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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
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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
Last updated: March 2026
Windward System Five overview
What is Windward System Five?
Windward System Five is a fully integrated business management platform designed for independent and growing businesses with complex operational needs. It combines point of sale (POS), inventory management, CRM, and accounting into a single system, providing a consistent and accurate data foundation across the organization. System Five supports end‑to‑end operational workflows, including purchasing and receiving, multi‑location inventory management, work orders and special orders, invoicing, and accounts receivable. The platform is highly configurable, allowing businesses to adapt pricing, inventory structures, workflows, and permissions to match real‑world operations rather than forcing process changes to fit the software. Native reporting is extended through Windward Intelligence, an optional analytics layer that delivers KPI dashboards and performance visibility across sales, margins, customers, and operational trends. This enables managers and owners to move beyond static reports and monitor business health in near real time. For businesses selling both in‑store and online, Windward System Five integrates with WebSell for e‑commerce. Product, pricing, and customer data remain synchronized, and online orders are processed using the same fulfillment, invoicing, and accounting workflows as brick‑and‑mortar transactions—simplifying omnichannel operations and reducing manual work. Windward System Five is supported by personalized onboarding, training, and ongoing support, making it a strong fit for organizations that value flexibility, long‑term scalability, and direct access to knowledgeable product experts.
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
Tracking and Organization
Reporting
Training and Learning Curve
Customer Support
Pricing
Customization
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?
Development is out of control - one developer in one area will fix something but that will break 4 other things in other areas.
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:
Windward System Five alternatives
Windward System Five
Starting from
135
/user
Per month
Epos Now
Starting from
No pricing info
Shopify
Starting from
No pricing info
RetailEdge
Starting from
No pricing info
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 (5)
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: 4.0 (1)
Integration rating: 1.0 (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 typical customers:
Freelancers, Small Business
These products have better value for money
Q. What are the benefits of using Windward System Five?
Operate from a single source of truth:
Unify point of sale, inventory, CRM, and accounting in one platform to eliminate duplicate data, manual work, and disconnected systems.
Handle complex operations with confidence:
Support purchasing, receiving, multi‑location inventory, work orders, special orders, invoicing, and accounts receivable using configurable workflows that adapt to your business—not the other way around.
Gain visibility with real business insights:
Go beyond static reports with Windward Intelligence, an optional KPI dashboard that provides at‑a‑glance visibility into sales performance, margins, customer trends, and operational health.
Simplify omnichannel selling:
Integrate with WebSell to keep product and customer data synchronized across in‑store and online sales. Process web orders using the same fulfillment, invoicing, and accounting workflows as brick‑and‑mortar transactions.
Flexible functionality with integrated add‑ons:
Windward System Five offers a strong core platform with optional, internally developed add‑ons that extend functionality as your needs grow—so you can expand capabilities without relying on disconnected third‑party tools.
Scale with personalized support:
Get hands‑on onboarding, training, and ongoing support from a team that understands your industry and long‑term growth needs.
Q. What languages does Windward System Five support?
Windward System Five supports the following languages:
English
Q. Does Windward System Five offer an API?
Yes, Windward System Five has an API available for use.
Q. What level of support does Windward System Five offer?
Windward System Five offers the following support options:
24/7 (Live rep), Knowledge Base, Email/Help Desk, Phone Support, FAQs/Forum
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