# Windward System Five Software Reviews, Demo & Pricing - 2026 > Review of Windward System Five Software: system overview, features, price and cost information. Get free demos and compare to similar programs. Source: https://www.softwareadvice.com/retail/windward-system-five-profile --- [Home](https://www.softwareadvice.com/) / [Retail Management Systems Software](https://www.softwareadvice.com/retail/retail-management-comparison/) / Windward System Five 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 [Reviews](https://www.softwareadvice.com/retail/windward-system-five-profile/reviews/)[Alternatives](https://www.softwareadvice.com/retail/windward-system-five-profile/alternatives/) # Windward System Five 2026: Benefits, Features & Pricing Wondering if Windward System Five is right for your organization? Our Retail Management Systems Software selection experts can help you in 15 minutes or less. On this page - Overview - User Interface - Popular Alternatives - Pros and Cons - Pricing and Plans - Features - Integrations - User Reviews - Popular Comparisons ## Overview Windward System Five 3.8 [(189)](https://www.softwareadvice.com/retail/windward-system-five-profile/reviews/) Pricing Starting at $135.00 per month ### About Windward System Five Windward System Five is a complete business management platform built for independent retailers, wholesalers, service businesses, equipment rental operations, and specialty stores. It brings point of sale, inventory control, purchasing, CRM, and accounting into one connected system — replacing the patchwork of disconnected tools with a single source of truth. Most independents are running on a stack of disconnected apps: a basic POS, a separate accounting package, spreadsheets for inventory, another system for customer data. The result is duplicate entry, reconciliation headaches, and reporting that's always weeks behind reality. Windward System Five consolidates these into one integrated platform where the front counter, back office, and books share the same data in real time. Point of Sale Ring sales quickly with a configurable POS built for real retail. Accept multiple payment types, process returns and exchanges, and manage layaways, gift cards, loyalty programs, special orders, and quotes. Multi-location stores get real-time inventory, customer history, and pricing across every store. Built-in support for serialized items, matrix products (size/color/style), kits, and assemb... lies handles complex catalogs without workarounds. Inventory Control Track inventory by SKU, serial, lot, or matrix across single or multiple locations. Manage purchase orders, receiving, supplier price lists, transfers, reorder points, and physical counts. Inventory updates in real time as sales, returns, and adjustments happen — and connects directly to accounting, eliminating the reconciliation work that comes with siloed systems. Equipment Rental For rental and mixed rental/retail operations, System Five manages rental contracts, reservations, returns, deposits, late fees, and damage charges alongside parts and service. Track every unit by serial number, location, and rental status, with support for short- and long-term contracts and recurring billing. Liquor & Specialty Retail Liquor, wine, and beverage retailers get purpose-built tools: case breaks, mix-and-match cases, multi-pack pricing, bottle deposits, and inventory by vintage or supplier — single store or multi-location. Accounting Run general ledger, accounts receivable, accounts payable, and bank reconciliation directly from operational activity. Every transaction posts to the books automatically — eliminating month-end cleanup and giving owners real-time visibility into profitability and cash position. CRM & Customer Management Build repeat business with complete customer history at the counter — past purchases, preferences, special orders, account balances, and contact details. Drive loyalty programs and targeted promotions from the same data running your sales and accounting. Windward Intelligence The built-in KPI dashboard puts the metrics that matter in front of owners and managers in real time: sales by store, staff, item, and customer; margins by category; inventory turn; dead stock; rental utilization; and customer trends. Stop waiting for end-of-month reports to find out what's happening — act on data the same day. Configurable to Fit Your Business Independent businesses run differently from chains, and from each other. Windward System Five is highly configurable — adjust the chart of accounts, customize POS screens, set pricing rules, define user permissions, and tailor reporting to match how your business actually operates. Personalized Onboarding, Training, and Support Every customer gets hands-on onboarding, training, and ongoing live support from a team that knows the software inside out. No ticket queues, no offshore call centers — real people who help you get the most out of the platform. Independent retailers, wholesalers, service businesses, equipment rental operations, and specialty stores choose Windward System Five to run their operations from one trusted platform. Discover what an integrated business management system can do for yours. Wondering if Windward System Five is right for your organization? Our Retail Management Systems Software selection experts can help you in 15 minutes or less. ## Windward System Five User Interface ## Popular Windward System Five Alternatives Main Product Windward System Five 3.8 [(189)](https://www.softwareadvice.com/retail/windward-system-five-profile/reviews/) Ratings Breakdown - 3.66Ease of use - 3.58Value for money - 3.75Customer support - 3.80Functionality Pricing Starting at $135.00 per month Get Price Alternative Product [Epos