--- description: Learn more about Windward System Five pricing, benefits, and disadvantages for your business in Canada. Read verified software reviews and find 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 Pricing, Reviews & Features - Capterra Canada 2026 --- Breadcrumb: [Home](/) > [Equipment Rental Software](/directory/31717/equipment-rental/software) > [Windward System Five](/software/43189/windward-system-five) # Windward System Five Canonical: https://www.capterra.ca/software/43189/windward-system-five Page: 1 / 9\ Next: [Next page](https://www.capterra.ca/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 Software | 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 - Access Controls/Permissions - Accounting Integration - Accounts Payable Software - Accounts Receivable Software - Age Verification - Asset Tracking Software - Availability Management - Bank Reconciliation - Barcode/Ticket Scanning - Barcoding/RFID - Billing & Invoicing - Budgeting/Forecasting - CRM Software - Contract/License Management - Cost Tracking - Customer Accounts - Customer Management - Discount Management - Electronic Signature - Email Marketing Software - Employee Management - Expense Tracking - Financial Management Software - Financial Reporting Software - Fixed Asset Management Software - General Ledger - Gift Card Management - Inventory Management Software - Loyalty Program - Maintenance Management Software - Multi-Currency - Order Management Software - Ordering Automation - Payment Processing Software - Pricing Management - Project Management Software - Purchase Order Management - Quotes/Estimates - Reorder Management - Reporting & Statistics - Reporting/Analytics - Reservations Management - Retail Inventory Management Software - Returns Management - Returns Tracking - Sales Reports - Supplier Management - Tax Management Software - 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 Software - Phone Support - 24/7 (Live rep) ## Category - [Equipment Rental Software](https://www.capterra.ca/directory/31717/equipment-rental/software) ## Related Categories - [Retail Management Systems Software](https://www.capterra.ca/directory/20053/retail-management-systems/software) - [Equipment Rental Software](https://www.capterra.ca/directory/31717/equipment-rental/software) - [Retail POS System Software](https://www.capterra.ca/directory/31656/retail-pos-system/software) - [Point of Sale Software](https://www.capterra.ca/directory/20052/point-of-sale/software) - [Inventory Control Software](https://www.capterra.ca/directory/30106/inventory-control/software) ## Alternatives 1. [Epos Now](https://www.capterra.ca/software/152638/epos-now) — 3.8/5 (719 reviews) 2. [RetailEdge](https://www.capterra.ca/software/76636/retailedge) — 4.8/5 (186 reviews) 3. [Shopify](https://www.capterra.ca/software/83891/shopify) — 4.5/5 (6690 reviews) 4. [PayPal](https://www.capterra.ca/software/179251/paypal) — 4.6/5 (26419 reviews) 5. [Lightspeed Retail](https://www.capterra.ca/software/120491/lightspeed-retail) — 4.0/5 (975 reviews) ## Reviews ### "My goodness do not buy this software." — 1.0/5 > **Greg** | *June 18, 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 review" — 5.0/5 > **April** | *June 21, 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. ----- ### "Windward System 5 has made running our medium sized dealership much easier" — 5.0/5 > **Trish** | *October 25, 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 ----- ### "Slightly outdated, but intuitive and powerful" — 4.0/5 > **Mason** | *August 1, 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** | *November 13, 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. ----- Page: 1 / 9\ Next: [Next page](https://www.capterra.ca/software/43189/windward-system-five?page=2) ## Links - [View on Capterra](https://www.capterra.ca/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