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Retail Management Software
Windward System Five reviews and summary
Windward System Five on Cloud is a comprehensive, fully-integrated Enterprise Resource Planning (ERP) system built for businesses that deal with physical inventory, particularly in sales, service, and rental. It unifies all core operational modules—including Point of Sale (POS), Customer Relationship Management (CRM), advanced Inventory Management, and robust Accounting—into a single, real-time platform. This deep integration ensures that a transaction at the counter instantly updates stock levels, customer history, and financial ledgers. The system is notably flexible, with features and configurations that cater to a wide array of specialty retail and rental verticals, s... This system is designed for established small to large businesses and chains...
Best for
This system is designed for established small to large businesses and chains in the retail, rental, and service sectors that require a unified management solution. It is ideal for owners and managers of hardware stores, equipment rental yards, garden centers, and specialty retailers who need tight integration between their front-counter sales, back-office inventory, and financial systems to operate efficiently and ga...
Starting price
$129.00 Per-Month
Category
Retail Management Software
Vendor
Windward Software
Key takeaways
Our verdict
Our verdict is that Windward System Five on Cloud is a powerful and mature ERP solution that delivers exceptional value through its real-time, fully-integrated architecture. Its vertical-specific flexibility and scalability make it a formidable choice for inventory-centric businesses seeking to eliminate data silos, streamline complex operations, and gain a holistic, accurate view of their business performance across all departments.
Quick facts
Windward System Five at a glance
Overall rating
3.8/5
Reviews
147
Starting price
$129.00 Per-Month
Vendor
Windward Software
Founded
1984
Location
Canada
Category
Retail Management Software
Ratings
Windward System Five ratings
Ratings in this section summarize available rating data. Software reviews are shown separately when users submit reviews.
Decision notes
Windward System Five pros and cons
Potential strengths
- Combines POS, CRM, inventory, and accounting, which may reduce duplicate work for businesses that sell, service, or rent physical stock.
- Targets inventory-focused retail and wholesale teams, including use cases such as home goods, outdoor power equipment, rental, and garden centers.
- Supports single-location shops and larger chains, so buyers can assess it against both current operations and planned growth.
- Lists cloud, Windows desktop, on-premise Windows and Linux, and Android support, giving teams several deployment and device paths to review.
Points to verify
- Map a full sales, service, or rental transaction before purchase to see whether POS, inventory, and accounting updates behave as expected.
- Confirm whether the configuration fits your vertical market without too much custom setup or process compromise.
- Check mobile needs carefully, since Android is listed but iPhone and iPad are not listed as enabled.
- Ask how training and support work for multi-location rollouts, role permissions, and day-one data migration.
Buyer fit
Who uses Windward System Five?
This system is designed for established small to large businesses and chains in the retail, rental, and service sectors that require a unified management solution. It is ideal for owners and managers of hardware stores, equipment rental yards, garden centers, and specialty retailers who need tight integration between their front-counter sales, back-office inventory, and financial systems to operate efficiently and ga...
Feature research
Windward System Five features
These are common features buyers compare in Retail Management Software. Product-specific availability should be confirmed with the vendor.
Sales Commission Tracking
Monitor sales commissions and incentive earnings for staff members.
CRM Integration
Sync with CRM systems to centralize customer data and streamline business relationships.
E-Commerce Integration
Seamless synchronization and management of data between the platform and online retail systems.
Email Campaign Management
Design and distribute bulk email communications and targeted marketing campaigns.
Workforce Management
Monitor staff scheduling, work availability, and individual performance metrics.
Customer Loyalty Programs
Enable customers to accumulate points for repeat business that can be redeemed for future discounts.
Postal Product Ordering
Streamline product ordering and postal delivery procedures.
Inventory Procurement Intelligence
Offers insights for informed inventory procurement choices.
Multi-Site Management
Support for organizations operating across multiple physical sites or stores.
Order Lifecycle Management
Supervise the lifecycle of customer orders from initial request through to final execution for various assets.
PO Management
Generate, transmit, and monitor the fulfillment status of purchase orders.
Reports & Analytics
Analyze and visualize essential performance metrics and data trends.
Pricing
Windward System Five pricing
Starting price
$129.00 Per-Month
Visit Website
Pricing model: Per User
Pricing can change. Confirm current plans and terms with the vendor.
Compare
Windward System Five alternatives
Compare Windward System Five with other Retail Management Software tools that buyers often evaluate.
Ricochet by Ricochet
An iPad-native POS system purpose-built for consignment and thrift stores that need to track inventory and payouts across multiple consignors. It bundles point-of-sale, ecommerce,...
Retail Pro by Retail Pro International
Retail Pro is a highly flexible, device-agnostic software platform designed for specialty retail management on a global scale. It provides a powerful suite of tools encompassing Po...
POSIM by Retail Success
POSIM, from Retail Success, is a robust, hosted on-site retail management solution that has been serving brick-and-mortar stores for over three decades. It is explicitly designed f...
Storepoint by Storepoint
Storepoint is a dedicated service for adding a fully customized, interactive store locator to a business website. The platform is designed for ease of use, promising setup in just...
RICS Software by RICS Software
RICS Software is a specialized Point-of-Sale and Inventory Management platform exclusively designed for retailers in the APPAREL, FOOTWEAR, and ACCESSORY sectors. It provides a foc...
PawnMaster by Data Age Business Systems
PawnMaster is the industry-leading software for pawnshops, built with nearly 30 years of feedback from pawn brokers. It simplifies operations to reduce costs and maximize cash flow...
Wireless Standard POS by B2B Soft
Wireless Standard POS by B2B Soft is a robust, cloud-based point of sale system engineered specifically for the wireless retail industry. It provides a comprehensive suite of tools...
Software reviews
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FAQ
Windward System Five FAQs
Windward System Five is used as a business management system for companies that sell, service, or rent inventory. It brings POS, CRM, inventory, and accounting into one operating setup.
The profile points to small and medium retail or wholesale companies with physical inventory. Mentioned examples include home goods, outdoor power equipment, rental businesses, and garden centers.
Yes. The product information describes use by both single-location shops and national chains. Buyers should still confirm location controls, reporting, and inventory transfers for their own setup.
The listed core functionality includes Point of Sale, CRM, Inventory, and Accounting. That combination is most relevant when teams want fewer gaps between front-counter work and back-office records.
The profile lists Cloud, SaaS, Web-Based access, Desktop Windows, on-premise Windows and Linux, and Mobile Android. Desktop Mac, Desktop Linux, Chromebook, iPhone, and iPad are not listed as enabled.
Buyers should verify transaction flow, inventory accuracy, accounting handoff, device support, and setup effort for their specific retail, rental, or service workflow.
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