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Windward System Five
Based on GetApp‘s extensive, proprietary database of in-depth, verified user reviews
Cloud-based business management solution | ERP for your SMB
Table of Contents
Is this product right for your business?
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Windward System Five - 2026 Pricing, Features, Reviews & Alternatives
All user reviews are verified by in-house moderators and provider data by our software research team. Learn more
Windward System Five overview
What is Windward System Five?
Windward System Five is a cloud-based business management solution designed to help small to midsize organizations streamline the processes related to point of sale (POS), inventory control, enterprise resource planning (ERP), customer relationship management (CRM), payments, rentals, and more. The platform allows users to create a customer database that improves their sales and marketing capabilities. Windward System Five on Cloud enables enterprises to manage the entire business process lifecycle, from sales and invoicing to promotions, delivery scheduling, customer service, and marketing. Features include barcoding, digital signature capture, multi-store management, serial number tracking, payroll, budgeting, and more. The automated accounting system allows managers to view and update journal entries and the general ledger as well as print balance sheets, statements, and pending payments reports. Besides, the email marketing tool comes with customizable templates, which lets businesses create white-label marketing campaigns to promote their products and services. Windward System Five’s reporting functionality helps enterprises to generate a variety of reports for profit and loss statements, inventory, purchases, and more. Plus, users can automate the posting of recurring entries for upcoming months. The solution integrates with various third-party applications such as ShipRush, MultiCat Reporting, Polaris, and Worldpay.
Who uses Windward System Five?
By industry, Windward System Five reviewers are most commonly professionals in retail (50%). The most frequent use case for Windward System Five cited by reviewers is retail inventory management (68% of reviewers).
What do users say about Windward System Five pricing?
Some users say Windward System Five offers competitive pricing and good value due to integrated services. However, some reviewers feel the system is pricey, with high maintenance costs and additional charges that can burden small businesses.
Starting price
per month
Alternatives
with better value for money
Pros & Cons
Stockkeeping
Functionality
Scalability
Responsiveness
Stability
Revisions
Windward System Five’s user interface
Windward System Five pros, cons and reviews insights
To determine these pros and cons insights, we analyzed responses from
Overall rating
Value for money
3.6
Features
3.8
Ease of use
3.7
Customer support
3.8
Reviews sentiment
What do users say about Windward System Five?
Reviewers indicate Windward System Five offers robust inventory management, integrated accounting, and extensive reporting tools, which help streamline retail and sales operations. They appreciate its customizable interface and flexibility for different business types, finding the point-of-sale and order processing features useful for daily tasks. Most say support is friendly and responsive, especially for urgent issues, and value the regular updates and cloud option for easier maintenance.
Users report frequent bugs, glitches, and slow updates, with some finding the help documentation lacking and upgrades introducing new problems. They mention high costs for support and add-ons, and note that reporting and customization can be complex and time-consuming.
Select to learn more
Who uses Windward System Five?
Based on 189 verified user reviews.
Company size
Small Businesses
Enterprises
Midsize Businesses
Top industries
Use cases
Windward System Five's key features
Most critical features, based on insights from Windward System Five users:
All Windward System Five features
Features rating:
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Windward System Five pricing
Pricing plans
Pricing details:
User opinions about Windward System Five price and value
Value for money rating:
Of 22 reviews that provide robust commentary on Windward System Five's price and value, 36% mention it in a positive light.
Some users say Windward System Five offers competitive pricing and comprehensive integration of necessary services, making it a good value for money. They appreciate its ease of use, ability to import/export data, and automatic price updates. However, some reviewers feel the system is pricey, with high maintenance and updating costs. They report issues with pricing matrices, import inconsistencies, and additional costs for certain features. Users also mention that the cost of the system and associated expenses can be a significant hurdle, especially for small businesses.
, and
To see what individual users think of Windward System Five's cost and value, check out the review excerpts below.
Marie V.
Owner/Operator
Windward System Five integrations (3)
Integrations rated by users
We looked at 189 user reviews to identify which products are mentioned as Windward System Five integrations and how users feel about them.
Integration rating: 5.0 (1)
Integration rating: 4.0 (1)
Other top integrations
Windward System Five customer support
What do users say about Windward System Five customer support?
Customer support rating:
We analyzed 69 verified user reviews to identify positive and negative aspects of Windward System Five customer support.
A number of users highlight the 24/7 availability and prompt response times from Windward's support team.
Multiple users appreciate the knowledgeable, friendly staff who go the extra mile to resolve issues and support business needs.
A portion of users report inconsistent support quality, with some staff lacking expertise or providing only temporary fixes.
Multiple users mention long wait times, expensive support fees, and challenges reaching or communicating with overseas support.
Support options
Training options
To see what individual users say about Windward System Five's customer support, check out the review snippets below.
“Windward returns calls, answers questions, owns up if the issue is on their end, finds acceptable temporary workarounds, and makes me feel that my business success is important to them. ”
Karen D.
Owner
“The customer service and technical support are extremely prompt and never fail to provide us with a resolution to any problems we have had.”
Trish H.
Administrator
“We were never given true solutions, only band aids and work arounds. If your issues are not a priority, you will wait in the queue while others are dealt with. Upon the demo and trial version, we asked what the refund policy was, we followed the protocol and asked for a refund being that even a clean slate install was producing errors.”
Michael M.
Windward System Five FAQs
Windward System Five has the following pricing plans:
Starting from: $155.00/month
Pricing model: Subscription
Free Trial: Available | (No Credit Card required)
These products have better value for money
Q. What are the benefits of using Windward System Five?
Buy better, market smarter and work more efficiently in your business. Windward System Five provides you with the knowledge and control to drive profits.
Control your inventory, track inventory movement, optimize stock levels and improve your cost control measures through reports.
Create a database with your customer information to provide a smoother, more personal shopping experience, and increase your selling and marketing opportunities.
Windward Software's integrated accounting software allows you to view, print, enter and report data quickly and conveniently, providing and simple, error-free way of managing your books.
Empower your employees with the access and information they need to perform their jobs properly, without compromising security or confidential data.
Q. Who are the typical users of Windward System Five?
Windward System Five has the following typical customers:
Freelancers, Large Enterprises, Mid Size Business, Small Business
Q. What languages does Windward System Five support?
Windward System Five supports the following languages:
English
Q. Does Windward System Five support mobile devices?
Windward System Five supports the following devices:
Android
Q. Does Windward System Five offer an API?
Yes, Windward System Five has an API available for use.
Q. What other apps does Windward System Five integrate with?
Windward System Five integrates with the following applications:
Worldpay for Enterprise, Descartes ShipRush
Q. What level of support does Windward System Five offer?
Windward System Five offers the following support options:
24/7 (Live rep), Knowledge Base, Chat, Email/Help Desk, Phone Support, FAQs/Forum
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