--- title: "Windward System Five Reviews, Pros and Cons - 2026 Software Advice" description: "Reviews of Windward System Five. Learn how real users rate this software's ease-of-use, functionality, overall quality and customer support. Talk to our advisors to see if Windward System Five is a good fit for you!" source_url: "https://www.softwareadvice.com/retail/windward-system-five-profile/reviews/" page_type: "reviews" language: "en" --- 1 million+ businesses helped. Get advice Get Free Advice [Home](https://www.softwareadvice.com/) / [Retail Management Systems Software](https://www.softwareadvice.com/retail/retail-management-comparison/) / [Windward System Five](https://www.softwareadvice.com/retail/windward-system-five-profile/) / Windward System Five Reviews Software Advice offers objective insights based on verified user reviews and independent product and market research. When our advisors match you to a software provider, we may earn a referral fee. [Overview](https://www.softwareadvice.com/retail/windward-system-five-profile/) Reviews [Alternatives](https://www.softwareadvice.com/retail/windward-system-five-profile/alternatives/) # Windward System Five User Reviews ## Reviews summary - Overall rating: 3.8/5 - Total reviews: 189 ### Secondary ratings - Ease of use: 3.7/5 - Customer support: 3.7/5 - Value for money: 3.6/5 - Functionality: 3.8/5 ### Rating distribution - 5 stars: 71 reviews (38%) - 4 stars: 64 reviews (34%) - 3 stars: 20 reviews (11%) - 2 stars: 15 reviews (8%) - 1 star: 19 reviews (10%) ### Most mentioned pros - It is a different system but once you get to know it and set it up for your business requirements it sets it apart from quickbooks and other accounting software. - My overall experience was positive, and still is to some extent, though we largely use System Five as a database for older customer information now. - We do very much like the additional features such as inventory management, price checks/updates, but have trouble at time keeping it current due to staffing issues. ### Most mentioned cons - Very difficult to move away from - their database structure is as well thought out as a dump truck full of spaghetti. - Very expensive - literally 22.5 TIMES the cost of the software we tried to replace it with. - not clover integrated- they can't figure out how to get my statements mailed out of the system to clients properly. ## Windward System Five customer reviews Showing reviews 1-25 of 189 (page 1). ### Windward review - Overall rating: 5/5 - Reviewer: April T. - Verified reviewer: Yes - Industry: Consumer Services - Company size: 11-50 employees - Product usage: Used daily for more than 2 years - Reviewed: June 2022 - Review source details: This reviewer was invited by the software vendor to submit an honest review and offered a nominal incentive as a thank you. Well built system that covers a lot of different types of business. #### Ratings breakdown - Ease of use: 5/5 - Value for money: 4/5 - Customer support: 5/5 - Functionality: 5/5 #### Pros Unlimited features . Can do so much with a split business that we run. #### Cons Would like to have more form creation options --- ### Great system management - Overall rating: 5/5 - Reviewer: Nava C. - Verified reviewer: Yes - Industry: Building Materials - Company size: 2-10 employees - Product usage: Used daily for more than 2 years - Reviewed: July 2022 - Review source details: This reviewer was invited by us to submit an honest review and offered a nominal incentive as a thank you. When we first took over this long-time local business, previous owners did most reports or tracking by hand (ie hand-written invoices entered into QB and hand-written price books) WWS5 helps us keep track of items in inventory, current prices and mark-ups for inventory, general price increases from vendors, EOD reports and sales, and AR accounts much more easily. We do not currently use the accounting portion, but hope to move over to the accounting option with the new data set. #### Ratings breakdown - Ease of use: 4/5 - Value for money: 4/5 - Customer support: 5/5 - Functionality: 5/5 #### Pros We currently use Windward for our POS and AR needs. This helps keep us on track for monthly billing to AR clients and keeps up with the daily till. We do very much like the additional features such as inventory management, price checks/updates, but have trouble at time keeping it current due to staffing issues. With more staff, this system would be absolutely amazing. #### Cons When we first installed Windward, there were issues with understanding the larger picture during set-up. Understanding more about the system prior to set up would have helped. We are currently setting up a new database now that we understand more about the full operation of WWS5. #### Reasons for choosing Windward System Five Other POS options were too simplistic for our needs tracking