# Windward System Five Software Pricing, Alternatives & More 2026 | Capterra > With the help of Capterra, learn about Windward System Five Software - reviews, pricing plans, popular comparisons to other Retail Management Systems products and more. Source: https://www.capterra.com/p/43189/Windward-System-Five --- # Windward System Five Software Review 2026: Features, Integrations, Pros & Cons Last updated on March 13, 2026 Provider data verified by our Software Research team, and reviews moderated by our Reviews Verification team. Independent research methodology Capterra’s researchers use a mix of verified reviews, independent research and objective methodologies to bring you selection and ranking information you can trust. While we may earn a referral fee when you visit a provider through our links or speak to an advisor, this has no influence on our research or methodology. 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[Learn more](https://www.capterra.com/resources/how-we-ensure-transparency/) [Description](#description)[Use cases](#use-cases)[Alternatives](#alternatives)[Pros and Cons](#pros-cons)[Features](#features)[Pricing](#pricing)[Integrations](#integrations)[Support](#support)[Reviews](#reviews) Windward System Five ## What is Windward System Five? Windward System Five is an all‑in‑one business management platform that brings point of sale, inventory control, CRM, and accounting into one system. Run purchasing and receiving, manage work/special orders, fulfill and invoice customers, and track accounts receivable—so your team can operate from one source of truth. Built‑in reporting is extended with Windward Intelligence, a KPI dashboard that helps you monitor sales, margins, customers, and more. For omnichannel selling, connect System Five to WebSell to sync products and customers and handle web orders using the same workflows as in‑store. Highly configurable to fit complex operations, backed by personalized support and training. ## What is Windward System Five used for? [Retail POS System](https://www.capterra.com/retail-pos-system-software/)[Retail Management Systems](https://www.capterra.com/retail-management-systems-software/)[Equipment Rental](https://www.capterra.com/equipment-rental-software/) Top alternative Featured Overall rating Based on 189 user reviews Reviews sentiment Positive 71% Neutral 11% Negative 18% Pros & cons Comprehensive inventory tracking tools Inconsistent support experiences Frequent technical problems Starting price $155 Per User, Per Month Free trial available Capterra Shortlist charts the highest-rated and most popular products... Our "Best of" badge program showcases products with the highest ratings... Our "Best of" badge program showcases products with the highest ratings... Do you work for Windward System Five?[Manage this product listing](https://digitalmarkets.gartner.com/get-listed/claim-bx?url=http://www.windwardsoftware.com&name=Windward System Five) ## Compare with a popular alternative Capterra selects software alternatives based on relevant features, verified user reviews and user interactions. Placement may be influenced by client status. ### Windward System Five 3.8 (189) VS. [3.8 (714)](https://www.capterra.com/p/152638/Epos-Now/reviews/) Starting Price $155 Per User, Per Month Starting Price $349 Flat Rate, One Time Free Trial Free Version Pricing Options Free Trial Free Version Ease Of Use 3.7 (189) Ease Of Use 3.8 (714) Value For Money 3.6 (153) Value For Money 3.6 (667) Customer Service 3.7 (187) Customer Service 3.6 (689) ## Windward System Five alternatives [4.8 (186)](https://www.capterra.com/p/76636/RetailEdge/reviews/) Starting price $495.00 Per User, Per Month Pricing Options Free Trial Free Version User Rating 98% of reviewers rated it above 4 stars [4.4 (276)](https://www.capterra.com/p/172058/Meevo-2/reviews/) Starting price Contact vendor for pricing Pricing Options Free Trial Free Version User Rating 84% of reviewers rated it above 4 stars Highest Rated [4.9 (163)](https://www.capterra.com/p/120411/Datascan-Pharmacy-Software/reviews/) Starting price $2500.00 Per User, Per Month Pricing Options Free Trial Free Version User Rating 99% of reviewers rated it above 4 stars [4.8 (1,134)](https://www.capterra.com/p/138689/Booqable/reviews/) Starting price $29.00 Per User, Per Month Pricing Options Free Trial Free Version User Rating 98% of reviewers rated it above 4 stars [View all alternatives](https://www.capterra.com/p/43189/Windward-System-Five/alternatives/) ## Pros and Cons Comprehensive inventory tracking tools 82% positive reviews out of 45 Most reviewers find inventory management streamlines tracking, reporting, and reordering, saving time and improving accuracy. 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." Inconsistent support experiences 46% negative reviews out of 78 Some reviewers describe customer support as slow, unhelpful, and difficult to reach, leading to unresolved problems. Frequent technical problems 89% negative reviews out of 36 Most users report bugs and issues disrupt daily operations, causing frustration and ongoing workflow interruptions. 