# icon

> Reviews of Windward System Five. Learn how real users rate this software's ease-of-use, functionality, overall quality and customer support. Talk to our advisors to see if Windward System Five is a good fit for you!

Source: https://www.softwareadvice.com/retail/windward-system-five-profile/reviews/

---

1 million+ businesses helped. Get advice

Get Free Advice

[Home](https://www.softwareadvice.com/)

/

[Retail Management Systems Software](https://www.softwareadvice.com/retail/retail-management-comparison/)

/

[Windward System Five](https://www.softwareadvice.com/retail/windward-system-five-profile/)

/

Windward System Five Reviews

Software Advice offers objective insights based on verified user reviews and independent product and market research. When our advisors match you to a software provider, we may earn a referral fee.

[Overview](https://www.softwareadvice.com/retail/windward-system-five-profile/)

Reviews

[Alternatives](https://www.softwareadvice.com/retail/windward-system-five-profile/alternatives/)

# Windward System Five User Reviews

## Reviews Summary

## Overall Rating

3.8

* * *

## Ratings Breakdown

5

(71)

4

(64)

3

(20)

2

(15)

1

(19)

## Secondary Ratings

Ease-of-use

3.7

Customer Support

3.7

Value for money

3.6

Functionality

3.8

* * *

### Pros

"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."

"It is a different system but once you get to know it and set it up for your business requirements it sets it apart from quickbooks and other accounting software."

"It is easy with Windward for all invoicing."

### Cons

"Very difficult to move away from - their database structure is as well thought out as a dump truck full of spaghetti."

"Very expensive - literally 22.5 TIMES the cost of the software we tried to replace it with."

"not clover integrated- they can't figure out how to get my statements mailed out of the system to clients properly."

* * *

**Weigh the pros and cons with an expert.** Tell an advisor what matters most to you: they'll help you evaluate the pros and cons and narrow down your shortlist.

Narrowing down your options?

Talk to a Retail Management Systems advisor for real-time pricing and tailored feature breakdowns.

Filters

Filter Reviews

[](#product-catalog)

Company Size

-   Self-Employed
    
-   2-10
    
-   11-50
    
-   51-200
    
-   201-500
    
-   501-1,000
    
-   1,001-5,000
    
-   5,001-10,000
    
-   10,000+
    

Time Used

-   Free Trial
    
-   Less than 6 months
    
-   Less than 12 months
    
-   Less than 2 years
    
-   More than 2 years
    

User Rating

-   1 star
    
-   2 stars
    
-   3 stars
    
-   4 stars
    
-   5 stars
    

[Clear](#product-catalog)[Show Results](#)

189 results

Sort by

Windward System Five Reviews, Pros and Cons - 2026 Software Advice