hardwood lumber bought & sold by the board foot. WWS5 allows us to use the Z sheet to calculate board footage much more quickly when checking out customers and was not as expensive as other lumber yard systems. --- ### Windward System 5 has made running our medium sized dealership much easier - Overall rating: 5/5 - Reviewer: Trish H. - Industry: Retail - Company size: 11-50 employees - Product usage: Used daily for more than 2 years - Reviewed: October 2017 - Review source details: This review was submitted organically. No incentive was offered Time and inventory management equals money savings #### Ratings breakdown - Ease of use: 4/5 - Value for money: 4/5 - Customer support: 5/5 - Functionality: 5/5 #### Pros The point of sale system gives real time inventory tracking and the integrated accounting system saves hours of time each week #### Cons The software is almost too in depth especially for users who are not computer savvy or who have a hard time learning new systems --- ### We couldn't live with our our System 5 - Overall rating: 5/5 - Reviewer: Kathi M. - Verified reviewer: Yes - Industry: Retail - Company size: 2-10 employees - Product usage: Used daily for more than 2 years - Reviewed: June 2024 - Review source details: This reviewer was invited by the software vendor to submit an honest review and offered a nominal incentive as a thank you. We couldn't do without them and their service is fantastic. #### Ratings breakdown - Ease of use: 4/5 - Value for money: 4/5 - Customer support: 5/5 - Functionality: 4/5 #### Pros How the inventory management and purchasing work. So many extra features here that make it so helpful. #### Cons How the form creation functions. It is a difficult process and way too time-consuming. #### Reasons for choosing Windward System Five We couldn't find any other software back in 2005 that would do order entry and point of sale all in one and hold as much inventory as we need. Windward was the only one at that time that was affordable. #### Reasons for switching to Windward System Five We had proprietary software written for out company. Our computer guy didn't want to support his program any longer. We used it in conjunction with Quick Books Pro. #### Vendor response Thanks for your review! We're sure it will help a business owner make the right call by switching to Windward Software. Replied September 2024 --- ### Windward Review - Overall rating: 4/5 - Reviewer: Derek S. - Verified reviewer: Yes - Industry: Retail - Company size: 11-50 employees - Product usage: Used daily for more than 2 years - Reviewed: June 2022 - Review source details: This reviewer was invited by the software vendor to submit an honest review and offered a nominal incentive as a thank you. Mostly positive when it comes to day to day interaction. Any negatives are more nit-picking issues. #### Ratings breakdown - Ease of use: 4/5 - Value for money: 4/5 - Customer support: 5/5 - Functionality: 2/5 #### Pros Required Orders system and ability to interact with the invoice easily throughout. #### Cons Lack of multiple kits. Purchase orders with SO items become buggy with large quantities. If a user moves too quickly in the system, it can break. #### Reasons for choosing Windward System Five Price and size of the business did not warrant its need. #### Reasons for switching to Windward System Five Needed inventory management, the option for more departments --- ### FIX MOST ANY THING..FOR A COST - Overall rating: 3/5 - Reviewer: Jeff G. - Verified reviewer: Yes - Industry: Automotive - Company size: 11-50 employees - Product usage: Used daily for more than 2 years - Reviewed: April 2024 - Review source details: This review was submitted organically. No incentive was offered #### Ratings breakdown - Ease of use: 3/5 - Value for money: 3/5 - Customer support: 1/5 - Functionality: 3/5 #### Pros The system has many good functions and tracking abilities. #### Cons Had to have a "wildcard" search for part numbers programmed in after they said it wasn't part of the system. It was already in the system for description but not for parts. As like so many other reviews, updates are a roll of the dice to see what will be affected when they are done. The biggest issue is, A PRICING MATRIX WITH VARIABLE RATES BASED ON COST. Currently I can set up different percentages based on supplier, sub category and others, BUT I am unable to set a pricing matrix with varying percentages for an increasing cost value. That is $1.00 may be marked up 300% but $1000.00 isn't. 