# Windward System Five Reviews 2026. Verified Reviews, Pros & Cons | Capterra > Is Windward System Five the right Accounting 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) 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 June 14th, 2026 # Reviews of Windward System Five Ease of use 3.7 Customer Service 3.7 ## Pros and Cons in Reviews Comprehensive inventory tracking tools 82% positive reviews out of 45 Most reviewers describe inventory management as detailed, efficient, and helpful for tracking stock, pricing, and reporting. Mason B Sales Associate, 2 - 10 employees. "Searching for historic records of customer purchases, inventory tracking over time, and loyalty program points still works very well." Slow and inconsistent support service 46% negative reviews out of 78 Most reviewers indicate customer support is slow, difficult to reach, and often fails to resolve technical problems. Frequent software glitches and errors 89% negative reviews out of 36 Most users report bugs and issues disrupt daily operations, with recurring errors, slow fixes, and persistent glitches. Greg H Owner, 2 - 10 employees. "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." ## 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. 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. 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 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. Bruce G. Co Owner Used the software for: 2+ years ### "Overall a very versatile product! " October 26, 2017 5.0 Having a true view of the numbers on all levels of the business. Pros They've made reporting very simple to really dive into the numbers. The inventory side of things has made it a breeze to keep track of inventory as a great feature is costs vs landed costs. Cons They online feature is outdated and not mobile friendly for today's marketplace. The actual software would be great to have availability for web based. Review Source EW Ed W. Partner Retail Used the software for: 2+ years ### "Using Windward in a Small Shop" January 26, 2021 5.0 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. Review Source EH Edith H. Owner/operator Retail Used the software for: 2+ years ### "Yes you can enter the computer age!" July 6, 2022 4.0 Pros My existing business had an old time cash register when I purchased it. At the beginning 12+ years ago it worked ok for me. But over the years as prices rose. I had no way of knowing at a glance what I paid for an item and what I should be selling it for. I was losing money! I was familiar with another accounting system but it required extensive time at home each night entering hand written A/R bills and daily till totals into its system so I could bill customers. I had heard of Windward several years prior but just didn't think I could afford it. A new employee who had experience with other systems encouraged me to purchase. Implementation was so much work because I didn't have any inventory computerized. No lists and I jumped in in the middle of a month and a fiscal year. I was going to finance the purchase over 2 years but decided to put it on my line of credit. I paid it and my new equipment off in 6 months! I have now used the software for 7 years and am very happy with it. It has saved me about $2000.00/year in accountant fees. Love the fact that all monthly Provincial and Federal sales tax reports are easily paid. It has an employee section with payroll etc. So easy to upload inventory that is new from an excel spreadsheet. Cons Inventory from multiple suppliers with barcodes have to be entered in as coming from one main supplier with all other suppliers entered in as alternates. The barcode can't have any supplier attached to it or my computer makes a loud beep. I purchase by item # not by barcodes. I wish the system would let you enter item #'s from each supplier with the corresponding barcode even if it is also the same barcode for another supplier. I am not always aware that the product coming from one supplier is already in my system under a different supplier. Switched from [QuickBooks Desktop](https://www.capterra.com/p/212058/QuickBooks-Desktop-Pro/) My employee's recommendations Review Source Response from Windward Software August 9, 2022 Thanks Edith, We're glad that you've gotten so much value out of the software! You might benefit from a Business Efficiency Check-In since you've been with us so long. It is a paid service where we review how you're using the software and if there's anything that's changed since you started. Well worth it, especially if we find a few more things that could save you time and money. Talk to your account manager to get started. Thanks again! CM Colin M. Inside Sales and Marketing Automotive Used the software for: 2+ years ### "I depend on Windward every day for my role in sales and marketing. I couldn't do my job without it!" November 11, 2017 5.0 It's integral to my role in the company. In fact everyone in our company uses Windward on a daily basis. We use it in every aspect of our product based business from order processing, to sales, management, warranty, accounting and inventory management. Pros I like the ability to generate custom sales reports so I can see who my top dealer accounts are, and which accounts I need to incentivize. I