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Shopify vs Windward System Five Comparison (2026)

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Good recommendations?

Shopify

Windward System Five

Overview

Shopify is a commerce platform that allows anyone to easily sell online, at a retail location, and everywhere in between

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.

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

No videos yet

Pricing

Starting from

Per month

Free trial available
Credit cardless trial
Free account
Subscription based

Starting from

135

/user

Per month

Free trial available
Credit cardless trial
Free account
Subscription based

User reviews

4.5

6.7K

4.3K

1.9K

348

Value for money

Ease of use

Features

Customer support

77%

would recommend this app

3.8

189

Value for money

Ease of use

Features

Customer support

53%

would recommend this app

Pros

“I use it to sell photography albums, and it provides a professional checkout experience, secure payment processing, and multiple payment options for clients.”

michael k.

President

“We use Shopify for new webshop builds, redesigns, replatforming projects, migrations and ongoing webshop optimization.”

Simon A.

Founder and Shopify E-commerce Strategist at Opklopper

“Our experience is that Shopify gives growing brands a reliable foundation for product management, checkout, payments, shipping, content, tracking, apps, integrations and international growth.”

Simon A.

Founder and Shopify E-commerce Strategist at Opklopper

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

Cons

“Monthly subscription that can strain cash flow at launch, some third-party apps get expensive quickly, advanced customization requires coding knowledge.”

Nicole T.

Event Marketing and Operations

“Another minor frustration is that certain features and reports are only available on higher-tier plans, which can make it difficult for smaller businesses to access the tools they need without upgrading.”

Gary A.

Founder CEO

“The discount code system is pretty basic - we can't do the tiered pricing structures our bulk buyers expect without workarounds.”

Andy C.

Sales Director

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