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Rain POS vs Windward System Five

Updated December 15, 2025

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

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1 million+ businesses helped
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Starting Price

Pricing available upon request

$131.00

per month

Free Trial
Free Version
Screenshots
and Demo
Product Screenshot
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Product Screenshot
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Top Rated
  Features
Product Identification
5.0
Shopping Cart
4.92
Reorder Management
4.86
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Retail Management
4.33
Sales Reports
4.24
Product Identification
4.14
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Integrations
Avalara
Avalara
ShipStation
ShipStation
TaxJar
TaxJar
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Worldpay for Enterprise
Worldpay for Enterprise
Descartes ShipRush
Descartes ShipRush
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Pros / Cons
  • They set up my website as close as they could match to my previous one from Wix and they did a pretty good job (although I discovered some mistakes that were pretty bad, such as the wrong phone number for my store, they were easily fixed by me) but I am frightened of doing anything to it beyond changing the text.
  • The Sales Tax report is the worst, it does not break out non taxable items you must report in Colorado.
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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.
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Ease-of-Use
Highest performing feature
in the comparison
4.2/ 5
3.7/ 5
Value for Money
Highest performing feature
in the comparison
4/ 5
3.6/ 5
Customer Support
Highest performing feature
in the comparison
4.1/ 5
3.7/ 5
Functionality
Highest performing feature
in the comparison
3.9/ 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 2023
N/A
Advisor
  Recommendations
48 Recommendations
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