--- 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 for retail, wholesale \& service businesses. Real-time KPI dashboards. Expert support. > > Verdict: Rated **3.8/5** by 189 users. Top-rated for **Likelihood to recommend**. ----- ## Overview ### Who Uses Windward System Five? Independent retailers, wholesalers, and service businesses replacing disconnected apps with one configurable platform for POS, inventory, CRM, accounting, and real-time reporting. ## 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 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 - Accounting Integration - Accounts Payable - Accounts Receivable - Age Verification - Asset Tracking - Availability Management - Bank Reconciliation - Barcode/Ticket Scanning - Barcoding/RFID - Billing & Invoicing - Budgeting/Forecasting - CRM - Contract/License Management - Cost Tracking - Customer Accounts - Customer Management - Discount Management - Electronic Signature - Email Marketing - Employee Management - Expense Tracking - Financial Management - Financial Reporting - Fixed Asset Management - General Ledger - Gift Card Management - Inventory Management - Loyalty Program - Maintenance Management - Multi-Currency - Order Management - Ordering Automation - Payment Processing - Pricing Management - Purchase Order Management - Quotes/Estimates - Reorder Management - Reporting/Analytics - Reservations Management - Retail Inventory Management - Returns Management - Returns Tracking - Sales Reports - Supplier Management - Tax Management - Touch Screen - eCommerce 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.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) - [POS Systems](https://www.capterra.com.au/directory/20052/point-of-sale/software) - [Inventory Control Software](https://www.capterra.com.au/directory/30106/inventory-control/software) ## Alternatives 1. [Epos Now](https://www.capterra.com.au/software/152638/epos-now) — 3.8/5 (719 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 (6690 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 (26417 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\! ----- ### "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. ----- ### "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. ----- ### "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 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. ----- 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