Windward System Five
Retail POS and business management for stores and multi-location retailers.
At a glance
- Editor scoreNot yet scored
- 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.
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
- Lightspeed RetailA broad retail platform for multi-location operations, with higher-tier reporting and API access.5.3
- SAP RetailA broad SAP retail suite for complex merchandise and supply chain operations.7.0
- Cegid RetailA broad retail platform for connected stores, inventory, fulfillment, and customer engagement.—
See all Windward System Five alternatives →
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Reviewed by iTechGuides Editors · Editorial team · Updated Sep 2026
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