Windward System Five vs WooPOS

Epos Now

Shopify

RetailEdge

Epos Now is a leading global cloud-based point-of-sale and payment system that specializes in helping US retail and hospitality businesses trade efficiently.

Thanks to a selection of tools, and an extensive app store, users can create bespoke systems that make running a business simple.

Shopify is a commerce platform that allows anyone to easily sell online, at a retail location, and everywhere in between

RetailEdge is a point of sale solution that helps retail businesses manage inventory and sales orders. Key features of the platform include barcode scanning, item listing, customer history tracking, credit card processing, price management, invoicing, secure data storage, and gift card distribution.

owner

It then seemed the support workers did not know windward very well and I was brushed off or it would take a long time to resolve the issue.  

Owner

Development is out of control - one developer in one area will fix something but that will break 4 other things in other areas.

From finding customer to products ,it has a report for everything.

fairly easy to use- good customer service -

Windward System Five on Cloud is a full business management system for companies that sell, service, or rent inventory. The software includes core functionality of Point of Sale, CRM, Inventory and Accounting; operating in real time, fully integrated.  Windward is the ERP of choice for your SMB.

Access Controls/Permissions

Accounting Integration

Activity Dashboard

Age Verification

Alerts/Notifications

Asset Lifecycle Management

Asset Tracking

Availability Indicator

Availability Management

Barcode Recognition

Barcode/Ticket Scanning

Barcoding/RFID

Billing & Invoicing

Calendar Management

Cash Management

Commission Management

Contract/License Management

Cost Tracking

Credit Card Processing

Customer Accounts

Customer Database

Customer History

Customer Management

Customizable Reports

Data Import/Export

Data Synchronization

Discount Management

Document Management

Document Storage

eCommerce Management

Electronic Signature

Email Marketing

Employee Management

Forecasting

For Liquor Stores

For Retail

Gift Card Management

Inspection Management

Inventory Management

Inventory Optimization

Inventory Replenishment

Inventory Tracking

Invoice Management

Item Management

Loyalty Program

Maintenance Management

Maintenance Scheduling

Merchandise Management

Multi-Channel Management

Multi-Currency

Multi-Location

Ordering Automation

Order Management

Payment Processing

Point of Sale (POS)

Price/Margin Management

Pricing Management

Product Catalog

Product Identification

Promotions Management

Purchase Order Management

Quotes/Estimates

Real-Time Analytics

Real-Time Data

Real-Time Monitoring

Real-Time Reporting

Real-Time Updates

Receipt Management

Reporting/Analytics

Reporting & Statistics

Reservations Management

Retail Inventory Management

Retail Management

Returns Management

Returns Tracking

Sales Order Management

Sales Reports

Sales Tax Management

Sales Trend Analysis

Scheduling

Search/Filter

Shipping Management

Stock Management

Supplier Management

Third-Party Integrations

Touch Screen

Transaction History

Utilization Reporting

Warehouse Management

Work Order Management

Proprietary

Windward System Five

Web-based

Windows

Linux

WooPOS

2-10 Users

11-20 Users

21+ Users

Frequent software errors and glitches

89% of reviewers feel negative about Windward’s bugs and issues. Users report encountering persistent system errors, glitches, and crashes during daily operations, which disrupt business activities and cause frustration. Some reviewers say problems like programming errors, slow loading times, and unresolved bugs are common, with support tickets often remaining open for extended periods. They find that recurring technical issues make certain features unreliable or difficult to use, and mention that documentation is often incomplete or unhelpful. Users express concern that these ongoing problems negatively impact their ability to efficiently manage business processes.

Inconsistent and slow support experience

46% of reviewers feel negative about Windward’s customer support. Users report frequent delays in receiving help, especially for urgent issues, and say they often wait for callbacks or face long hold times. Some reviewers find support staff lack product knowledge, leading to unresolved problems or only temporary fixes. They indicate frustration with offshore support centers, high costs for assistance, and difficulty reaching knowledgeable personnel. Users mention that communication gaps and lack of follow-through from account managers contribute to ongoing dissatisfaction, with some feeling their concerns are not taken seriously or adequately addressed.

Comprehensive inventory control tools

82% of reviewers feel positive about Windward’s inventory management. Users think the system offers detailed and flexible inventory tracking, allowing them to easily monitor stock levels, manage pricing, and generate comprehensive reports. Reviewers appreciate the ability to import and export data with Excel, which streamlines bulk updates and vendor management. Some users say real-time inventory updates and integrated accounting features save significant time in daily operations. They find the software’s reporting and tracking capabilities help them stay organized and maintain better control over inventory, making it easier to reorder products and analyze sales trends.

PARTS MANAGER

Currently I can set up different percentages based on supplier, sub category and others, BUT I am unable to set a pricing matrix with varying percentages for an increasing cost value.

Sales Associate

Capable with inventory tracking, private customer data management, and invoicing.