Now](https://www.softwareadvice.com/retail/epos-now-profile/) 3.8 [(721)](https://www.softwareadvice.com/retail/epos-now-profile/reviews/) Ratings Breakdown - 3.84Ease of use - 3.61Value for money - 3.62Customer support - 3.76Functionality Pricing Starting at $349.00 one time Get Price Alternative Product [Clover](https://www.softwareadvice.com/retail/clover-profile/) 3.8 [(575)](https://www.softwareadvice.com/retail/clover-profile/reviews/) Ratings Breakdown - 4.01Ease of use - 3.42Value for money - 3.24Customer support - 3.78Functionality Pricing Available upon request Get Price Alternative Product [Shopify](https://www.softwareadvice.com/retail/shopify-profile/) 4.5 [(6694)](https://www.softwareadvice.com/retail/shopify-profile/reviews/) Ratings Breakdown - 4.47Ease of use - 4.29Value for money - 4.35Customer support - 4.43Functionality Pricing Starting at $29.00 per month Get Price Alternative Product [RetailEdge](https://www.softwareadvice.com/retail/retailedge-profile/) 4.8 [(187)](https://www.softwareadvice.com/retail/retailedge-profile/reviews/) Ratings Breakdown - 4.66Ease of use - 4.82Value for money - 4.80Customer support - 4.59Functionality Pricing Starting at $495.00 one time Get Price Alternative Product [PayPal](https://www.softwareadvice.com/retail/paypal-profile/) 4.6 [(26451)](https://www.softwareadvice.com/retail/paypal-profile/reviews/) Ratings Breakdown - 4.64Ease of use - 4.52Value for money - 4.25Customer support - 4.56Functionality Pricing Available upon request Get Price ## Windward System Five Pros and Cons We analyzed 189 verified reviews for Windward System Five to find out what actual users really think. Select to learn more Detailed Inventory Tracking Tools Windward System Five offers robust inventory management with real-time tracking, detailed reporting, and easy import/export options. Users appreciate its ability to handle large inventories, streamline reordering, and integrate with accounting, making daily operations and stock control more efficient. Slow And Inconsistent Support Help Many users report that customer support is difficult to reach, slow to resolve issues, and often provides only temporary fixes. Complaints include long wait times, lack of knowledgeable staff, expensive support fees, and frustration with overseas call centers. ## Windward System Five Pricing and Plans Starting price: $135.00 per month Free Trial Free Version System Five on Cloud with Partner Processing $135.00 per user, per month Plan includes: - 24/7 Live Customer Support - 2-Factor Authentication - Secure Cloud Backup - Updates Included - Windward Intelligence - Partner Credit Card Processing System Five on Cloud Standard $149.00 per user, per month Plan includes: - 24/7 Live Customer Support - 2-Factor Authentication - Secure Cloud Backup - Updates Included - Windward Intelligence System Five on Cloud Monthly $179.00 per user, per month Plan includes: - 24/7 Live Customer Support - 2-Factor Authentication - Secure Cloud Backup - Updates Included - Windward Intelligence Confused about pricing? We've got you covered. Get a personalized pricing breakdown tailored to your specific needs—no guesswork, no generic estimates. ## Windward System Five Features - Popular features found in Retail Management Systems Accounting Integration CRM eCommerce Management Employee Management Loyalty Program Merchandise Management Multi-Location Order Management Purchase Order Management Reporting/Analytics Retail Inventory Management Returns Management - More features of Windward System Five Access Controls/Permissions Accounting Accounts Payable Accounts Receivable Activity Dashboard Age Verification Alerts/Notifications API Asset Lifecycle Management Asset Tracking Availability Indicator Availability Management Bank Reconciliation Barcode Recognition Barcode/Ticket Scanning Barcoding/RFID Billing & Invoicing Budgeting/Forecasting Calendar Management Cash Flow Management Cash Management Chart of Accounts Check-in/Check-out Commission Management Contract/License Management Cost Tracking Credit Card Processing Currency Conversion Customer Accounts Customer Database Customer History Customer Management Customizable Fields Customizable Reports Data Import/Export Data Synchronization Discount Management Document Management Document Storage Electronic Signature Email Marketing Expense Tracking Financial Management Financial Reporting Fixed Asset Management Fleet Management Forecasting For Liquor Stores For Retail General Ledger Gift Card Management Income & Balance Sheet Inspection Management Inventory Management Inventory Optimization Inventory Replenishment Inventory Tracking Invoice Management Item Management Layaway Management Maintenance Management Maintenance Scheduling Multi-Channel Management Multi-Currency Ordering Automation Order Processing Order Tracking Payment Processing Point of Sale (POS) Price/Margin Management Pricing Management Product Catalog Product Identification Project Management Promotions Management Purchasing & Receiving Quotes/Estimates Real-Time Analytics Real-Time Data Real-Time Monitoring Real-Time Reporting Real-Time Updates Receipt Management Reorder Management Reporting & Statistics Reservations Management Retail Management Retail POS Returns Tracking Sales Order Management Sales Reports Sales Tax Management Sales Trend Analysis Scheduling Search/Filter Serial Number Tracking Shipping Management SKU/UPC Codes Stock Management Supplier Management Tax Management Third-Party Integrations Touch Screen Transaction History Utilization Reporting Warehouse Management Work Order Management ## Windward System Five Integrations Worldpay for Enterprise Integration rated undefined from -1 review Datacap Integration rated undefined from -1 review WooCommerce Integration rated undefined from -1 review