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Windward System Five

What Windward System Five is
Windward System Five combines business management, accounting, inventory control, and point of sale in one system for retail, rental, and service businesses. Its POS supports barcode scanning, cash sales, estimates, and work orders, with real-time inventory tracking across stores. Inventory tools track stock, committed work orders, layaways, and available-to-sell quantities, and allow up to 99 customer price schedules. The system also offers multi-location support, employee management, customer profiles, purchase orders, and custom reporting.
E-commerce integrations can synchronize online and in-store inventory, and changes to System Five records can update online prices and stock. Listed integrations include WooCommerce, Shopify, WebSell, Worldpay, Global Payments, ShipRush, Orgill, and Microsoft Power BI through Windward Intelligence. Buyers can choose cloud-hosted SaaS or local installation. The cloud option runs on Microsoft Azure and is accessed through a virtual desktop; Windward describes continuous backups and encrypted access. A System Five API provides inventory endpoints for external systems. Windward, founded in 1984 and based in Penticton, British Columbia, Canada, says its support staff provide live global support seven days a week. Pricing is on request and depends on users, edition, modules, and deployment choice.
Who it suits
System Five suits retail, rental, and service businesses that need point of sale alongside accounting, business management, and inventory control. It is relevant to organizations managing multiple locations or syncing store inventory with e-commerce systems.
What it does well
- Combines point of sale, accounting, inventory, and business management.
- Tracks stock, work orders, layaways, and available-to-sell quantities.
- Supports up to 99 customer price schedules.
- E-commerce integrations synchronize online and in-store inventory.
- Offers cloud-hosted SaaS or local installation.
What to know first
- Pricing is available on request and varies by configuration.
- The listed platforms are Windows and API.
Limits
Pricing varies with concurrent users, edition, required features or modules, and local or cloud deployment; buyers must contact Windward for specific pricing.
Plans
| Plan | Billed and limits | Price |
|---|---|---|
| Windward System Five | Pricing depends on concurrent users, edition, special features or modules, and local or cloud deployment | On request |
As windwardsoftware.com lists them, read 8 Oct 2026. The maker's own page has the final word.
Getting started
- Visit the Windward System Five website.
- Contact Windward for pricing based on users, edition, modules, and deployment.
- Choose cloud-hosted SaaS or local installation.
- For a local installation, check the listed Windows 10 Pro and Windows 11 Pro support.
- Use the System Five API inventory endpoints if connecting an external system.
Verdict
Consider System Five if your retail, rental, or service operation needs inventory management and point of sale in one system, with cloud or local deployment. Look elsewhere if you need a published price or a platform beyond Windows and API.
Questions
How much does Windward System Five cost?
It is paid, with pricing on request. The price varies by concurrent users, edition, features or modules, and local or cloud deployment.
Can I choose cloud or local deployment?
Yes. System Five is offered as cloud-hosted SaaS or as a local installation.
Which platforms are listed?
The listed platforms are Windows and API.
What e-commerce integrations are listed?
The maker lists WooCommerce, Shopify, and WebSell, alongside payment, shipping, and other integrations.
Does the cloud option include backups?
Windward describes continuous backups and encrypted access for its Microsoft Azure-hosted cloud option.
What types of businesses does System Five serve?
Windward describes it for retail, rental, and service businesses, including lighting, powersports, and medical supply sectors.
Facts from Windward System Five's own pages
- API
- Windward's documentation describes a System Five API with inventory endpoints for external systems. · wiki.windwardsoftware.com, 8 Oct 2026
- Cloud hosting
- System Five on Cloud is hosted on Microsoft Azure and accessed through a virtual desktop; Windward describes continuous backups and encrypted access. · windwardsoftware.com, 8 Oct 2026
- Deployment
- System Five is offered as a cloud-hosted SaaS option or as a local installation. · windwardsoftware.com, 8 Oct 2026
- E-commerce
- E-commerce integrations sync online and in-store inventory and can update online pricing and inventory when records change in System Five. · windwardsoftware.com, 8 Oct 2026
- Founded
- 1984 · windwardsoftware.com, 28 Sept 2026
- Headquarters
- Penticton, British Columbia, Canada · windwardsoftware.com, 28 Sept 2026
- Integrations
- Listed integrations include WooCommerce, Shopify, WebSell, Worldpay, Global Payments, ShipRush, Orgill, and Microsoft Power BI via Windward Intelligence. · windwardsoftware.com, 8 Oct 2026
- Inventory
- Inventory tools track stock, committed work orders, layaways, and available-to-sell quantities, with up to 99 customer price schedules. · windwardsoftware.com, 8 Oct 2026
- Inventory management
- Yes · windwardsoftware.com, 20 Sept 2026
- Point of sale
- Its POS supports barcode scanning, quick cash sales, estimates, work orders, and real-time inventory tracking across stores. · windwardsoftware.com, 8 Oct 2026
- Pricing
- The FAQ says pricing varies with concurrent users, edition, required features or modules, and local versus cloud deployment, and directs buyers to contact Windward for specific pricing. · windwardsoftware.com, 8 Oct 2026
- Purpose
- Windward System Five combines business management, accounting, inventory control, and point of sale in one system. · windwardsoftware.com, 8 Oct 2026
- Support
- Windward says its support staff provide live global support seven days a week. · windwardsoftware.com, 8 Oct 2026
- Target businesses
- Windward describes System Five as serving retail, rental, and service businesses, including sectors such as lighting, powersports, and medical supply. · windwardsoftware.com, 8 Oct 2026
- Windows support
- The System Five Version 7 installation guide lists Windows 10 Pro and Windows 11 Pro among supported operating systems. · support.windwardsoftware.com, 8 Oct 2026
Where Windward System Five stands on Freedom251
- Point-of-Sale Software#83 of 113
- Retail Management Software#36 of 40