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." ## Features Features with the highest number of reviews are displayed first. Those that have no reviews appear next, sorted alphabetically. Point of Sale (POS) 3.8 (25) 64.00% of 25 reviewers that rated this feature as important or highly important Accept and process customer payments for products or services using hardware and software Sales Reports 4.2 (25) 52.00% of 25 reviewers that rated this feature as important or highly important Reports specific to sales analysis for trends and strategies Inventory Management 3.9 (23) 82.61% of 23 reviewers that rated this feature as important or highly important Track and manage inventory levels to maintain proper supply Cost Tracking 3.9 (19) 57.89% of 19 reviewers that rated this feature as important or highly important Process to track, record, and analyze expenses that occurred over the entire duration of a given project For Retail 3.4 (16) 68.75% of 16 reviewers that rated this feature as important or highly important For Retail Stores Order Management 3.7 (15) 53.33% of 15 reviewers that rated this feature as important or highly important Manage and track customer orders for goods, investments, or any other purchases Windward System Five 92 features Define levels of authorization for access to specific files or systems Integrate with a third-party accounting system Dashboard to view the status of ongoing processes, identify current incidents and track past activities A way for institutions and businesses to check the age of their customers/clients. Alerts or notifications of various types such as pop-up messages, sounds, banners, or badges Application programming interface that allows for integration with other systems/databases Manage assets throughout their lifecycle to optimize profit Monitor the usage of assets, such as equipment, tools, software, etc., throughout their lifecycle Indication whether a resource is available or protected from allocation Monitor and analyze the availability of resources to help plan and streamline the service delivery to clients The ability to identify a barcode on or within an image or packaging Scan barcodes to ensure accurate pricing and label tracking Identify and track items using barcode tags or RFID (radio-frequency identification) tags Create, manage, and send invoices or bills to customers Track and manage schedules and meetings via an integrated calendar Process of managing an organization's cash resources, including cash on hand, investments, and bank account balances Tracking, calculating, and paying commissions and earnings to employees Track, store, and access client contracts or licenses Process to track, record, and analyze expenses that occurred over the entire duration of a given project Accept and process credit card transactions Built-in customer relationship management (CRM) capabilities or integration with a third-party CRM system Record customer information, purchase history, and other notes A collection of customer information such as contact details, demographics, previous interactions, etc. Access previous interactions or concerns to maintain customer relationships Store and organize information about customers and previous interactions Alter the layout and content of reports Import and export data to and from software applications Synchronizing data between two or more devices/systems and automatically updating changes to maintain consistency Track products that are for sale at a reduced price or part of coupon promotions Store, manage, and track all electronic documents in a centralized location Store and organize documents in a centralized system Has a built-in eCommerce system or integrates with third-party systems to manage online sale of products Digitally sign online documents Create and send email blasts/campaigns Track employee schedules, availability, and performance across projects and tasks Software designed for use by liquor stores For Retail Stores Form predictions based on past and present data/trends Reward loyal customers with gift cards which they can redeem for special offers and loyalty bonus Track and manage inspections for worksites, vehicles, and/or equipment to remain compliant with industry standards Track and manage inventory levels to maintain proper supply Maintain and control the stock level of inventory Track stock count levels to manage product reordering Track and monitor inventory items, such as raw materials, unfinished goods, and ready-to-sell items Captures invoice data and maintains comprehensive records for auditing and reporting purposes Collect, organize, and track inventory/product data including item numbers, descriptions, etc. Offer prizes, discounts, and other incentives for customers to earn reward points on purchases and redeem them for future purchases Manage, maintain and track the performance of assets and equipment Schedule predetermined or ad hoc maintenance services and labor requests Provides intelligence to make the right inventory purchasing decisions. Manage inventory, communication, marketing, orders & more across warehouses, stores and online channels Manage and handle various international currencies Manage and support multiple locations Manage and track customer orders for goods, investments, or any other purchases Automate order processes to improve operational efficiency in fulfillment, shipping, and more Accept, record, and reconcile financial transactions Accept and process customer payments for products or services using hardware and software Track and manage the profit margin between the cost of a product and its selling price. Tool used to determine accurate pricing and product eligibility for borrowers Present a catalog of inventory that customers can view Ability to link barcodes or serial numbers with specific items for identification Design, communicate, and distribute incentives to perform a specific action Create, send, and track purchase orders and their statuses Generate quotes or estimates for customers Analyze and gain insights into data in real-time Receive data and information in real time Active monitoring of systems, applications, or networks Active reporting of data and metrics Receive system