Windward System Five vs LS Retail

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.

fairly easy to use- good customer service -

Co-Owner

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

Windward System Five is integrated accounting software that connects general ledger, AR/AP, and bank reconciliation directly to your point of sale, inventory, and CRM. Built for independent retailers, wholesalers, service, and rental businesses ready to retire month-end reconciliation for good.

Access Controls/Permissions

Accounting

Accounting Integration

Accounts Payable

Accounts Receivable

Activity Dashboard

Age Verification

Alerts/Notifications

Asset Lifecycle Management

Asset Tracking

Availability Indicator

Availability Management

Bank Reconciliation

Barcode Recognition

Barcode/Ticket Scanning

Barcoding/RFID

Billing & Invoicing

Budgeting/Forecasting

Calendar Management

Cash Flow Management

Cash Management

Chart of Accounts

Check-in/Check-out

Commission Management

Contract/License Management

Cost Tracking

Credit Card Processing

Currency Conversion

Customer Accounts

Customer Database

Customer History

Customer Management

Customizable Fields

Customizable Reports

Data Import/Export

Data Synchronization

Discount Management

Document Management

Document Storage

eCommerce Management

Electronic Signature

Email Marketing

Employee Management

Expense Tracking

Financial Management

Financial Reporting

Fixed Asset Management

Fleet Management

Forecasting

For Liquor Stores

For Retail

General Ledger

Gift Card Management

Income & Balance Sheet

Inspection Management

Inventory Management

Inventory Optimization

Inventory Replenishment

Inventory Tracking

Invoice Management

Item Management

Layaway Management

Loyalty Program

Maintenance Management

Maintenance Scheduling

Merchandise Management

Multi-Channel Management

Multi-Currency

Multi-Location

Ordering Automation

Order Management

Order Processing

Order Tracking

Payment Processing

Point of Sale (POS)

Price/Margin Management

Pricing Management

Product Catalog

Product Identification

Project Management

Promotions Management

Purchase Order Management

Purchasing & Receiving

Quotes/Estimates

Real-Time Analytics

Real-Time Data

Real-Time Monitoring

Real-Time Reporting

Real-Time Updates

Receipt Management

Reorder Management

Reporting/Analytics

Reporting & Statistics

Reservations Management

Retail Inventory Management

Retail Management

Retail POS

Returns Management

Proprietary

Windward System Five

Web-based

Windows

System Five on Cloud with Partner Processing

System Five on Cloud Standard

System Five on Cloud Monthly

Frequent bugs disrupt workflow

89% of reviewers feel negative about Windward’s bugs and issues. Some users report encountering persistent system errors, glitches, and crashes that disrupt daily operations and make tasks like reconciling accounts or processing transactions difficult. Reviewers indicate that unresolved bugs can linger for months, causing frustration and inefficiency. They say frequent problems with modules such as multi-currency and back orders, as well as slow loading times, contribute to a sense of unreliability. Users think these recurring technical issues undermine their confidence in the software’s stability.

Slow and inconsistent support experience

46% of reviewers feel negative about Windward’s customer support. Some users say support responses are slow, with long wait times for callbacks or issue resolution, especially for urgent problems. Reviewers indicate that support staff often lack the expertise to resolve complex issues, leading to temporary fixes rather than lasting solutions. They report frustration with offshore support centers, expensive service fees, and a lack of accountability from management. Users feel that poor communication and inadequate assistance can leave critical business problems unresolved for extended periods.

Comprehensive inventory control tools

82% of reviewers feel positive about Windward’s inventory management. Reviewers indicate the system offers detailed tracking for stock levels, pricing, and reorder needs, which they find crucial for managing a large variety of products from multiple suppliers. Some users say the ability to import and export data with Excel streamlines pricing updates, while others appreciate the robust reporting features for analyzing inventory and sales trends. They find that having integrated modules for sales, purchasing, and accounting helps them maintain accurate records and improves efficiency in daily operations.

Sales Associate

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

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.

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.)

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.

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.

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)

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.

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.

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

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

So many extra features here that make it so helpful.

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.

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.  

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.

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.

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.

i still find it hard to navigate and find stuff.

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

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.

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.

President

The integrated CRM is very useful for keeping track of appointments and follow ups.

With Windward we are able to use the reports to budget for the future, look at our sales history per customer, get customer reports that we need.

Understanding more about the system prior to set up would have helped.  

With more staff, this system would be absolutely amazing.  

Positive, but can be frustrating when it errors.

Not to mention that one (1) IT support person worked night shift and would call us at 9:00 pm Eastern Time for us to login the system so he could troubleshoot!

V.P.

The built in reports allowed for easily customizing reports.

Office Manager/ Owner

There are many features that could be incredibly useful.

Set multiple selling prices, build kits out of existing parts.

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

Sales/Reception

The ability to print count sheets with only product in stock - no part numbers with a "zero" quantity, is great and saves paper.  

Customer Support

Features

Pricing

Sales Reporting

Tracking and Organization

Ease of Use

Reporting

User Interface

Training and Learning Curve

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.

A unified ERP + POS software solution built on Microsoft Dynamics technology that is ideal for retailers, restaurants, hotels, pharmacies and gas stations with at least 50+ employees, or multiple locations. Ideal also for companies with ambitious growth goals.

Windward System Five vs LS Retail Comparison (2026)

Windward System Five

LS Retail

Overview

Video & Screenshots

Pricing

User reviews

Key features

Integrations

Alternatives