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Toast POS vs Windward System Five

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Updated February 5, 2026

Toast 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
$69.00

per month

$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
Cash Management
4.93
Reporting & Statistics
4.83
Order Tracking
4.50
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Retail Management
4.33
Sales Reports
4.24
Product Identification
4.14
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Integrations
QuickBooks Online Advanced
QuickBooks Online Advanced
TapMango
TapMango
SynergySuite
SynergySuite
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Worldpay for Enterprise
Worldpay for Enterprise
Descartes ShipRush
Descartes ShipRush
See All
Pros / Cons
  • The aspects I enjoy about Toast POS is the security, card payment options, mobile access, and restaurant management options.
  • The toast system also blocks many QR code/mobile order payments for no apparent reason, which Toast states is a bug they’re working on, but of course, I never received answers for questions I posed on this matter.
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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
3.8/ 5
3.6/ 5
Customer Support
3.7/ 5
3.7/ 5
Functionality
Highest performing feature
in the comparison
4.1/ 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
74 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