Windward System Five

Spec sheet

Purpose

Windward System Five combines business management, accounting, inventory control, and point of sale in one system.Read 8 Oct 2026 · windwardsoftware.com

Deployment

System Five is offered as a cloud-hosted SaaS option or as a local installation.Read 8 Oct 2026 · windwardsoftware.com

API

Windward's documentation describes a System Five API with inventory endpoints for external systems.Read 8 Oct 2026 · wiki.windwardsoftware.com

Integrations

Listed integrations include WooCommerce, Shopify, WebSell, Worldpay, Global Payments, ShipRush, Orgill, and Microsoft Power BI via Windward Intelligence.Read 8 Oct 2026 · windwardsoftware.com

Support

Windward says its support staff provide live global support seven days a week.Read 8 Oct 2026 · windwardsoftware.com

Headquarters

Penticton, British Columbia, CanadaRead 28 Sep 2026 · windwardsoftware.com

Founded

1984Read 28 Sep 2026 · windwardsoftware.com

Cloud hosting

System Five on Cloud is hosted on Microsoft Azure and accessed through a virtual desktop; Windward describes continuous backups and encrypted access.Read 8 Oct 2026 · windwardsoftware.com

E-commerce

E-commerce integrations sync online and in-store inventory and can update online pricing and inventory when records change in System Five.Read 8 Oct 2026 · windwardsoftware.com

Inventory

Inventory tools track stock, committed work orders, layaways, and available-to-sell quantities, with up to 99 customer price schedules.Read 8 Oct 2026 · windwardsoftware.com

Inventory management

YesRead 20 Sep 2026 · windwardsoftware.com

Point of sale

Its POS supports barcode scanning, quick cash sales, estimates, work orders, and real-time inventory tracking across stores.Read 8 Oct 2026 · windwardsoftware.com

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.Read 8 Oct 2026 · windwardsoftware.com

Target businesses

Windward describes System Five as serving retail, rental, and service businesses, including sectors such as lighting, powersports, and medical supply.Read 8 Oct 2026 · windwardsoftware.com

Windows support

The System Five Version 7 installation guide lists Windows 10 Pro and Windows 11 Pro among supported operating systems.Read 8 Oct 2026 · support.windwardsoftware.com

Plans and prices

Every Windward System Five plan and price →

Where Specifiction places it

• Point-of-Sale Software#78 of 1137.4
• Retail Management Software#36 of 406.7