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Overview

Windward System Five helps businesses streamline operations with integrated POS, inventory management, and detailed reporting. While advanced analytics are limited, it delivers robust tools for multi-store retail, distribution, and specialty sectors. Its real-time reporting and operational visibility ensure better decision-making and smoother workflow across teams.

Overall Rating

Based on 5 users reviews

3.6

Rating Distribution

Positive

60%

Neutral

20%

Negative

20%

Starting Price
Custom

Windward System Five Specifications

  • Financial Management
  • Inventory Management
  • Customer Relationship Management
  • Sales And Marketing Automation
View All Specifications

What Is Windward System Five?

Windward System Five is a full-featured ERP solution designed for small and mid-sized businesses. It combines POS, inventory management, barcoding, and financial reporting tools within a single platform. Users can track sales, monitor inventory, and generate detailed reports to optimize operational efficiency. The software is especially beneficial for multi-store retail and distribution companies, helping reduce errors, improve stock control, and gain insights for better business decisions. Its features enable centralized control over workflows, inventory, and customer data, improving overall productivity and operational accuracy.

How Much Does Windward System Five Cost?

Windward Software price is estimated to start at $155.00/user/month. Its plans can be customized to meet the unique requirements of different organizations.

In addition to the base license or subscription costs, organizations should account for the following potential expenses:

  • Implementation: $5,000–$50,000, depending on business size and deployment complexity
  • Data Migration And Integrations: $5,000–$30,000, depending on legacy data and integration scope
  • Training And Onboarding: $750–$5,000 for staff training packages
  • Additional Modules/User Add-ons: $1,000–$5,000 per module, or $40–$200+/user/month for cloud subscriptions
  • Annual Maintenance/Support: 15–25% of license cost per year, or included in subscription plans
For accurate pricing based on your organization’s needs, it’s recommended to request a custom Windward Software pricing estimate.

Disclaimer: Pricing references are based on publicly available third-party information and industry benchmarks. Actual costs may vary.

Windward System Five Integrations

The software integrates with different third-party systems, including:

  • Microsoft Power BI
  • WooCommerce
  • WebSell
  • Liquor Connect
  • Ship Rush
Book a free Windward System Five demo to learn more about its integration arrangements.

Who Is Windward System Five For?

Windward System Five is ideal for businesses across various industries and sectors, including:

  • Appliance
  • Retail
  • Furniture
  • Automotive

Is Windward System Five Right For You?

Windward System Five is well-suited for SMBs seeking an all-in-one ERP solution with integrated POS, inventory management, and reporting capabilities. It caters to multi-store retail and distribution businesses, offering flexible deployment and fail-safe technology. Its customizable reporting and business analysis tools make it an excellent fit for companies aiming to streamline operations and drive growth.

Still doubtful if Windward System Five is the right fit for you? Connect with our customer support staff at (661) 384-7070 for further guidance.

Windward System Five Features

Point Of Sale

Windward System Five enhances customer engagement and boosts sales with tools for transaction management, signature capture, and seamless checkout processes. It supports multi-register setups, loyalty program tracking, and integrates with inventory to ensure consistency across locations.

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Inventory Control

It tracks inventory movement, optimizes stock levels, and improves cost management to reduce waste. Users can set reorder alerts, monitor trends, and automate stock transfers, preventing stockouts and overstock situations across multiple stores.

See How It Works
Financial Reporting

This feature generates detailed P&L statements balance sheets, and customized reports for financial oversight. Businesses can analyze sales trends, monitor expenses, and export data to support audits, planning, and strategic decision-making.

See How It Works
Customer Management

Windward System Five creates detailed customer profiles to improve service quality, marketing campaigns, and overall engagement. Tracking purchase history, preferences, and promotions enables personalized interactions, loyalty growth, and repeat business.

See How It Works

Pros And Cons of Windward System Five

Pros

  • Strong inventory management and purchasing capabilities

  • Real-time inventory tracking improves accuracy

  • Integrated accounting saves time on financial tasks

Cons

  • Form creation can be complex and time-consuming

  • Initial setup can be confusing without proper understanding

Windward System Five Reviews

Total 5 reviews

3.6

All reviews are from verified customers

Rating Distribution

5

Stars

40%

4

Stars

20%

3

Stars

20%

2

Stars

0%

1

Stars

20%

Share your experience

MB

Mason B.

Consumer Goods, N/A employees

Less than a year

4.0
August 2025

strong features and great value

Pros

Value is really good and the software turned out to be much more capable than I expected. It handles inventory tracking, private customer information management and invoicing very well.

Cons

The interface feels outdated and buggy which makes it harder to take full advantage of everything it can do. It also has occasional long loading times, plus those notifications about users connected to different hardware can get pretty annoying.

Rating Distribution

Ease of use

7

Value for money

6

Customer Support

9

Functionality

8

GH

Greg H.

Retail, N/A employees

More than a year

1.0
June 2025

expensive mess with awful support

Pros

There's no denying System Five is incredibly versatile and packed with functionality. If you need a feature, it probably already has it. The interface is great and since we run it on-premises, performance is usually acceptable, although with more than 20 years of accumulated data some reports have started to run slowly.

Cons

At the same time, almost nothing seems to function the way it should. The support has been terrible at every level and the pricing is outrageous, literally 22.5 times higher than the software we tested as a replacement. On top of that, getting away from it is incredibly difficult because the database structure feels completely chaotic, like a dump truck full of spaghetti. Trying to export our data has been an absolute nightmare.

Rating Distribution

Ease of use

1

Value for money

1

Customer Support

1

Functionality

2

SH

Shauna H.

Retail, N/A employees

More than a year

5.0
November 2024

flexible setup and POS-friendly platform

Pros

Compared with QuickBooks and other accounting programs, this one feels different but that difference really works in its favor once it's set up around your business needs. After you learn how it works, it stands out clearly, especially because it fits POS use much better than many traditional accounting systems.

Cons

One issue is the bugs that sometimes cause the system not to update properly. It also leans more toward being POS-friendly than accounting-focused. Without a great understanding of how it works, it can create problems in the data so stronger training would help a lot, especially for long-time older users who may still struggle with the system.

Rating Distribution

Ease of use

10

Value for money

10

Customer Support

8

Functionality

8

Frequently Asked Questions

What languages does Windward System Five support?

Windward System Five is primarily available in English.

Does Windward System Five offer an API?

Yes, API access is available for advanced integrations.

What level of support does Windward System Five offer?

Support includes phone, email, academy, and customer care portal.

Who are the typical users of Windward System Five?

Windward System Five features are suitable for different industries and sectors, including retail, appliance, furniture, and industrial supplies.

What types of pricing plans does Windward System Five offer?

The software’s price is estimated to start at $155.00/user/month. Its plans can be customized to meet the unique requirements of different organizations. Get in touch for a tailored Windward System Five cost estimate.

Does Windward System Five have a mobile app?

Yes, it offers a mobile app called Windward System Five Sidekick.

What other apps does Windward System Five integrate with?

It integrates with different third-party apps, such as Microsoft Power BI, WooCommerce, WebSell, Liquor Connect, and Ship Rush.