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Epos Now vs Windward System Five

Updated February 9, 2026

Epos Now 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
$349.00

one time

$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
Order Processing
4.86
Touch Screen
4.72
Transaction Monitoring
4.50
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Retail Management
4.33
Sales Reports
4.24
Product Identification
4.14
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Integrations
Deputy
Deputy
Salesforce Sales Cloud
Salesforce Sales Cloud
Eventbrite
Eventbrite
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Worldpay for Enterprise
Worldpay for Enterprise
Descartes ShipRush
Descartes ShipRush
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Pros / Cons
  • Epos Now is a top-tier POS solution that blends flexibility, ease of use, and powerful integrations—ideal for businesses seeking a customizable, cloud-based system. If you’re looking for a point-of-sale system that adapts to your business rather than the other way around, Epos Now deserves serious consideration.
  • The system fails in many ways for the industry being tailored to a retail point of sale "payment at purchase" model - and every time I have raised a deficiency in the system for my industry I am simply told "that is the way it works" and that I can make a request for change.
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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
3.8/ 5
3.7/ 5
Value for Money
3.6/ 5
3.6/ 5
Customer Support
3.6/ 5
Highest performing feature
in the comparison
3.7/ 5
Functionality
3.7/ 5
Highest performing feature
in the comparison
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 2022
N/A
Advisor
  Recommendations
37 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