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Tech riderRev. 8 Oct 2026

Windward System Five

Ch 587.2of 105 Point-of-Sale Software
  1. 1Runs onAPI, Windows
  2. 2CostsNot stated by the maker
  3. 3Inventory managementYes
2 lines stated Written from the maker's own pages: windwardsoftware.com
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The Windward System Five homepage

Overview

Windward System Five is ranked #58 of 105 in point-of-sale software on Specifiction, made by Windward System Five (Penticton, British Columbia, Canada). It runs on API, Windows.

Windward System Five plans and pricing

All plans
Windward System Five Not published Pricing depends on concurrent users, edition, special features or modules, and local or cloud deployment windwardsoftware.com · 8 Oct 2026

Compared on point-of-sale software

Inventory management
Yeswindwardsoftware.com

Facts

Purpose
Windward System Five combines business management, accounting, inventory control, and point of sale in one system.windwardsoftware.com · 8 Oct 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
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
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
Integrations
Listed integrations include WooCommerce, Shopify, WebSell, Worldpay, Global Payments, ShipRush, Orgill, and Microsoft Power BI via Windward Intelligence.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
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
API
Windward's documentation describes a System Five API with inventory endpoints for external systems.wiki.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
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

Company

Founded
1984windwardsoftware.com · 28 Sept 2026
Headquarters
Penticton, British Columbia, Canadawindwardsoftware.com · 28 Sept 2026

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Where it ranks on Specifiction

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Sources