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Windward System Five vs WooPOS Comparison (2026)

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Good recommendations?

Windward System Five

WooPOS

Overview

Windward System Five on Cloud is a complete retail management system that brings POS, inventory, purchasing, CRM, and accounting into one platform — built for independent retailers running real, often complex, operations. Single store to multi-location, specialty catalogs to high-volume retail.

WooPOS -- Point of sale and inventory management for WooCommerce and Shopify. Fit businesses for up to 1000 employees and 1M products. Customizable for all types of retail Industries. Hybrid online and offline database, 500 comprehensive analytics reports.

Platforms supported

Web-based
iPhone app
Android app
Windows Phone app

Typical customers

Freelancers
Small businesses
Mid size businesses
Large enterprises

Customer support

Phone
Online
Knowledge base
Video tutorials

view more detailsview details

Platforms supported

Web-based
iPhone app
Android app
Windows Phone app

Typical customers

Freelancers
Small businesses
Mid size businesses
Large enterprises

Customer support

Phone
Online
Knowledge base
Video tutorials

view more detailsview details

Video & Screenshots

Pricing

Starting from

135

/user

Per month

Free trial available
Credit cardless trial
Free account
Subscription based

Starting from

/user

Per month

Free trial available
Credit cardless trial
Free account
Subscription based

User reviews

3.8

189

Value for money

Ease of use

Features

Customer support

53%

would recommend this app

4.6

185

117

Value for money

Ease of use

Features

Customer support

84%

would recommend this app

Pros

“Capable with inventory tracking, private customer data management, and invoicing.”

Mason B.

Sales Associate

“The interface is good, we host on premises so performance is generally OK (after 20+ years our dataset is getting big and some reports are slow.)”

Greg H.

Owner

“It has been great learning a new system and tailoring it to the needs of my bosses and the business.”

Shauna H.

Accounts Payable Manager and Bookkeeping Assistant

Pros

“Woo is an extremely robust system that has seemingly unlimited potential for customization, which is exactly what we needed. While researching a new system, we were amazed to find how homogeneous most solutions were, offering absolutely no flexibility for more complex business needs.”

Lauren D.

Brand and Marketing Director

“This has allowed us to track the front ends repair time with various skus and customer labels.”

Makayla O.

Sales

“WooPOS is very to easy to use and extremely flexible to meet our specific needs.”

SAEED S.

Accounting Manager

Cons

“The system is more POS friendly than accounting friendly. If you do not learn about the system, it can mess up the information more so there needs to be better training especially for the older users that have been using the system for a long time.”

Shauna H.

Accounts Payable Manager and Bookkeeping Assistant

“Currently I can set up different percentages based on supplier, sub category and others, BUT I am unable to set a pricing matrix with varying percentages for an increasing cost value.”

Jeff G.

PARTS MANAGER

“Development is out of control - one developer in one area will fix something but that will break 4 other things in other areas.”

Greg H.

Owner

Cons

“One challenge with Woo is that it cannot be run on mac operating systems, which was admittedly a bit of a hurdle for us (though a solution is in the works to my understanding!).”

Lauren D.

Brand and Marketing Director

“There is a lot that you can translate, invoices, the POS to be easily used. But sometimes it can create bugs on normal operation when trying to translate some strings like in the day/end tab.”

Francois S.

President

“The POS software we previously used did not have nearly the customizability that Woo has.”

Jen C.

Store Manager