Windward Software

Windward System Five

Composite Score

7.3 /10

CX Score

7.6 /10

14 Reviews Write a Review

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What is Windward System Five?

Windward System Five is a fully integrated point-of-sale solution that helps you manage all your retail operations across the store and your entire business - from the POS to accounting, inventory to purchasing management, financial reporting to customer marketing and management - what's more, it does all these things well!

Company Details

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Awards & Recognition

Windward System Five won the following awards in the Retail POS category

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2024 Emotional Footprint Champion

2024

Strategy and Innovation
Service Experience
Product Impact
Contract Negotiation
Conflict Resolution

2024

2024 Data Quadrant Champion

2024

8 Top Rated Capabilities

2 Top Rated Features

2024

2023 Emotional Footprint Champion

2023

Strategy and Innovation
Service Experience
Contract Negotiation
Conflict Resolution

2023

2023 Data Quadrant Champion

2023

8 Top Rated Capabilities

3 Top Rated Features

2023

Windward System Five Ratings

Real user data aggregated to summarize the product performance and customer experience.
Download the entire Product Scorecard to access more information on Windward System Five.

Product scores listed below represent current data. This may be different from data contained in reports and awards, which express data as of their publication date.

91 Likeliness to Recommend

2
Since last award

93 Plan to Renew

1
Since last award

86 Satisfaction of Cost Relative to Value

1
Since last award

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Emotional Footprint Overview

Product scores listed below represent current data. This may be different from data contained in reports and awards, which express data as of their publication date.

+90 Net Emotional Footprint

The emotional sentiment held by end users of the software based on their experience with the vendor. Responses are captured on an eight-point scale.

How much do users love Windward System Five?

0% Negative

7% Neutral

93% Positive

Pros

Trustworthy
Respectful
Fair
Altruistic

Feature Ratings

Average 81

Sales Transactions

Employee Mobile

Customer Account Management

Analytics and Reporting

Employee Management

Pricing Promotions

PCI and EMV Compatible

Online Integrations Web Store

Cash Register Point of Purchase Devices

Inventory Control

Loyalty Program

Vendor Capability Ratings

Average 80

Ease of IT Administration

Availability and Quality of Training

Business Value Created

Ease of Data Integration

Ease of Implementation

Vendor Support

Breadth of Features

Quality of Features

Product Strategy and Rate of Improvement

Usability and Intuitiveness

Ease of Customization

Windward System Five Reviews

George M.

Role: Operations
Industry: Recreation
Involvement: Business Leader or Manager

Validated Review

Verified Reviewer

Submitted Jun 2025

Great overall software when I used it!

Likeliness to Recommend

8 /10

What differentiates Windward System Five from other similar products?

It consolidates everything you need, including sales, inventory, accounting, and customer tracking, all in one system, so you don’t have to juggle multiple programs.

What is your favorite aspect of this product?

It provides a clear picture of what’s happening in your business, particularly with inventory and sales.

What do you dislike most about this product?

Sometimes, it glitches or slows down after updates, and getting help from support can take some time.

What recommendations would you give to someone considering this product?

Be prepared to learn—it takes some time to get accustomed to it. But if you want one powerful system to run your whole business, it’s worth it. I'd recommend for small and medium-sized businesses like stores, repair shops, rental places, garden centers, and equipment dealers that need strong tools to manage their stock, money, and sales all in one system.

Pros

Efficient Service
Client's Interest First
Generous Negotitation
Over Delivered

Cons

Slower Product Innovation
Less Inspiring

Carla A.

Role: Human Resources
Industry: Transportation
Involvement: IT Leader or Manager

Validated Review

Verified Reviewer

Submitted Jun 2024

a versatile and easy-to-use solution

Likeliness to Recommend

9 /10

What differentiates Windward System Five from other similar products?

Unlike other similar programs, Windward System Five offers a wide range of customizable features that have helped me improve the efficiency of my daily operations.

What is your favorite aspect of this product?

What I like most about Windward System Five is its ability to integrate all areas of my company, from inventory to sales and finance, into one system. This has allowed me to save time and resources by centralizing all the information.

What do you dislike most about this product?

Although there aren't many things I dislike about this software, sometimes the learning curve can be a little steep for less experienced users. However, the support team is always available to help and resolve any questions that may arise.

What recommendations would you give to someone considering this product?

In summary, I would recommend Windward System Five to any company looking for a complete and efficient solution for managing their business. Its capacity for customization, integration and technical support make it stand out from other similar software.

Pros

Continually Improving Product
Performance Enhancing
Enables Productivity
Trustworthy

Role: Operations
Industry: Retail
Involvement: Business Leader or Manager

Validated Review

Anonymous Reviewer

Submitted Jan 2023

A businessman's software. The best!