need to quickly check stock of products in all four of our warehouse locations, and when a product is out of stock, I need to be able to quickly see what's been ordered and when we are expecting it to arrive at our warehouses. In a "just in time delivery" business world like ours, giving customers an accurate ETA can mean the difference between closing the sale and not closing it. As a sales manager, I like to look at what the top selling products are by customer and by regions. I like to review our sales trends month by month and year by year, and see where we need to improve. I also need to see the full financial picture of sales, cost of goods sold and company expenses, to make sure we continue to run a streamlined operation and remain competitive in a constantly changing marketplace. Windward's reporting features are excellent in this regard. Windward is an extremely powerful and feature packed program. It does everything we need to run our business, from accounting to sales; order processing to invoicing; warranty claims and product returns; and generating reports that all levels of management can use to efficiently run their department, or the whole company. In summary, Windward is an extremely comprehensive program that is well suited to our product-based business. Cons Like any feature packed program, intuitive menus are critical to accessing all the nuances of the software. Most of power software programs leave something to be desired in the area of intuitive interfaces. Windward is no exception to this. Thus, task specific training modules and quick customer support is of utmost importance to users being able to shorten the learning curve when expanding their knowledge of Windward. Review Source LL Larry L. Purchaser Mining & Metals Used the software for: 2+ years ### "WIndward: A decent database for small business. (Version: 6.2.4.579)" June 27, 2022 4.0 Overall, Windward is stable and fairly simple to use. The product also includes a rental component which is also fairly simple to operate. Pros Ease of use, Windows familiarity help to make a decent experience. Cons Too many times, brushing a hand over the keyboard has erased entire lines from the invoice. An invoice locking tool would be great. Review Source Response from Windward Software August 9, 2022 Hi Paul, Thanks for the feedback and for choosing Windward System Five for your business. If you want to review some of the specifics you mentioned, please reach out to your Account Manager. MD Madison D. PURCHASER Retail Used the software for: 2+ years ### "Honest Thoughts " June 27, 2022 3.0 This system is chalk full of great concepts but it always falls short of our needs. The band-aids given for our issues are never a resolution, just a temporary fix and often more work. System Five does work, it crashes every few months but overall we can continue with business. We will continue with System Five. Pros There are many features that could be incredibly useful. The reports have vast options which we utilize often. Cons It seems every update an equal amount fixed gets broken. We always seem to be chasing down issues and fixing bugs. There is not one week we do not have issues in our system, user or system error. Every feature seems to tap out in functionality. They all have an amazing idea, but when we try to use them there is always a reason it does not work for our system or with our data. Review Source Response from Windward Software August 8, 2022 Thanks for the fair feedback Madison, We're working on some new automated testing that will reduce the number of defects going forward. We'd be happy to review some new reporting options that might be helpful. Please reach out to your Account Manager if you'd like to set that up. LJ Laura J. Corporate Secretary/Business Manager Retail Used the software for: Less than 6 months ### "This system is not worth the money, time, effort with no support" April 3, 2022 1.0 Windwards Systems INC gave a great sales pitch and were recommended by our Marketing Partner Spectra. Unfortunately, I should have researched their reviews better prior to spending a lot of money and 4 months of frustration with the implementation of the new system. I had really hoped we could integrate our Lights America system with Windward Systems as promised. However, the issue was reported at the beginning of February to their IT Support. After 2 months of not being resolved, us unable to go further in the implementation and being told only one (1) support person could resolve this issue in their company! Not to mention that one (1) IT support person worked night shift and would call us at 9:00 pm Eastern Time for us to login the system so he could troubleshoot! Are working hours are 8:00 am to 4:30 pm. That was just one issue. The other issue was moving our information from our old software to the new software. We were requested to provide them with spreadsheets of the information to upload. We paid our current IT Support to pull all the spreadsheet and I sent them to Windward only to be told the setting up of the spreadsheets from our old system to Windward was "a lot of work" My question to them was "a lot of work for you?" or "a lot of work for me?" The answer was for me to send the the spreadsheets after setting them up