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. I was told we could spend more money to have some one talk to us to tell us they don't know how to do this. The irony of it all is that I came from a Winworks System that we were out growing, but it had that function available to a great extent. Again kudos to the sales team for saying this system could do every thing we first questioned. #### Reasons for switching to Windward System Five Was promised Winward could do every thing we needed. #### Vendor response Thanks for your feedback. We appreciate customer input like yours to help improve our software solutions and services. We are committed to fixing defects (bugs) that cause errors in our solutions at no extra charge for our customers. This has been our standard practice for over 40 years. We've assessed the complex pricing matrix you described in your feedback and understand that the requirements include varying percentages based on increasing cost tiers for parts. As you mentioned, this functionality does not exist in System Five and it is complex to build. Our Custom Development Services are designed to fulfill a request like this. We will build or enhance a solution to suit your unique needs. Yes, this type of custom work is a billable service. We encourage you to have a conversation with your Windward Account Manager for more information and to arrange for a consultation if this is important to your business. Our team is here to serve you and support your growth and success. Replied May 2024 --- ### continuing forward - Overall rating: 2/5 - Reviewer: Bob N. - Verified reviewer: Yes - Industry: Furniture - Company size: 2-10 employees - Product usage: Used daily for less than 2 years - Reviewed: June 2022 - Review source details: This reviewer was invited by the software vendor to submit an honest review and offered a nominal incentive as a thank you. We are continuing to use System Five as migration is a challenge for a small business like ours. The support crew at Windward work well to address issues; however, our account manager failed to address items that were still in process just prior to go live. Those items remain outstanding as support is unable to address them. #### Ratings breakdown - Ease of use: 1/5 - Value for money: 2/5 - Customer support: 4/5 - Functionality: 2/5 #### Pros Immediate processing of credit card transactions. The fact that System 5 is in the cloud is one of the primary reasons we purchased the product. #### Cons Not enough explanation of defaults in System 5 caused redundancy in our chart of accounts. The monthly reconciliation requires that several routines be performed before you can have a reliable balance report of income/expense reports. Modifiers were disappointing as we learned that they must be setup on an item-by-item basis, rather than a category or brand basis. Custom reporting is extremely lacking and doesn't allow for us to produce the reports we need. #### Reasons for choosing Windward System Five The combination of financial and pos into a single application. The demos we went through for home furnishing solutions. Modifiers and their usage were also a primary reason we chose System 5. We found out after commitment that the modifiers would not work in our shop. #### Reasons for switching to Windward System Five The apps were on-prem based. We wanted a Cloud based solution. We thought the combination of a financial app and POS app would make things work smoother. --- ### Windward Software is an amazing program to help you run your business in every aspect. - Overall rating: 5/5 - Reviewer: Rossie F. - Verified reviewer: Yes - Industry: Retail - Company size: 2-10 employees - Product usage: Used daily for more than 2 years - Reviewed: June 2022 - Review source details: This reviewer was invited by the software vendor to submit an honest review and offered a nominal incentive as a thank you. Inventory was a huge issue for us before we started using System Five. We absolutely cannot imagine running our business without Windward System Five at this point. #### Ratings breakdown - Ease of use: 5/5 - Value for money: 5/5 - Customer support: 5/5 - Functionality: 5/5 #### Pros The Support is A1 and the features of everything from Inventory to Sales Invoices, everything is connected and very user friendly. Reports are easy to run, reconciliations, sales and purchase invoicing, ageing, financials are easy to read and all other functions are again, user friendly. #### Cons No cons at this time. We didn't like that it didn't have a payroll feature when we started with it but now it does. #### Reasons for choosing Windward System Five When we were given a demonstration, we knew right away it could handle what we needed and more. #### Reasons for switching to Windward System Five We didn't like their Inventory feature or their GL postings that you could never correct even if it wasn't reconciled. --- ### Tami McQuown - Overall rating: 4/5 - Reviewer: Tami M. - Verified reviewer: Yes - Industry: Recreational Facilities and Services - Company size: 11-50 employees - Product usage: Used daily for less than 2 years - Reviewed: June 2022 - Review source details: This reviewer was invited by us to submit an honest review and