updates as soon as any changes are made Upload, track, and submit receipts in a central database Collection, analysis, and representation of numerical data and generation of reports to understand various patterns View and track pertinent metrics to find patterns and gain insights from data Manage the entire lifecycle of a reservation, from the initial booking to the actual service or event Tracking, organizing, and controlling retail inventory throughout the supply chain and sales process Manage sales in retail stores Track and facilitate returns of products sold See what items have been returned An order generated by a seller to a customer, containing details about products or services Reports specific to sales analysis for trends and strategies Calculation of consumption tax imposed on the sale of goods/services Analyze the current state of sales data to accurately understand trends and forecast future sales numbers. Plan availability and assign specific time slots for tasks and resources Search and filter data across systems to locate required information by entering keywords or certain criteria Manage and track orders being shipped to customers Manage the buying, selling, and holding of stocks Manage all supplier data and operations Set up connections to third-party platforms to improve business processes Interactivity between software and users by touching areas on the screen of display devices Record of all transactions such as purchases, deposits, withdrawals and transfers within a specific period Track the frequency of asset usage Manage and track operations and inventory within warehouses Creating, assign, and track jobs and/or tasks for work orders Get Advice We can help you find the software with the features you need. Features 3.8 (164) 3.8 Based on 164 reviews ## Pricing Value for money 3.6 (153) Free Trial [View pricing plan details](https://www.capterra.com/p/43189/Windward-System-Five/pricing/) 2-10 Users $155.00 Per User,Per Month It includes: - 24/7 Live Customer Support - 2-Factor Authentication - Add Ons – Advanced Inventory Control - Contractor Solution - Department Solution - Health Billing (ADP AADL) - Multi-Currency - Payroll - Secure Cloud Backup - Updates Included - Windward Intelligence - Windward SCAN App 11-20 Users $139.00 Per User,Per Month It includes: - 24/7 Live Customer Support - 2-Factor Authentication - Add Ons – Advanced Inventory Control - Contractor Solution - Department Solution - Health Billing (ADP AADL) - Multi-Currency - Payroll - Secure Cloud Backup - Updates Included - Windward Intelligence - Windward SCAN App 21+ Users $135.00 Per User,Per Month It includes: - 24/7 Live Customer Support - 2-Factor Authentication - Add Ons – Advanced Inventory Control - Contractor Solution - Department Solution - Health Billing (ADP AADL) - Multi-Currency - Payroll - Secure Cloud Backup - Updates Included - Windward Intelligence - Windward SCAN App Value for money 3.6 (153) 3.6 Based on 153 reviews ## Integrations [ WooCommerce](https://www.capterra.com/p/225601/WooCommerce/)[ Global Payments Integrated](https://www.capterra.com/p/121910/OpenEdge/)[ WebSell](https://www.capterra.com/p/200087/NitroSell/)[ Worldpay for Enterprise](https://www.capterra.com/p/165694/Virtual-Terminal/)[ Datacap](https://www.capterra.com/p/10001915/NETePay/)[ Polaris](https://www.capterra.com/p/218464/Polaris/) Connect with a Capterra advisor for a free 15-minute consultation Get a personalized software list aligned to your business needs with guidance from our expert advisors. Our team has helped 1 million+ businesses like yours find options that fit their needs. ## Support, customer service and training options Customer Service 3.7 (187) Support - Email/Help Desk - FAQs/Forum - Knowledge Base - Phone Support - 24/7 (Live rep) - Chat Training - In Person - Live Online - Webinars - Documentation - Videos Deployment - Web - Android - iPhone/iPad Typical users - Freelancers - Small businesses - Mid size businesses - Enterprises Customer Service 3.7 (187) 3.7 Based on 187 reviews ## User reviews Overall rating 3.8 Based on 189 reviews Filter by rating 5(69) 4(66) 3(20) 2(15) 1(19) Mentioned topic Sorted by most recent MB Mason B. Sales Associate Consumer Goods ### "Slightly outdated, but intuitive and powerful" 4.0 Overall Rating 4.0 4.0 Ease of Use 4.0 4.0 Features 4.0 4.0 Customer Service 0.0 0.0 Likelihood to Recommend 6/10 August 1, 2025 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. 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. Review source Incentivized review: software users are invited to submit an honest review and offered a nominal incentive for their time and effort. All incentivized reviews are subject to our verification process prior to publication. GH Greg H. Owner Retail ### "My goodness do not buy this software." 1.0 Overall Rating 1.0 1.0 Ease of Use 4.0 4.0 Features 5.0 5.0 Customer Service 1.0 1.0 Likelihood to Recommend 0/10 June 18, 2025 Please please please save yourself - DO NOT buy into this software. It looks so good from the outside but once you're working in it every day, nothing works the way it is supposed to. 