and work 40 + hours attending to my business. I feel that for the amount Windward was costing, their IT Support should have taken the "work" on them Pros It seemed easy to use. Seemed easy to set up. Seemed to do everything I would need to run POS, Inventory, Payables and Accounting. Cons Lack of IT Support. Please read my experience. Reason for choosing Windward System Five I choose Windward because it was recommended by the Spectra Marketing Group which we are a member of. Also, Windward is supposed to integrate with Lights America our website builder. Review Source Response from Windward Software April 18, 2022 Thank you for taking our call and allowing us the opportunity to get you Live on Windward Software. NS Nicole S. Finance Administrator Used the software for: 2+ years ### "Windward can't do that, but let's try to come up with a "Workaround" for you...." October 30, 2017 2.0 Headaches Pros I like the ability to special order a product on a work order and have it directly linked to the purchase order. Great for tracking an item through. Cons INVENTORY!!!! There is no direct link between the inventory sub-ledger and the ledger. There is no transaction list of what is recorded in the sub-ledger, so balancing inventory and determining where an outage may have occurred is a long, tedious process that involves tracking every purchase order received, bill, work order and invoice put into the system. Implementing the software is very time consuming and self-regulated. Enhancements to the software can be requested if your company agrees to pay for the programming time to develop it. Review Source Response from Windward Software November 3, 2017 Hi Nicole. Thank you for taking the time to provide your feedback with regards to Windward System Five. Glad to hear that you are finding our Special Order Tracking feature useful; it's a popular one among many of our clients. In terms of your concerns, upon review, it appears that there are, in fact, methods of solving some of the issues you are experiencing through existing product functionality. We encourage you to contact your Account Manager at +1 (800) 663-5750 to become registered for The Windward Learning Academy. This comprehensive online resource of easy-to-use product tutorials clearly demonstrates the most efficient means to use System Five by feature and scenario. In addition, we value your feedback in terms of custom enhancements. In some cases, with requested enhancements that only pertain to a very small subset of our clients, at least a portion of this development work may be billed. Widely beneficial enhancements are completed in future releases at no fee. WG William G. Controller Wholesale Used the software for: 2+ years ### "Review - Windward System Five" June 27, 2022 5.0 System is basically garbage in - garbage out, meaning if you provide correct data, it will give you accurate information and results. Pros User friendly. POS system. A/R and A/P system. Inventory system. Financial reporting. Cons No complain at all. System integration was smooth and encountered no problems. Reason for choosing Windward System Five One stop shop for all our needs! Review Source PG Pete G. Used the software for: 6-12 months ### "This is NOT a Rental Software" February 17, 2017 1.0 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 Review Source mK mike K. Owner/ President Retail Used the software for: 2+ years ### "Garbage in Garbage out. This program is great, but you have to put in the time or resources to put in all the information and take time to set the switches." November 29, 2017 5.0 my sales person has been very helpful. Even though I really complained to him when I had to upgrade the pervasive side of Windward. It was not that much, but as a business owner, I felt like everyone has there handed out to collect money. This is not Windwards fault, I had not upgraded pervasive in awhile and really did not know I had to. When my business burned in May of 2016 I had the backups but the three backups where all in the building. I dug through the debris and found the server and windward did not ask for any money to help me get the information back uploaded. I did not have a support package at that time and they could have asked me to upgrade the software and pay for a support package. Windward did not ask me for any money at all. Their technical department spent about 3 hours with my computer guy getting the information linked back up because some of the files where lost. I got locked out of the system and windward again helped me get back in. Thanks again Windward. Mike Kernea owner of Skyline Power Equipment Pros What I mean by the switches. This program allows you to set up the program the way you want it. It does have a default setting, but I have found that each company is different and require certain information. When sitting up the program go somewhere quiet with no distractions. Also if the program does what you want it to you do not have to upgrade. Cons If you don't upgrade then it is very hard for the company or technical support to help because they are running on another version. Review Source HA Heather A. owner Retail Used the software for: 2+ years ### "why I use windward" June 21, 2022 4.0 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. Review