offered a nominal incentive as a thank you. Its been a great experience! #### Ratings breakdown - Ease of use: 3/5 - Value for money: 4/5 - Customer support: 5/5 - Functionality: 3/5 #### Pros Ease of use, technical support answers all questions #### Cons Credit card transactions did not go well at first #### Reasons for choosing Windward System Five A true POS system #### Reasons for switching to Windward System Five Needed more features, all in one, a true POS system --- ### Slightly outdated, but intuitive and powerful - Overall rating: 4/5 - Reviewer: Mason B. - Verified reviewer: Yes - Industry: Consumer Goods - Company size: 2-10 employees - Product usage: Used monthly for less than 2 years - Reviewed: August 2025 - Review source details: This reviewer was invited by us to submit an honest review and offered a nominal incentive as a thank you. My overall experience was positive, and still is to some extent, though we largely use System Five as a database for older customer information now. Searching for historic records of customer purchases, inventory tracking over time, and loyalty program points still works very well. #### Ratings breakdown - Ease of use: 4/5 - Functionality: 4/5 #### Pros Good value, and capabilities of software were far more advanced than I was expecting. Capable with inventory tracking, private customer data management, and invoicing. #### Cons 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. --- ### WindWard System 5 for Business - Overall rating: 5/5 - Reviewer: Shauna H. - Verified reviewer: Yes - Industry: Retail - Company size: 11-50 employees - Product usage: Used daily for more than 2 years - Reviewed: November 2024 - Review source details: This reviewer was invited by the software vendor to submit an honest review and offered a nominal incentive as a thank you. It has been great learning a new system and tailoring it to the needs of my bosses and the business. The learning I have been able to gain from the videos and training I attended have helped. #### Ratings breakdown - Ease of use: 3/5 - Value for money: 3/5 - Customer support: 3/5 - Functionality: 4/5 #### Pros It is a different system but once you get to know it and set it up for your business requirements it sets it apart from quickbooks and other accounting software. It is more POS friendly. #### Cons The bugs that can happen where the system is not updating correctly. The system is more POS friendly than accounting friendly. If you do not learn about the system, it can mess up the information more so there needs to be better training especially for the older users that have been using the system for a long time. --- ### From your friends at Bob's - Overall rating: 5/5 - Reviewer: Justin S. - Verified reviewer: Yes - Industry: Retail - Company size: 2-10 employees - Product usage: Used daily for more than 2 years - Reviewed: April 2022 - Review source details: This reviewer was invited by the software vendor to submit an honest review and offered a nominal incentive as a thank you. Windward 5 does so much above and beyond the POS/accounting systems I have used in the past, and I know I haven’t made it through all it has to offer. The integrated CRM is very useful for keeping track of appointments and follow ups. I’m able to see that staff has made these appointments and keep them accountable for follow ups. There is so much that can be done to organize and track inventory. Set multiple selling prices, build kits out of existing parts. Add pictures for staff and customers to reference, and way more. Booking orders use to take me days to put together. Now the system tells me what I need based on past years. Some orders now take me less then a hour. Information and automation. Windward tracks so much for you and automates tasks. Saving you 100’s of hours and $1000’s of dollars a year. I am very happy I made this investment #### Ratings breakdown - Ease of use: 4/5 - Value for money: 5/5 - Customer support: 5/5 - Functionality: 5/5 #### Pros Windward 5 does so much above and beyond the POS/accounting systems I have used in the past, and I know I haven’t made it through all it has to offer. The integrated CRM is very useful for keeping track of appointments and follow ups. I’m able to see that staff has made these appointments and keep them accountable for follow ups. There is so much that can be done to organize and track inventory. Set multiple selling prices, build kits out of existing parts. Add pictures for staff and customers to reference, and way more. Booking orders use to take me days to put together. Now the system tells me what I need based on past years. Some orders now take me less then a hour. Information and automation. Windward tracks so much for you and automates tasks. Saving you 100’s of hours and $1000’s of dollars a year. I am very happy I made this investment #### Cons It does take some