Windward System Five
Windward System Five: A broad retail system for Windows retailers that need accounting, inventory, and multi-store control. Ranked #22 of 38 in Retail Management Software by our editors (7.2/10); pricing: Pricing on request; best for windows retailers needing accounting integration.
At a glance
- Editor score7.2 / 10
- PricingPricing on request
- Best forWindows retailers needing accounting integration
- Multi-location supportYes
- Founded1984 · Penticton, British Columbia, Canada
- Facts checked20 Sep 2026
Where it wins
- Combines POS, inventory, purchasing, accounting, and reporting
- Supports multi-store transfers and centralized retail operations
- Offers ecommerce integrations and a web API with multiple endpoints
Where it doesn't
- Windows-only platform limits device and operating-system flexibility
- Contact-sales pricing provides limited upfront cost visibility
- Its broad feature set may exceed the needs of smaller retailers
Our verdict on Windward System Five
Windward System Five combines point of sale, inventory control, purchasing, customer management, accounting, reporting, and ecommerce capabilities in one retail management platform. It is designed for independent retailers, specialty stores, service businesses, rental businesses, and organizations operating multiple locations. Windows retailers that need general ledger functions alongside store operations will find the product’s scope particularly relevant, while businesses seeking broad device or operating-system coverage may need to look elsewhere.
The system covers core retail workflows from barcode-based inventory tracking and invoicing to purchase orders, automated purchasing, customer histories, serial-number inventory, and consignment inventory. Multi-store inventory transfers and centralized operations support organizations with more than one location. Reporting spans financial, customer, inventory, and custom outputs, giving retailers room to shape reporting around their operations. Local installation and cloud deployment are both supported, and ecommerce synchronization connects the retail system with WebSell, WooCommerce, and Shopify. Payment and business integrations include NETePay, Global Payments, Worldpay, AVB LINQ, and Microsoft Power BI.
Pricing is quote-based rather than presented as fixed public plans. The vendor describes pricing as dependent on users, modules, edition, and local versus cloud deployment, so the buying process centers on matching the configuration to the retailer’s requirements. The web API adds endpoints for customers, inventory, invoices, vendors, and other areas, which can support connections beyond the listed integrations. Windward System Five is a strong fit for Windows retailers that want one system spanning store transactions, inventory, purchasing, accounting, and multi-location management. Retailers prioritizing transparent plan pricing, broad platform coverage, or a narrower point-of-sale tool should consider alternatives.
Your product? Our editors can test Windward System Five in depth and publish a review, labelled as paid · from $149/mo →
Windward System Five pricing
Windward System Five fact sheet
| Free plan | Not verified |
|---|---|
| Paid from | Not verified |
| Multi-location support | Yes |
| Inventory management | Yes |
| Employee management | Yes |
| Customer profiles | Yes |
| Purchase orders | Yes |
| API access | Yes |
| Reporting level | Custom |
| Deployment | Cloud, Self-hosted, Desktop |
| Platforms | Windows |
| Support | Email, Phone, Docs |
| Built for | Small business, Mid-market, Enterprise (editorial estimate) |
| Integrations | 8 integrations: WebSell, WooCommerce, Shopify, AVB LINQ, NETePay, Global Payments … See all → |
| Pricing | Pricing on request |
| Website | windwardsoftware.com |
| Facts checked | 20 Sep 2026 |
Windward System Five integrations
Windward System Five lists 8 integrations on its own site.
- WebSell
- WooCommerce
- Shopify
- AVB LINQ
- NETePay
- Global Payments
- Worldpay
- Microsoft Power BI
See all Windward System Five integrations →
Alternatives to Windward System Five
- SAP RetailA broad SAP retail suite for complex merchandise and supply chain operations.9.4
- Cegid RetailA broad retail platform for connected stores, inventory, fulfillment, and customer engagement.9.3
- Oracle Retail Xstore Point-of-ServiceA broad enterprise POS covering store operations, inventory, workforce, and omnichannel orders.9.2
See all Windward System Five alternatives →
Also Ranked In
Windward System Five is ranked in 3 of our directories.
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Reviewed by iTechGuides Editors · Editorial team · Updated Oct 2026
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