Likeliness to Recommend

10 /10

Pros

Reliable
Performance Enhancing
Enables Productivity
Unique Features

Windward System Five

What is Windward System Five?

Company Details

Need Assistance?

Awards & Recognition

2024 Emotional Footprint Champion

2024 Data Quadrant Champion

2023 Emotional Footprint Champion

2023 Data Quadrant Champion

Windward System Five Ratings

91 Likeliness to Recommend

2 Since last award

93 Plan to Renew

1 Since last award

86 Satisfaction of Cost Relative to Value

1 Since last award

Emotional Footprint Overview

+90 Net Emotional Footprint

How much do users love Windward System Five?

Pros

Feature Ratings Average rating of all product features, some of which may not be shown below

Sales Transactions Includes an item, quantity, payment, statement of charges/receipt, sales management, refund, exchanges, special order processing and foreign currency/exchange.

Employee Mobile Mobile devices can be used to check inventory, check customer history, and process SALES/RETURN transactions & invoicing.

Customer Account Management Enables customers to charge purchases to an internally regulated in-store charge/credit account, gift cards/certificates.

Analytics and Reporting Includes historical & real-time dashboard visualizations, detailed & summary reporting and easy data extraction for data analysis.

Employee Management Includes employee commission levels, split commission, employee productivity performance, discount limits, workforce rostering & scheduling.

Pricing Promotions Includes a price, label, an intrinsic value, markdowns, promotional scheduling, bundling, discounting and activation rules engine, customer specific pricing.

PCI and EMV Compatible Includes system monitoring, remote access control, security alarms, and sensors.

Online Integrations Web Store The solution provides or integrates with and supports online sales channels/webstore and marketplaces (i.e. Amazon) and unified inventory.

Cash Register Point of Purchase Devices Includes cash drawer, POS terminal, customer display, bar code scanner, card reader, receipt printer that can operate with or without network connectivity.

Inventory Control Includes open-to-buy, unit/SKU availability, tracking, purchasing, automatic replenishment, backorder status, stock counts, receipt planning, product history.

Loyalty Program Provides or integrates with loyalty, reward and relationship management programs for customer marketing, demographics, targeted up/cross-sell, coupons & points.

Vendor Capability Ratings Average rating of all vendor capabilities, some of which may not be shown below

Ease of IT Administration This data indicates whether IT personnel will be able to resolve issues and perform configurations efficiently and effectively.

Availability and Quality of Training Effective and readily available training enables users to get the most out of the software you've chosen. Use this section to make sure your vendor's training programs and materials measure up.

Business Value Created Software needs to create value for employees, customers, partners, and, ultimately, shareholders. This data expresses user satisfaction - or lack thereof - with the product's business value.

Ease of Data Integration Use this data to determine whether the product will cause headaches or make data integration easy.

Ease of Implementation Successfully implementing new software is necessary to realize its full value and promote end user adoption. This data indicates whether or not the product is easy to implement.

Vendor Support The importance of vendor support will vary for each organization depending on internal capabilities, but there will always be issues that only the vendor can resolve.

Breadth of Features Users prefer feature rich software that enables them to perform diverse series of tasks. This data expresses user satisfaction with the product's breadth of features.

Quality of Features Feature quality is just as important as quantity. Use this data to determine if this product will do what you're purchasing it to do, easily, intuitively, reliably, and effectively.

Product Strategy and Rate of Improvement Vendors who don't stay on top of emerging needs and trends won't enable you to meet your business goals. Use this data to separate innovators from imposters.

Usability and Intuitiveness End user learning curves cost the organization money. Pay attention to your end users' technical ability to determine how important UX is in your purchase.

Ease of Customization Don't get bogged down in a difficult customization; use this data to make sure you can easily achieve the functionality you need for your particular situation.

Windward System Five Reviews

George M.

Great overall software when I used it!

Likeliness to Recommend

Pros

Cons

Carla A.

a versatile and easy-to-use solution

Likeliness to Recommend

Pros

A businessman's software. The best!

Likeliness to Recommend

Pros

2
Since last award

1
Since last award

1
Since last award

Feature Ratings

Sales Transactions

Employee Mobile

Customer Account Management

Analytics and Reporting

Employee Management

Pricing Promotions

PCI and EMV Compatible

Online Integrations Web Store

Cash Register Point of Purchase Devices

Inventory Control

Loyalty Program

Vendor Capability Ratings

Ease of IT Administration

Availability and Quality of Training

Business Value Created

Ease of Data Integration

Ease of Implementation

Vendor Support

Breadth of Features

Quality of Features

Product Strategy and Rate of Improvement

Usability and Intuitiveness

Ease of Customization