time to set up, but you do get some great help. There is allot to learn. Be prepared to give this some attention, it will be worth it. #### Vendor response Thanks for the Feedback Justin! Replied April 2022 --- ### Amazing POS system that can be intergrated with payroll - Overall rating: 5/5 - Reviewer: Stephine B. - Verified reviewer: Yes - Industry: Automotive - Company size: 2-10 employees - Product usage: Used daily for more than 2 years - Reviewed: July 2022 - Review source details: This reviewer was invited by us to submit an honest review and offered a nominal incentive as a thank you. It is a great software company and always willing to help and easy to access if there is a problem. #### Ratings breakdown - Ease of use: 5/5 - Value for money: 5/5 - Customer support: 5/5 - Functionality: 5/5 #### 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. #### Reasons for choosing Windward System Five When checking other products we felt this was the best system to meet all our needs and the best price as well. Liked that we could integrated our debit/credit card machine as well as payroll. #### Reasons for switching to Windward System Five Tman was a dos based program and we need to upgrade. We felt that this was the best system for us. Had a consultant help us with the setup until we were ready to go live. --- ### System Five - Overall rating: 3/5 - Reviewer: Derek M. - Verified reviewer: Yes - Industry: Retail - Company size: 11-50 employees - Product usage: Used daily for more than 2 years - Reviewed: June 2022 - Review source details: This reviewer was invited by us to submit an honest review and offered a nominal incentive as a thank you. Service and online capability was not good. While we paid for 24/7 service, we had to setup tickets and would get a call back within 24hrs. #### Ratings breakdown - Ease of use: 4/5 - Value for money: 2/5 - Customer support: 1/5 - Functionality: 3/5 #### Pros The built in reports allowed for easily customizing reports. With their "lookup words" it was easy to tag, customers, products and vendors to particular categories for additional reporting #### Cons The online capability. There was no good capability for online. Sales would take a long time to integrate back into the software and there was no direct connection between Windward S5 to the online platform such as WooCommerce. Which meant an additional cost for another API connection. Windward API was very limited to what info could be pushed and pulled from the website. #### Reasons for switching to Windward System Five We outgrew the software #### Vendor response Hi Derek, Thanks for the feedback. In recent months we've launched the new WebSell integration and have enhanced our WooCommerce connector in an effort to get more of our customers online. This no longer relies on an API. Please reach out to your Account Manager to explore options. Replied August 2022 --- ### Windward- Success for Power Equipment, Construction Supplies and Rental - Overall rating: 5/5 - Reviewer: Jim P. - Industry: Retail - Company size: 11-50 employees - Product usage: Used daily for less than 6 months - Reviewed: January 2017 - Review source details: This review was submitted organically. No incentive was offered We have been using System 5 since 2003. The system has scaled to our operation as we grow. The accounting side is robust and handles all our AP- AR- and General Ledger needs. Purchasing is fully automated. Billing customers can be fully modified with "Types" and "subTypes" to keep the status of orders updated and classified. Our inventory and product locations have been controlled and managed with the Advanced Inventory Control. The system is constantly being improved with fixes and new features multiple times per month. The database is rock solid. After 14 years, we never have had data corruption requiring the loading of a backup. All our employees depend on the info from system 5 to make decisions and give customers information. The ability to customize and provide information to users is endless and grows each year. We have used the barcode function and have 40,000 SKUs barcoded and labeled. We have even barcoded our rental equipment. We rely on this system for everything and for 14 years it has been bulletproof. Because we sell, service and rent serialized equipment, the "UNIT" way of handling things is great. Provides cost, service and income information. #### Ratings breakdown - Ease of use: 5/5 - Value for money: 5/5 - Customer support: 4/5 - Functionality: 5/5 #### Pros We could not run our business without the information and order that the system provides! 1. Ease of use- Everything is in one program 2. Total integration- We don't need to transfer data to another program like QuickBooks 3. Strong Accounting, Control, and reports- Ability to customize GL and P&L format and multiple years. 