didnt change non-stock special orders where you have to manually type in the characters. When i caught this problem and brought it up to tech and the programers, the response was " they didnt ask for that to be done" and "it is what it is". Same with items i listed. can data load, but not put on reports. Reason for choosing Windward System Five it fit the bill for what we wanted and we thought it was what we needed. Review Source Response from Windward Software April 3, 2021 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! jG jody G. general manager Hospital & Health Care Used the software for: 2+ years ### "windward system 5" June 20, 2022 4.0 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 Reason for choosing Windward System Five The overall end to end solution was better with system 5 Review Source MH Michelle H. Office Manager Retail Used the software for: 2+ years ### "Would like to set up the system again knowing so much more now than was first told." October 31, 2017 3.0 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. Review Source Response from Windward Software November 3, 2017 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. AF Adirna F. Accounting Manager Machinery Used the software for: 2+ years ### "Inventory Management" July 5, 2022 2.0 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. Review Source Response from Windward Software August 8, 2022 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. TM Trina M. Owner Retail Used the software for: 2+ years ### "System five review" December 18, 2023 4.0 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. Review Source AU Anatoly U. owner Retail Used the software for: 2+ years ### "Stay Away, poor Company and Poor program full of glitches" September 2, 2023 2.0 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 Review Source Response from Windward Software September 6, 2023 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 sales@windwardsoftware.com so that we can discuss. MN Michelle N. Bookkeeper/ Admin Retail Used the software for: 2+ years ### "frustrating! Too many issues way too often" November 2, 2017 3.0 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 Review Source Response from Windward Software November 6, 2017 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. VV Victoria V. Accounts Receiable Building Materials Used the software for: 2+ years ### "Feeling Confident" January 26, 2021 4.0 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 Reason for choosing Windward System Five Although I was not working for the company when these chose this product - having worked at other companies, this program was fairly easy to negotiate. Review Source Response from Windward Software February 17, 2021 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 that topic: https://blog.windwardsoftware.com/windward-insider/design-inventory-reports-get-insights-make-informed-decisions If you would like some one-to-one training and help with reporting, you may want to check out the Reporting package from the Windward Professional Services Catalog. The bottom line is that we're here to help you improve and get more from Windward System Five. If you have any questions or concerns, please do not hesitate to contact us at any time: +1 (800) 663-5750. IK Ian K. Director Retail Used the software for: 6-12 months ### "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." September 26, 2017 2.0 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. Review Source GF Grant F. IT Manager Retail Used the software for: 2+ years ### "Good POS Order Management Software" June 30, 2022 5.0 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. Alternatives considered [Fishbowl](https://www.capterra.com/p/123794/Fishbowl/) Reason for choosing Windward System Five Better developed product and support. Review Source SB Sylvie B. Book Keeper Machinery Used the software for: 2+ years ### "Do not spend your money or time on this Software! " March 18, 2019 2.0 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! Review Source DR Dwayne R. President Events Services Used the software for: 2+ years ### "Software is still limited on the rental side. " November 21, 2017 4.0 We started with this software, it is still fairly limited on the rental side but it is costly to change. Pros Easy to use for the basic functions of our business such as reserving, renting and returning product. Integrated POS. Cons Limited as far as scheduling for logistical planning, very basic and a lot of potential for mistakes, too manual in some respects. Rental reports need to be simplified the variety of reports needs to be expanded. Generally there needs to be more reports that are specific to the rental side designed by Windward that help to identify business opportunities as well as areas the business could improve in. Review Source Response from Windward Software November 27, 2017 Hi Dwayne, thank you for taking the time to provide us with your feedback. In terms of your experience with the System Five Rentals Module, may we please suggest speaking to your Account Manager at +1 (800) 663-5750 to become registered for The Windward Learning Academy. This comprehensive online resource will provide you with user-friendly tutorials to craft advanced reports as well as to gain access to more detailed Rentals functionality. In addition, please stay tuned for Windward Intelligence, an upcoming System Five enhancement that provides integration with Microsoft Power BI, which will enable our users to run custom reports. PH Paul H. Owner Retail Used the software for: 1-2 years ### "My review" June 27, 2022 3.0 Able to handle our large inventory Pros Inventory volume control, inventory adjustments Cons Clitches, slow, trade ins difficult, doesn’t round on account payments Switched from [Sage 50 Accounting](https://www.capterra.com/p/174753/Sage-50cloud/) Wouldn’t handle our inventory volume Review Source PB Pat B. Website/Software/Data Facilitator Computer Software Used the software for: 2+ years ### "In 2009, Windward helped us organize and track merchandise for the first time - big benefit!" October 26, 2017 4.0 Do you mean Windward or Capterra? I already described our Windward benefits in the review. Capterra I hope will help me win the Surface Pro Windward is offering in its contest! ;-) Pros Have been a user/admin since 2009, and have been through many upgrades and improvements. It's easy to set up routines to track all incoming and outgoing merchandise and expenses. It seems to integrate well with accounting. You can extensively customize reports and you can easily export files from any report. Software is durable and forgiving; almost never freezes despite robust use from our end. Cons Emailing invoices has been problematical over the years. Windward hasn't integrated well with third-party email management software like Outlook and Thunderbird, although this situation may have improved since last I checked (this function is only sporadically my responsibility in the business). Some of our seats/terminals work, some do not. Customer service was baffled. Also, customizing forms can be a little tricky, but we have managed that. Review Source ET Eva T. Controller Automotive Used the software for: 2+ years ### "Ease of Use with Nice Features" July 5, 2022 4.0 Over the years there was a lot of frustration with support but it has been getting better and quicker Pros The system is very user friendly for the basic user and with a little experience on it you can become a whiz quickly Inventory tracking when used correctly is awesome!! Nice to have a Floorplan system that tracks from purchase to payout Cons I would like it accessible on mobile as we are on the cloud and that was kinda what was expected but did not get it Review Source Similar Products Featured ## Send me user reviews about this product ### Fill out the form and we'll send a list of the top-rated software based on real user reviews directly to your inbox.