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. Development is out of control - one developer in one area will fix something but that will break 4 other things in other areas. Developer 2 will fix what developer 1 broke, but it re-breaks the original problem. Rinse and repeat forever. From one of System 5's oldest customers - stay out of this swamp! Pros Extremely versatile and powerful. If you want to do something, System Five probably does it. The interface is good, we host on premises so performance is generally OK (after 20+ years our dataset is getting big and some reports are slow.) Cons Nothing works properly. Support is absolutely - top to bottom - terrible. Very expensive - literally 22.5 TIMES the cost of the software we tried to replace it with. Very difficult to move away from - their database structure is as well thought out as a dump truck full of spaghetti. Exporting our data is a nightmare. Review source Non-incentivized review: any software user can leave a review for any product listed on our site. All submitted reviews are subject to our verification process prior to publication. SH Shauna H. Accounts Payable Manager and Bookkeeping Assistant Retail ### "WindWard System 5 for Business" 5.0 Overall Rating 5.0 5.0 Ease of Use 3.0 3.0 Features 4.0 4.0 Customer Service 3.0 3.0 Likelihood to Recommend 9/10 November 13, 2024 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. 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. Review source Incentivized review: software users are invited to submit an honest review and offered a nominal incentive for their time and effort. All incentivized reviews are subject to our verification process prior to publication. KM Kathi M. CEO Retail ### "We couldn't live with our our System 5" 5.0 Overall Rating 5.0 5.0 Ease of Use 4.0 4.0 Features 4.0 4.0 Customer Service 5.0 5.0 Likelihood to Recommend 9/10 June 6, 2024 We couldn't do without them and their service is fantastic. 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. Switched from [QuickBooks Enterprise](https://www.capterra.com/p/174984/QuickBooks-Enterprise/) 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. 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. Review source Incentivized review: software users are invited to submit an honest review and offered a nominal incentive for their time and effort. All incentivized reviews are subject to our verification process prior to publication. Response from Vendor September 9, 2024 Thanks for your review! We're sure it will help a business owner make the right call by switching to Windward Software. JG Jeff G. PARTS MANAGER Automotive ### "FIX MOST ANY THING..FOR A COST" 3.0 Overall Rating 3.0 3.0 Ease of Use 3.0 3.0 Features 3.0 3.0 Customer Service 1.0 1.0 Likelihood to Recommend 3/10 April 30, 2024 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. Switched from [AutoShop](https://www.capterra.com/p/35810/AutoShop/) Was promised Winward could do every thing we needed. Review source Non-incentivized review: any software user can leave a review for any product listed on our site. All submitted reviews are subject to our verification process prior to publication. Response from Vendor May 17, 2024 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. TM Trina M. Owner Retail ### "System five review" 4.0 Overall Rating 4.0 4.0 Ease of Use 4.0 4.0 Features 4.0 4.0 Customer Service 5.0 5.0 Likelihood to Recommend 5/10 December 18, 2023 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 Incentivized review: software users are invited to submit an honest review and offered a nominal incentive for their time and effort. All incentivized reviews are subject to our verification process prior to publication. AU Anatoly U. owner Retail ### "Stay Away, poor Company and Poor program full of glitches" 2.0 Overall Rating 2.0 2.0 Ease of Use 1.0 1.0 Features 1.0 1.0 Customer Service 1.0 1.0 Likelihood to Recommend 0/10 September 2, 2023 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 Non-incentivized review: any software user can leave a review for any product listed on our site. All submitted reviews are subject to our verification process prior to publication. Response from Vendor 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. JR Joellyn R. Owner Furniture ### "Windward" 4.0 Overall Rating 4.0 4.0 Ease of Use 4.0 4.0 Features 4.0 4.0 Customer Service 5.0 5.0 Likelihood to Recommend 9/10 July 31, 2023 Pros Invoicing. It is easy with Windward for all invoicing. Cons Needing more specialized reporting---hard to create Review source Incentivized review: software users are invited to submit an honest review and offered a nominal incentive for their time and effort. All incentivized reviews are subject to our verification process prior to publication. LB Lauren B. Office Manager Retail ### "Windward Software exceeds our expectations" 5.0 Overall Rating 5.0 5.0 Ease of Use 5.0 5.0 Features 5.0 5.0 Customer Service 5.0 5.0 Likelihood to Recommend 10/10 December 6, 2022 Pros I love that it is typically smooth and easy to use. Cons I wish it integrated better with our ecommerce but I know that is coming! Review source Incentivized review: software users are invited to submit an honest review and offered a nominal incentive for their time and effort. All incentivized reviews are subject to our verification process prior to publication. Response from Vendor December 7, 2022 Thanks Lauren! This will certainly be helpful to those looking at Windward System Five to help them run their business. GC Giuseppe C. Disoccupato Farming ### "Ottimo windward system Five" 5.0 Overall Rating 5.0 5.0 Ease of Use 5.0 5.0 Features 5.0 5.0 Customer Service 5.0 5.0 Likelihood to Recommend 0/10 December 6, 2022 Ottima Pros Tutto e un bellissimo software lo consiglio Cons Niente è ottimo software per le persone Review source Incentivized review: software users are invited to submit an honest review and offered a nominal incentive for their time and effort. All incentivized reviews are subject to our verification process prior to publication. Response from Vendor December 14, 2022 Thanks for the product review! 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