4. Hundreds of pre-built Reports- We rarely do custom 5. Ability to create custom reports 6. Barcoding and Barcode printing- Couldn't live without it 7. Integrated Credit card Processing-Vantiv- Saves errors and time 8. Moves easily from desktop to desktop - configures easily when replacing stations 9. Weekly online training to learn features. 10 Responsive support staff who find the answers to any questions. 11. Ability to attach pictures and documents. 12. Unit history on serialized items. 13. Automated output of data, pictures pricing and descriptions to our Website #### Cons Probably not really a con But there are so many features available, it take some time to learn and put them into daily practice. The rest are just enhancements we'd like to see !! First, We would like to see the RMA system simplified. Second, we would like to see the E-commerce platform developed more. We are using it now for our website, but we would like to see more features and search options. Third, we would like to see the Timecard function developed and enhanced. Fourth, we would like to see the offering of more credit card processing options. Fifth, we would like the ability to attach PDF's to items, instead of JPG. But all in all, the system works really well! --- ### Gets the job done. Do not do the updates. - Overall rating: 3/5 - Reviewer: Teegan M. - Product usage: Used daily for more than 2 years - Reviewed: November 2017 - Review source details: This review was submitted organically. No incentive was offered #### Ratings breakdown - Ease of use: 4/5 - Value for money: 2/5 - Customer support: 3/5 - Functionality: 3/5 #### Pros Very thorough software with lots of room/areas to store Information and very easy to use. The point and click ability of the software makes it easier to train new staff. Can access the software from anywhere in the world using remote desktop connection. #### Cons The updates do not seem to go very smoothly. And update me fix one problem but two new problems arise that were not problems before. We have actually stopped getting updates and have continued to use our current version for years. We have developed our own internal ways to use the software to its fullest potential without getting updates. Software support is readily available however very expensive and a lot of the problems that we have encountered do not have the solution. In order to get the solution we have to pay for the entire resource development team and have to be very very patient to see results. The yearly license fee does not benefit our company as we do not complete the updates. So we paid the fee however are using an out of date software program Because we are afraid to update. Phoning for tech-support can be quite challenging when the bill is charged per minute and we are on hold for 80 percent of the call. We are usually on hold while the tech support discusses with superior or development team to solve our more complex problems. At the end of the day the software program helps us maintain our current business but is not helping us grow our business. We are not ready to commit thousands of dollars to the software program that still has many issues even if we were to update to most current version --- ### Tricky to learn but works well once mastered. - Overall rating: 4/5 - Reviewer: jamie v. - Verified reviewer: Yes - Industry: Consumer Goods - Company size: 2-10 employees - Product usage: Used daily for more than 2 years - Reviewed: June 2022 - Review source details: This reviewer was invited by us to submit an honest review and offered a nominal incentive as a thank you. Positive, but can be frustrating when it errors. #### Ratings breakdown - Ease of use: 2/5 - Value for money: 3/5 - Customer support: 4/5 - Functionality: 3/5 #### Pros Inventory management, help centre, payroll is straight forward. #### Cons Sometimes it can be glitchy. Example, sending a paystub to the wrong employee, in clearing an item for years ago, just weird random error messages. #### Reasons for choosing Windward System Five Inventory and customer care help centre reviews. --- ### Windward - Overall rating: 3/5 - Reviewer: Tania K. - Verified reviewer: Yes - Industry: Hospital & Health Care - Company size: 11-50 employees - Product usage: Used daily for less than 2 years - Reviewed: June 2022 - Review source details: This reviewer was invited by us to submit an honest review and offered a nominal incentive as a thank you. I am finding as time goes by, there are better ways to do things. There is a lot of potential however I was not shown this at the start of the switch over. It makes it harder to change things after 6 months. #### Ratings breakdown - Ease of use: 4/5 - Customer support: 4/5 - Functionality: 3/5 #### Pros System is easy to use when you know what you are doing. There is much potential. #### Cons Proper training was not given at the beginning as to what would