Global Payments Integrated Integration rated undefined from -1 review WebSell Integration rated undefined from -1 review Microsoft Power BI Integration rated undefined from -1 review See all 7 integrations ## Windward System Five User Reviews Overall Rating 3.8 Ratings Breakdown 5 38% 4 34% 3 11% 2 8% 1 10% Secondary Ratings Ease of Use 3.7 Value for money 3.6 Customer support 3.7 Functionality 3.8 AT April T. Verified reviewer Consumer Services 11-50 employees Used daily for more than 2 years Reviewed June 2022 Windward review 5 Previously 4 Well built system that covers a lot of different types of business. Ratings Breakdown 5 Ease of use Previously 4 4 Value for money 5 Customer support 5 Functionality Previously 4 Pros: Unlimited features . Can do so much with a split business that we run. Cons: Would like to have more form creation options Read More NC Nava C. Verified reviewer Building Materials 2-10 employees Used daily for more than 2 years Review source Reviewed July 2022 Great system management 5 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 4 Ease of use 4 Value for money 5 Customer support 5 Functionality 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. Read More TH Trish H. Retail 11-50 employees Used daily for more than 2 years Review source Reviewed October 2017 Windward System 5 has made running our medium sized dealership much easier 5 Time and inventory management equals money savings Ratings Breakdown 4 Ease of use Previously 5 4 Value for money Previously 5 5 Customer support 5 Functionality 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 Read More KM Kathi M. Verified reviewer Retail 2-10 employees Used daily for more than 2 years Reviewed June 2024 We couldn't live with our our System 5 5 We couldn't do without them and their service is fantastic. Ratings Breakdown 4 Ease of use 4 Value for money 5 Customer support 4 Functionality 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 Read More DS Derek S. Verified reviewer Retail 11-50 employees Used daily for more than 2 years Reviewed June 2022 Windward Review 4 Mostly positive when it comes to day to day interaction. Any negatives are more nit-picking issues. Ratings Breakdown 4 Ease of use 4 Value for money 5 Customer support 2 Functionality 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 Read More JG Jeff G. Verified reviewer Automotive 11-50 employees Used daily for more than 2 years Review source Reviewed April 2024 FIX MOST ANY THING..FOR A COST 3 Ratings Breakdown 3 Ease of use 3 Value for money 1 Customer support 3 Functionality 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 Read More BN Bob N. Verified reviewer Furniture 2-10 employees Used daily for less than 2 years Reviewed June 2022 continuing forward 2 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 1 Ease of use 2 Value for money 4 Customer support 2 Functionality 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. Read More RF Rossie F. Verified reviewer Retail 2-10 employees Used daily for more than 2 years Reviewed June 2022 Windward Software is an amazing program to help you run your business in every aspect. 5 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 5 Ease of use 5 Value for money 5 Customer support 5 Functionality 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. Read More TM Tami M. Verified reviewer Recreational Facilities and Services 11-50 employees Used daily for less than 2 years Review source Reviewed June 2022 Tami McQuown 4 Its been a great experience! Ratings Breakdown 3 Ease of use 4 Value for money 5 Customer support 3 Functionality 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 Read More MB Mason B. Verified reviewer Consumer Goods 2-10 employees Used monthly for less than 2 years Review source Reviewed August 2025 Slightly outdated, but intuitive and powerful 4 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 4 Ease of use 4 Functionality 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. Read More Showing 1 - 10 of 189 Reviews [See All Reviews](https://www.softwareadvice.com/retail/windward-system-five-profile/reviews/) ## Windward System Five Popular Comparisons [Epos Now vs Windward System Five](https://www.softwareadvice.com/retail/epos-now-profile/vs/windward-system-five/)[Clover vs Windward System Five](https://www.softwareadvice.com/retail/clover-profile/vs/windward-system-five/)[Shopify vs Windward System Five](https://www.softwareadvice.com/retail/shopify-profile/vs/windward-system-five/)[RetailEdge vs Windward System Five](https://www.softwareadvice.com/retail/retailedge-profile/vs/windward-system-five/)[PayPal vs Windward System Five](https://www.softwareadvice.com/retail/paypal-profile/vs/windward-system-five/)[Like Sew vs Windward System Five](https://www.softwareadvice.com/compare/161668-windward-system-five/vs/449886-Like-Sew/)[Rain POS vs Windward System Five](https://www.softwareadvice.com/retail/rainpos-profile/vs/windward-system-five/)[Meevo vs Windward System Five](https://www.softwareadvice.com/retail/meevo-profile/vs/windward-system-five/) [Compare All Alternatives](https://www.softwareadvice.com/retail/windward-system-five-profile/alternatives/) ## Other Top Recommended Retail Management Systems Software [Clover](https://www.softwareadvice.com/retail/clover-profile/) **3.8** (575) Recently recommended **91** times [Toast POS](https://www.softwareadvice.com/retail/toast-pos-profile/) **4.2** (552) Recently recommended **69** times [Rain POS](https://www.softwareadvice.com/retail/rainpos-profile/) **4.1** (134) Recently recommended **49** times [Epos Now](https://www.softwareadvice.com/retail/epos-now-profile/) **3.8** (721) Recently recommended **52** times Stuck Between Options? 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