The interface is good, we host on premises so performance is generally OK (after 20+ years our dataset is getting big and some reports are slow.)

Accounts Payable Manager and Bookkeeping Assistant

The system is more POS friendly than accounting friendly. If you do not learn about the system, it can mess up the information more so there needs to be better training especially for the older users that have been using the system for a long time.

It has been great learning a new system and tailoring it to the needs of my bosses and the business.

The learning I have been able to gain from the videos and training I attended have helped.

The software seems able to do nearly anything necessary, except for a few odds and ends like creating a report for a single salesperson for a set date period for each supplier, for SPIFF purposes.

So many extra features here that make it so helpful.

glitches in the system for inventory control, does not count correctly stock constantly out

Owner 

When we first took over this long-time local business, previous owners did most reports or tracking by hand (ie hand-written invoices entered into QB and hand-written price books)

As business exploded we were able to keep up to the  increases in stock levels,expected stock and tagging stock already on order for specific clients.

Owner/operator

Inventory from multiple suppliers with barcodes have to be entered in as coming from one main supplier with all other suppliers entered in as alternates.

Controller

System is basically garbage in - garbage out, meaning if you provide correct data, it will give you accurate information and results.

We do not currently use the accounting portion, but hope to move over to the accounting option with the new data set.  

At first I was intimidated by how exact you have to be when some of the wording is ambiguous, but once you learn what the system means/wants, its a breeze and has saved us tens of hours already.

general set up and viewing of invoices, customer info section needs to be bigger.

The barcode can't have any supplier attached to it or my computer makes a loud beep.  

Example, sending a paystub to the wrong employee, in clearing an item for years ago, just weird random error messages.

V.P.

The built in reports allowed for easily customizing reports.

Windward API was very limited to what info could be pushed and pulled from the website.

The amount of tabs, and vernacular used, often make it more difficult to do a simple operation.

general manager 

We would like to see regular scheduled maintaince as part of our annual subscription plan.

The system is very user friendly for the basic user and with a little experience on it you can become a whiz quickly Inventory tracking when used correctly is awesome!!

Accounting Manager

It seems that you only get to upgrade to a new version if you complain about functionality not working.  

About 2.5 months in, and a good portion was correcting issues that we didn't have time to fix before going live.  

Sales & Service Manager

Windward fits us great, the cloud system was a very important consideration for remote accessibility.  

Clitches, slow, trade ins difficult, doesn’t round on account payments

The ease of entering sales. Once the model number is in the system, everything is very fluid.

Looks like there are alot of good options to use in this system, but maybe have not been set up yet for us.

Co-Owner

Those items remain outstanding as support is unable to address them.

Purchasing Officer

There is a lot of potential however I was not shown this at the start of the switch over.

PURCHASER

Every feature seems to tap out in functionality.

Corporate Secretary/Business Manager

The answer was for me to send the the spreadsheets after setting them up and work 40 + hours attending to my business.

Some times it takes so long to get the support we need.  

i still find it hard to navigate and find stuff.

Bookkeeper

The customer support could be better with assistance.

Manager

Any negatives are more nit-picking issues.

At the beginning 12+ years ago it worked ok for me. But over the years as prices rose.

I think with a more comprehensive set-up program this system would be easier to use.

Glitches include BUT WERE NOT LIMITED TO: mixing up data across customer records showing machines that belonged to other customers on accounts (nothing to with our data); showing bills and outstanding amounts for other customers on accounts; continuously locking our staff out; full system outage; slowing down sales; daily sales reports inaccurate; export reports missing data.

manager/it

We have solved issues with double ordering Special Orders, have streamlined Purchase Orders, Receiving, Price Changes, Showroom tag printing.

Customer Support

Features

Online Support

Pricing

Reporting

User Interface

Training and Learning Curve

Customization

Among reviewers who comment on Windward System Five's customization, 43% feel negative. Users say it offers extensive options for custom and pre-built reports, flexible exports, and real-time visibility. However, they report that creating and modifying reports is often cumbersome, slow, and sometimes inaccurate, with missing or malfunctioning features.

Sales Reporting

Small Business

Freelancers

Windward Software

PayPal

PayPal provides an end-to-end suite of tools that can integrate with a business's existing systems and service providers. Its network of shoppers and businesses provides AI-driven data insights to help businesses reach new customers and drive results.

Digital Operations Manager

Customer support is absolutely incredible compared to other systems. When we have an issue, it is generally fixed within an hour.

Sales

This has allowed us to track the front ends repair time with various skus and customer labels.

WooPOS -- Point of sale and inventory management for WooCommerce and Shopify. Fit businesses for up to 1000 employees and 1M products. Customizable for all types of retail Industries. Hybrid online and offline database, 500 comprehensive analytics reports.

Windward System Five vs WooPOS Comparison (2026)

Windward System Five

WooPOS

Overview

Video & Screenshots

Pricing

User reviews

Key features

Integrations

Alternatives