be beneficial most to our business. I had to use training videos to learn how to do things. Limited search module. #### Vendor response Hi Tania, Switching systems and that initial learning phase can be difficult. We're always reviewing and making adjustments to how we handle implementation and training. If you are still feeling unequipped, please reach out to your Account Manager to go over both included and paid training options. Replied August 2022 --- ### Our experience with Windward - Overall rating: 4/5 - Reviewer: Nannette L. - Verified reviewer: Yes - Industry: Maritime - Company size: 2-10 employees - Product usage: Used daily for more than 2 years - Reviewed: June 2022 - Review source details: This reviewer was invited by us to submit an honest review and offered a nominal incentive as a thank you. #### Ratings breakdown - Ease of use: 4/5 - Value for money: 4/5 - Customer support: 4/5 - Functionality: 4/5 #### Pros Customer service is very quick to get back with us and make sure that we are taken care of. #### Cons Having to buy hours for pricing updates and having them expire before all our vendors print their new pricing. #### Reasons for choosing Windward System Five We chose Windward for its ability to handle the 10s of 100s of part numbers we use. --- ### Scalable multi-user POS retail from a company that listens and adapts. - Overall rating: 5/5 - Reviewer: Mike R. - Industry: Retail - Product usage: Used unspecified for more than 2 years - Reviewed: June 2015 - Review source details: This review was submitted organically. No incentive was offered #### Ratings breakdown - Ease of use: 5/5 - Customer support: 5/5 - Functionality: 4.5/5 #### Pros Excellent customer support 24/7. A product that is scalable to your business. One of the few softwares that have a stand-a-lone ability that allow sales and lookup when the main server is offline or unavailable. Inventory orders in cases or singles by multiple suppliers with multiple part numbers and UPC codes for a single item. Capable of printing price tags on the fly when receiving. Easy lookup of products at the POS terminal by description, barcodes, serial numbers, etc. (Think about a phone caller asking for an item that is not in your hand, no numbers available and you need to quote the price.) Easy Purchase ordering. Easy resorting of POs in a fashion that matches the packing list. Complete control of forms, receipts, printers, slip printers, faxes etc. Multiple price groups and quantity price levels allowing maximum flexibility to different retail environments. Matrix pricing, kit pricing (both dynamic and static) with prices broken out or just single line on receipts. This software is our forth in 30 years and in our use since 2003. Regular updates and revisions are available to keep it fresh and up to date with changes in the ever changing retail industry. This is a very robust software and does far more than given here. #### Cons Back office reporting is probably the weekest area. However, custom reports are available and creatable. If you are looking into any software you should have a list of what you need to know daily, weekly and monthly and have it demonstrated to you. Another area is handling price protection from manufacturers. It is not easy to drop cost on items that receive price protection. It can be done but is time consuming. --- ### Windward System Five - Overall rating: 5/5 - Reviewer: Julie M. - Verified reviewer: Yes - Industry: Wholesale - Company size: 11-50 employees - Product usage: Used daily for more than 2 years - Reviewed: February 2021 - Review source details: This reviewer was invited by the software vendor to submit an honest review and offered a nominal incentive as a thank you. 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. #### Ratings breakdown - Ease of use: 5/5 - Value for money: 5/5 - Customer support: 4/5 - Functionality: 4/5 #### 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 #### Reasons for choosing Windward System Five The Windward system was able to give us what we needed to grow our company #### Reasons for switching to Windward System Five The old Sage Accpac did not have all the features we were needing especially the inventory module. Our company was growing and we needed a more sophisticated product. --- ### Windward System Five - I would recommend this program - Overall rating: 5/5 - Reviewer: Lynea B. - Verified reviewer: Yes - Industry: Wholesale - Company size: 2-10 employees - Product usage: Used daily for more than 2 years - Reviewed: July 2022 - Review source details: This reviewer was invited by us to submit an honest review and offered a nominal incentive as a thank you. Windward System Five is an easy to use program that allows people who have little experience to use it. #### Ratings breakdown - Ease of use: 5/5 - Customer support: 5/5 - Functionality: 5/5 #### 