Source MS Mario S. IT Manager Used the software for: 2+ years ### "Very flexible, comprehensive software package with a somewhat cumbersome user interface." October 25, 2017 2.0 Pros the flexibility thanks to various data load and import options, the ability to chain import/exports and call external scripts; detailed permission settings; the numerous features; lots of customisable reports easily ported to spreadsheet or similar. Cons \- documentation is very fragmented, incomplete and sometimes just wrong. - the user interface is not intuitive and a long way from modern apps. I couldnt convince our sales team to use the tasks/appointment/history-comments section as they found it too complex (but feature wise I think it's good). - the one time we needed support, we received bad advise which would have crippled this company if it had been followed. - a selection of sample scripts would really help with implementation of more complex customisations. - the unique email feature is applied across both suppliers and customers. this is problematic where a customer is also a supplier. - no support for linux pervasive engines any more. - no support for Sys5Script.exe any more. - the template editor is very unpleasant to use. Very tricky to create a visually pleasing document. Review Source KD Karen D. Owner Used the software for: ### "13 years with System 5" June 1, 2016 5.0 I installed System 5 for my "brick and mortar" business in 2003. This is one of the best investments I have made for my business. I have thousands of parts & customers, and hundreds of suppliers. Most of my inventory is tracked by serial number. "Windward" is pretty quick in spite of my huge database, and the interface makes it very easy to look up info (such as customer past purchase history, showroom display serial numbers, etc). I've had great phone support when updating to newer releases, migrating the application from old servers to newer servers. Their support team has patiently even helped me through accounting questions. Once, my whole system was completely dead because my tech support guy did something on the server, and WW resolved it right away. For me, a key capability is being able to import and export information easily into and out of Excel, so that I can maintain pricing for so many parts from many suppliers. I also use Excel for sales analysis and budget reports (outside of WW), so we can "slice and dice" the data (13 years worth) to analyze leading indicators of sales trends, for example. Since work orders can be populated from an external data file, I've created an external visual interface to create the work order line items for our more complex customer configurations, and have them load automatically into a work order. After 13 years, I have a laundry list of things I would like to see added or changed in the system. However, reliability and dependability are my top priorities and on that front, WW has been excellent. Windward returns calls, answers questions, owns up if the issue is on their end, finds acceptable temporary workarounds, and makes me feel that my business success is important to them. They do NOT create barriers to communication, throw up brick walls ("that's just the way it is"), or tell me I'm running my business the wrong way ("most of our customers don't change their prices just because their costs change") - which I have actually experienced with other software vendors. During implementation, I designed my categories to support the ways I wanted to be able to analyze the data in both WW and in Excel. If you don't have any software background, I would strongly recommend working with a reseller/design consultant for the initial layout and installation (which I think would be true for any accounting system), because that will set you up for success going forward. Review Source RD Ronald D. Controller Used the software for: 1-2 years ### "I have been using Windward System 5 as the Financial Controller for about 18 months" November 14, 2017 3.0 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. Review Source Response from Windward Software February 26, 2018 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. JK Jonathan K. Sales & Service Manager Wholesale Used the software for: 2+ years ### "Great fitting package for our business" July 19, 2022 5.0 System Five has been very good, and their support team is excellent and helpful Pros Windward fits us great, the cloud system was a very important consideration for remote accessibility. It covers all of our needs in terms of sales, repair work orders, and inventory controls. It is just the right amount of software for us. Cons There are some advance features that could add value for us, such as stock adjustments that post to G/L's, min/max's that make recommendations on PO's Review Source Response from Windward Software August 9, 2022 Hi Jonathan, Thanks for the review. You may want to look into the advanced features, they really can be a time saver. Professional Services are available to help you get those implemented. Have a convo with your Account Manager if you'd like to consider that option. Thanks again! ## 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. Talk to a Capterra advisor for free and get results within 15 minutes.