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Shopify POS vs Windward System Five

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Updated March 2, 2026

Shopify POS vs Windward System Five: Which is best for you?

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55+ software advisors
1 million+ businesses helped
2 million+ verified software reviews
Starting Price
$5.00

per month

$135.00

per month

Free Trial
Free Version
Screenshots
and Demo
Product Screenshot
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Product Screenshot
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Top Rated
  Features
Data Synchronization
4.86
Mobile Access
4.74
Retail Management
4.71
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Retail Management
4.33
Sales Reports
4.24
Product Identification
4.14
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Integrations
Meta for Business
Meta for Business
Shopify
Shopify
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Worldpay for Enterprise
Worldpay for Enterprise
Datacap
Datacap
WooCommerce
WooCommerce
See All
Pros / Cons
  • Users highly value that inventory, customer data, and sales are automatically synchronized across all channels, eliminating the need to manually reconcile stock or customer records.
  • SHOPIFY POS IS AWFUL --- The receipt printer and barcode scanners disconnect daily and Shopify support is completely useless to fix this despite thousands of merchants discussing it in their forums.
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  • My overall experience was positive, and still is to some extent, though we largely use System Five as a database for older customer information now.
  • Very difficult to move away from - their database structure is as well thought out as a dump truck full of spaghetti.
Read more
Ease-of-Use
Highest performing feature
in the comparison
4.6/ 5
3.7/ 5
Value for Money
Highest performing feature
in the comparison
4.3/ 5
3.6/ 5
Customer Support
Highest performing feature
in the comparison
4.4/ 5
3.7/ 5
Functionality
Highest performing feature
in the comparison
4.5/ 5
3.8/ 5
Support Options
Email/Help Desk
FAQs/Forum
Knowledge Base
Phone Support
24/7 (Live Rep)
Chat
Email/Help Desk
FAQs/Forum
Knowledge Base
Phone Support
24/7 (Live Rep)
Chat
Training Options
In Person
Live Online
Webinars
Documentation
Videos
In Person
Live Online
Webinars
Documentation
Videos
FrontRunners
FrontRunners 2025
N/A
Advisor
  Recommendations
N/A
N/A
Ideal Customer Size
Small
Medium
Large
Small
Medium
Large
Deployment Options
Cloud, SaaS, Web-Based
Desktop - Mac
Desktop - Windows
Desktop - Linux
Desktop - Chromebook
On-Premise - Windows
On-Premise - Linux
Mobile - Android
Mobile - iPhone
Mobile - iPad
Cloud, SaaS, Web-Based
Desktop - Mac
Desktop - Windows
Desktop - Linux
Desktop - Chromebook
On-Premise - Windows
On-Premise - Linux
Mobile - Android
Mobile - iPhone
Mobile - iPad