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About Windward System Five

Founded in 1984, Windward Software specializes in real time inventory management and point-of-sale software solutions for retail businesses and the customer service sector. The company is headquartered in Penticton, British Columbia and also maintains offices in Dallas, Chicago, Brisbane, the Philippines, South Africa, the United Arab Emirates and Bermuda. Windward Software products are used by many companies across the globe.

Windward System Five point-of-sale software includes all the capabilities one expects in a retail management software package. Designed for independent retailers, this POS software system provides modules for cash sales, bar code scanning, inventory management, customer data input, layaways, account payments and billing, credits and returns and work orders. Windward System Five offers flexibility when generating invoices and receipts, including customized layouts; the ability to edit, correct and reprint; automated inclusion of appropriate taxes; and discounting, both on an entire order or on a single line item. This point-of-sale system is highly flexible and uses a number of “soft switches” that enable Windward to offer customized installations for a wide array of specialties in the retail industry. Additionally, a mobile app for Android devices is available, enabling users to conduct transactions in the field. Maintenance packages, training videos, and live support are also available.

(Last updated on 03/21/2016)

Windward System Five User Reviews

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Bushido C.

Bushido Enterprise Ltd.

Windward System 5

Ease of Use
Reviewed on October 11, 2017

What do you like best about this product?

The sales aspect. Easy to find and select items. Reporting scores 7/10. Support is generally good. Training modules available.

What could be improved about this product?

Financials need a major overhaul. Very outdated and cumbersome. Not comparable to Quickbooks. If you feel QB is not suitable enough for your business then this definitely wont. They could integrate with QB even at an extra cost. Some software functionality does not work in other areas in the software when it should.

What was your main concern about buying this software?

Financials and many bugs. They don’t fix them or listen or feel they are important enough to address.

What business problems are you solving? What benefits have you seen?

Sales aspect is good. Easy to add items to work order. Software is stable meaning it does not crash. Otherwise no major benefits or enhancements to our old software.

How likely would you be to recommend this software to a friend or colleague?


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