Windward System Five vs Retail Pro Comparison: Everything You Need to Know Before Choosing

Windward System Five is a comprehensive business management system from Windward Software, a Canadian vendor, built for companies that sell, service or rent inventory. Businesses such as hardware stores, equipment dealers, automotive parts suppliers and service shops often juggle separate systems for point of sale, inventory, accounting and service work, leading to duplicated data entry, inaccurate stock levels and limited visibility into profitability. Windward System Five addresses this by combining these functions into a single integrated system that covers the full operational cycle, from purchasing and receiving stock through to selling, servicing, renting and accounting. Its approach reflects decades of experience with inventory-intensive businesses, offering deep configurability so that the system can support varied workflows, and combining traditional on-premise reliability with options for remote and cloud access. The breadth of the system means a single database underpins the whole business, reducing reconciliation work between departments. Key modules include point of sale with barcode scanning and integrated payments, inventory management with multiple locations, serialised items, reorder points and supplier catalogues, and purchasing and receiving workflows. Service and repair functionality supports work orders, labour tracking and technician scheduling, while rental management covers contracts, availability and returns. Built-in accounting includes general ledger, accounts receivable and payable, and financial reporting, with the option to integrate with other accounting tools. Customer management, loyalty programmes and marketing features help build repeat business, and extensive reporting provides insight into sales, margins and stock turnover. E-commerce integration enables businesses to synchronise inventory with online stores. System Five can be deployed on-premise or hosted in the cloud, and Windward provides training and implementation support. Target customers include independent retailers, hardware and building supply stores, equipment dealers, marine and powersports businesses, and service companies across North America. Pricing starts from around USD 155 with a free trial; there is no permanently free version.