--- description: Learn more about Windward System Five price, benefits, and disadvantages for businesses in Australia. Read reviews from verified users and discover similar tools that fit your business needs. image: https://gdm-localsites-assets-gfprod.imgix.net/images/capterra/og_logo-e5a8c001ed0bd1bb922639230fcea71a.png?auto=format%2Cenhance%2Ccompress title: Windward System Five Cost & Reviews - Capterra Australia 2026 --- Breadcrumb: [Home](/) > [Retail Management Software](/directory/20053/retail-management-systems/software) > [Windward System Five](/software/43189/windward-system-five) # Windward System Five Canonical: https://www.capterra.com.au/software/43189/windward-system-five Page: 1 / 9\ Next: [Next page](https://www.capterra.com.au/software/43189/windward-system-five?page=2) > All‑in‑one POS, inventory, CRM \& accounting—plus KPI dashboards (Windward Intelligence) and WebSell e‑commerce integration. > > Verdict: Rated **3.8/5** by 189 users. Top-rated for **Likelihood to recommend**. ----- ## Overview ### Who Uses Windward System Five? Independent SMBs in retail, wholesale, and service businesses needing a customizable POS + inventory + accounting suite with reporting and e‑commerce integration. ## 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**: USD 155.00 - **Pricing model**: Per User (Free Trial) - **Pricing Details**: Pricing plans range from $131 to $150\* 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), Linux (On-Premise) - **Supported Languages**: English - **Available Countries**: Australia, Canada, United States ## Features - Age Verification - Asset Tracking - Availability Management - Barcode/Ticket Scanning - Billing & Invoicing - CRM - Contract/License Management - Customer Management - Discount Management - Email Marketing - Employee Management - Gift Card Management - Inventory Management - Loyalty Program - Maintenance Management - Order Management - Ordering Automation - Payment Processing - Pricing Management - Purchase Order Management - Quotes/Estimates - Reporting/Analytics - Reservations Management - Retail Inventory Management - Returns Management - Returns Tracking - Sales Reports - Touch Screen - eCommerce Management ## Integrations (6 total) - Datacap - Global Payments Integrated - Polaris - 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.capterra.com.au/directory/20053/retail-management-systems/software) ## Related Categories - [Retail Management Software](https://www.capterra.com.au/directory/20053/retail-management-systems/software) - [Equipment Rental Software](https://www.capterra.com.au/directory/31717/equipment-rental/software) - [Retail POS Systems](https://www.capterra.com.au/directory/31656/retail-pos-system/software) - [Liquor Store POS Software](https://www.capterra.com.au/directory/32577/liquor-store-pos/software) ## Alternatives 1. [Epos Now](https://www.capterra.com.au/software/152638/epos-now) — 3.8/5 (713 reviews) 2. [Lightspeed Retail](https://www.capterra.com.au/software/120491/lightspeed-retail) — 4.0/5 (975 reviews) 3. [Shopify](https://www.capterra.com.au/software/83891/shopify) — 4.5/5 (6667 reviews) 4. [RetailEdge](https://www.capterra.com.au/software/76636/retailedge) — 4.8/5 (186 reviews) 5. [PayPal](https://www.capterra.com.au/software/179251/paypal) — 4.6/5 (26301 reviews) ## Reviews ### "My goodness do not buy this software." — 1.0/5 > **Greg** | *18 June 2025* | Retail | Recommendation rating: 0.0/10 > > **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. > > 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\! ----- ### "WindWard System 5 for Business" — 5.0/5 > **Shauna** | *13 November 2024* | Retail | Recommendation rating: 9.0/10 > > **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. > > 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. ----- ### "Slightly outdated, but intuitive and powerful" — 4.0/5 > **Mason** | *1 August 2025* | Consumer Goods | Recommendation rating: 6.0/10 > > **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. > > 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. ----- ### "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. ----- ### "FIX MOST ANY THING..FOR A COST" — 3.0/5 > **Jeff** | *30 April 2024* | Automotive | Recommendation rating: 3.0/10 > > **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. ----- Page: 1 / 9\ Next: [Next page](https://www.capterra.com.au/software/43189/windward-system-five?page=2) ## Links - [View on Capterra](https://www.capterra.com.au/software/43189/windward-system-five) ## This page is available in the following languages | Locale | URL | | de | | | de-AT | | | de-CH | | | en | | | en-AE | | | en-AU | | | en-CA | | | en-GB | | | en-IE | | | en-IL | | | en-IN | | | en-NZ | | | en-SG | | | en-ZA | | | es | | | es-AR | | | es-CL | | | es-CO | | | es-CR | | | es-DO | | | es-EC | | | es-MX | | | es-PA | | | es-PE | | | fr | | | fr-BE | | | fr-CA | | | fr-LU | | | it | | | pt | | | pt-PT | | ----- ## Structured Data