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. #### Reasons for choosing Windward System Five I started with Speedy POS as it was a similar product but less expensive so it made it more affordable for me. #### Reasons for switching to Windward System Five Inventory Control on Simply Accounting is terrible. --- ### excellent software for our industry - Overall rating: 5/5 - Reviewer: Stevenson B. - Verified reviewer: Yes - Industry: Retail - Company size: 2-10 employees - Product usage: Used daily for more than 2 years - Reviewed: June 2022 - Review source details: This reviewer was invited by us to submit an honest review and offered a nominal incentive as a thank you. #### Ratings breakdown - Ease of use: 5/5 - Value for money: 5/5 - Customer support: 5/5 - Functionality: 5/5 #### Pros sales reporting and inventory management. The accounting and payroll modules are great that they integrate with all other modules. #### Cons sometimes difficult to change and save settings on inventory reports. The payroll reports (designing) are difficult to understand #### Reasons for choosing Windward System Five recommendations, quality and ease of set up. #### Reasons for switching to Windward System Five Y2K and their pricing was out of line at the time --- ### Windward Review - Overall rating: 4/5 - Reviewer: Hyacinte S. - Verified reviewer: Yes - Industry: Restaurants - Company size: 2-10 employees - Product usage: Used daily for more than 2 years - Reviewed: June 2022 - Review source details: This reviewer was invited by us to submit an honest review and offered a nominal incentive as a thank you. When the system is working like we want it to it is a wonderful product. The customer support could be better with assistance. A lot of times when there are issues it is not easy to find the help in your help section. #### Ratings breakdown - Ease of use: 3/5 - Value for money: 2/5 - Customer support: 3/5 - Functionality: 4/5 #### Pros Ease of finding product, sales, general bookkeeping #### Cons When we integrated with online sales we found it very frustrating because it was not as easy as we were made to think it was. --- ### An Amazing Experience with Windward System Five - Overall rating: 5/5 - Reviewer: Jason S. - Product usage: Used unspecified for unspecified - Reviewed: May 2015 - Review source details: This review was submitted organically. No incentive was offered Since we have moved onto Windward System Five the improvement to our business have been and still remain extraordinary. System Five has given me the ability to work in an environment with real time information. With complete integration my business can process sales, my office team can work on accounting and financial transactions, inventory can be taken, purchase orders can be processed and more, all while maintaining flawless real-time information so that I can make decisions for my business quickly. In addition, we are able to process sales faster with integrated credit card processing, give a more profession look to our business with custom made integrated gift cards, we can print clean shelf labels right from the inventory record giving a profession look and assuring accurate pricing, barcode inventory items that do not have them, add multiple barcodes to items and a whole lot more.Support for this product is nothing short of impeccable! Windward offers 24/7 technical support from friendly, well trained technicians that work endlessly to keep your company up and running smoothly. The overall performance of this product in astonishing. 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. The customer service and support are friendly, understanding, concerned about your business needs and willing to do whatever it takes to help you run your company and accommodate your business needs. Speaking from one entrepreneur to you others out there, this is a product made for us! It is a fast, efficient, well build program that gives us the ability to run our businesses the way we want, collect information quickly with its wide array of reporting options so we can make better decisions, and free up our valuable time so we can get out there and do what we do best ' run our businesses! For those out there who would give this product anything less than a perfect review, I would like to challenge your business and management skill as the software is not the problem. This product gets five stars from me on all fronts! It's truly the integrity of my business and I could not imaging running my company without Windward System Five. For those of you considering I say go for it, it's the best investment you can make. #### Ratings breakdown - Ease of use: 5/5 - Customer support: 5/5 ## More reviews [Next reviews](https://www.softwareadvice.com/retail/windward-system-five-profile/reviews/?page=2) --- Windward System Five Reviews, Pros and Cons - 2026 Software Advice