--- description: Review of Windward System Five Software: system overview, features, price and cost information. Get free demos and compare to similar programs. image: https://gdm-localsites-assets-gfprod.imgix.net/images/software_advice/og_logo-55146305bbe7b450bea05c18e9be9c9a.png title: Windward System Five | Reviews, Pricing & Demos - SoftwareAdvice GB --- Breadcrumb: [Home](/) > [Retail Management Software](/directory/2025/retail-management/software) > [Windward System Five](/software/161668/windward-system-five) # Windward System Five Canonical: https://www.softwareadvice.co.uk/software/161668/windward-system-five Page: 1 / 9\ Next: [Next page](https://www.softwareadvice.co.uk/software/161668/windward-system-five?page=2) > 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 assemblies 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. > > Verdict: Rated **3.8/5** by 189 users. Top-rated for **Likelihood to recommend**. ----- ## Quick Stats & Ratings | Metric | Rating | Detail | | **Overall** | **3.8/5** | 189 Reviews | | Ease of Use | 3.7/5 | Based on overall reviews | | Customer Support | 3.7/5 | Based on overall reviews | | Value for Money | 3.6/5 | Based on overall reviews | | Features | 3.8/5 | Based on overall reviews | | Recommendation percentage | 70% | (7/10 Likelihood to recommend) | ## About the vendor - **Company**: Windward Software - **Location**: Penticton, Canada - **Founded**: 1984 ## Commercial Context - **Starting Price**: US$135.00 - **Pricing model**: Per User - **Pricing Details**: Pricing plans start at $135\* per user per month, plus a one-time implementation fee. \*based on user count. Note: Windward Software typically bills yearly, monthly rates are for comparative purposes. Talk to your rep for options. - **Target Audience**: Self Employed, 2–10, 11–50, 51–200 - **Deployment & Platforms**: Cloud, SaaS, Web-based, Windows (Desktop), Windows (On-Premise) - **Supported Languages**: English - **Available Countries**: Australia, Canada, United States ## Features - API - Access Controls/Permissions - Accounting Integration - Accounts Payable - Accounts Receivable - Activity Dashboard - Age Verification - Alerts/Notifications - Asset Lifecycle Management - Asset Tracking - Availability Indicator - Availability Management - Bank Reconciliation - Barcode Recognition - Barcode/Ticket Scanning - Barcoding/RFID - Billing & Invoicing - Budgeting/Forecasting - CRM - Calendar Management ## Integrations (8 total) - Datacap - Global Payments Integrated - Microsoft Power BI - Polaris - Shopify - WebSell - WooCommerce - Worldpay for Enterprise ## Support Options - Email/Help Desk - FAQs/Forum - Knowledge Base - Phone Support - 24/7 (Live rep) ## Category - [Retail Management Software](https://www.softwareadvice.co.uk/directory/2025/retail-management/software) ## Related Categories - [Retail Management Software](https://www.softwareadvice.co.uk/directory/2025/retail-management/software) - [Retail Accounting Software](https://www.softwareadvice.co.uk/directory/31/accounting-software/software) - [Liquor Store POS Software](https://www.softwareadvice.co.uk/directory/84/liquor-store-software/software) - [Sporting Goods POS Software](https://www.softwareadvice.co.uk/directory/109/sporting-goods-store-software/software) - [Furniture Store Software](https://www.softwareadvice.co.uk/directory/37/furniture-store-retail-software/software) ## Alternatives 1. [Epos Now](https://www.softwareadvice.co.uk/software/21000/epos-now) — 3.8/5 (719 reviews) 2. [Clover](https://www.softwareadvice.co.uk/software/61761/clover) — 3.8/5 (570 reviews) 3. [Shopify](https://www.softwareadvice.co.uk/software/390630/shopify) — 4.5/5 (6690 reviews) 4. [RetailEdge](https://www.softwareadvice.co.uk/software/1162/retailedge) — 4.8/5 (186 reviews) 5. [PayPal](https://www.softwareadvice.co.uk/software/104664/paypal) — 4.6/5 (26419 reviews) ## Reviews ### "Windward review" — 5.0/5 > **April** | *21 June 2022* | Consumer Services | Recommendation rating: 10.0/10 > > **Pros**: Unlimited features . Can do so much with a split business that we run. > > **Cons**: Would like to have more form creation options > > Well built system that covers a lot of different types of business. ----- ### "We couldn't live with our our System 5" — 5.0/5 > **Kathi** | *6 June 2024* | Retail | Recommendation rating: 9.0/10 > > **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. > > We couldn't do without them and their service is fantastic. ----- ### "Windward System 5 has made running our medium sized dealership much easier" — 5.0/5 > **Trish** | *25 October 2017* | Retail | Recommendation rating: 10.0/10 > > **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 > > Time and inventory management equals money savings ----- ### "Great system management" — 5.0/5 > **Nava** | *6 July 2022* | Building Materials | Recommendation rating: 8.0/10 > > **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. > > 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. ----- ### "Windward Review" — 4.0/5 > **Derek** | *20 June 2022* | Retail | Recommendation rating: 7.0/10 > > **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. > > Mostly positive when it comes to day to day interaction. Any negatives are more nit-picking issues. ----- Page: 1 / 9\ Next: [Next page](https://www.softwareadvice.co.uk/software/161668/windward-system-five?page=2) ## Links - [View on SoftwareAdvice](https://www.softwareadvice.co.uk/software/161668/windward-system-five) ## This page is available in the following languages | Locale | URL | | en | | | en-AU | | | en-GB | | | en-IE | | | en-NZ | | ----- ## Structured Data