Rain POS vs Windward System Five

Shopify

Square Point of Sale

Fishbowl

Shopify POS

STORIS

EBMS

Compare Rain POS and Windward System Five based on features, pricing, verified reviews, integrations & more on GetApp. Find out which software is best for your business in 2026.

Square Point of Sale is a POS solution for Android and iOS devices which includes tools for managing payments, digital receipts, inventory, reports, and more.

Shopify Point of Sale (POS) is a retail management system that integrates everything needed to run a successful brick-and-mortar or omnichannel business. The POS software and hardware work seamlessly together to streamline daily operations, from inventory management and staff controls to smooth checkout and detailed reporting.

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

Rain is a cloud-based point-of-sale system designed to help retailers save time and sell more by seamlessly integrating in-store inventory with eCommerce websites.

Accounting Integration

Activity Tracking

Alerts/Notifications

Barcode/Ticket Scanning

Catalog Management

Consignment Management

Cost Tracking

Credit Card Processing

Customer Accounts

Customer Database

Customer Management

Customizable Fields

Customizable Reports

Data Import/Export

Data Security

Discount Management

eCommerce Management

Electronic Payments

Electronic Signature

Email Marketing

For Retail

For Small Businesses

Forecasting

Gift Card Management

Inventory Auditing

Inventory Control

Inventory Management

Inventory Optimization

Inventory Tracking

Invoice Management

Item Management

Kitting

Label Printing

Layaway Management

Loyalty Program

Manufacturing Inventory Management

Merchandise Management

Mobile Access

Mobile Commerce

Multi-Channel Management

Multi-Channel Marketing

Multi-Currency

Multi-Location

Multi-Store

Order Management

Order Processing

Order Tracking

Ordering Automation

Payment Options

Payment Processing

Point of Sale (POS)

Point of Sale (POS) Integration

Pricing Management

Product Catalog

Product Configurator

Product Identification

Promotions Management

Purchase Order Management

Real-Time Reporting

Real-Time Updates

Receipt Management

Reorder Management

Reordering

Reporting & Statistics

Reporting/Analytics

Retail Inventory Management

Retail Management

Retail POS

Returns Management

Returns Tracking

Reviews Management

Sales Order Management

Sales Reports

Sales Tax Management

Search/Filter

SEO Management

Shipping Management

Shopping Cart

Social Media Integration

Supplier Management

Templates

Third-Party Integrations

Touch Screen

Transaction History

User Management

Website Management

Rain POS

Web-based

Windows

Manager

Their support has continued long after the initial onboarding and I feel very confident in their ability to help us whenever we hit a roadblock and need help.

President

Website build out is horribly confusing and NOTHING follows traditional HTML processes. This was the same problem with Lightspeed's eCom platform - hard to work with and no sense of workflow.

Owner/Manager

First line support staff is very helpful and relatively easy to reach. Sales staff makes lots of lofty promises that are slow to be fulfilled.

Owner 

Unable to add shipping charges to individual items that are bulky.

co-owner

The ease of this software is very important. Being a small business i really don't have an I.T department so you guessed it we all become the I.T department in our office.

Owner

I like the fact that it is cloud based so we can add another register as needed during very busy times. Also the integration between the website and the POS is great for product inventory.

Coordinator

The website builder is so bad that I am looking for another alternative but the initial setup fee was so high it really does sting to switch to another provider (maybe that was the point).

Ease of use and customer service are absolutely superb.

General Manager/Owner

The efficiency I've gained by using this software versus going other routes has completely justified the value for me and my business.

They have always been there for me and are so nice, especially when trying to set up my website. I am not a computer genius and don't have to be because I use Rain.

I love that Checker Distribution & United Notions are integrated with Rain Retail.

At times the system has quirks that are an annoyance to the user and is a low priority fix for developers.

I had trouble with my labels in the printing mode. I use a different size of label than they have on file.

The customer service is amazing, and I have always been able to solve any problems I’ve had with one phone call.

Rental, class, and automatically populating the website is a big help for us saving time. It hasn't really made us more money as advertised.

Once you learn the system and features, it's pretty easy and intuitive.

The integration of product sku codes, inventory, customer tracking, re-order points, everything was top notch and an added value for the cost.

The site is a little laggy to start and then everything works super fast. Most things in this realm are intuitive.

Rain POS screenshot

Rain POS screenshot: Rain POS Checkout Page

Rain POS screenshot: Rain POS Marketing Dashboard

Freelancers

Mid Size Business

Small Business

We make business growth easier by putting ERP software to work. EBMS allows you to effortlessly manage all of your operations in one place—connecting business financials to labor management, inventory control, sales and everything in between.

Designed with simplicity and efficiency in mind, Fishbowl’s complete manufacturing and inventory management solution transforms the inventory process and uses automation to help growing businesses make strategic and precise decisions based on real-time data and cut costs.

STORIS is an all-in-one retail software suite for home furnishings, bedding, and appliance retailers. It integrates POS, inventory, order management, eCommerce, and distribution in one platform, helping businesses streamline operations and deliver a seamless omnichannel customer experience.

Windward System Five is a cloud-based business management solution designed to help small to midsize organizations streamline the processes related to point of sale (POS), inventory control, enterprise resource planning (ERP), customer relationship management (CRM), payments, rentals, and more.

Asset Tracking

Barcode Recognition

Barcoding/RFID

Billing & Invoicing

Cash Management

Commission Management

Contract/License Management

Customer History

Document Management

Document Storage

Employee Management

For Liquor Stores

Inspection Management

Maintenance Management

Price/Margin Management

Real-Time Data

Reservations Management

Scheduling

Utilization Reporting

Warehouse Management

Windward System Five

Android

Linux

Once live, it just got worse and worse. In hindsight, I should have listened to my gut in implementation, written the money invested off as a bad business decision and aborted.

So much stress that my whole team went through only to end up worse off. Before we went live, in my gut I had doubts due to my experience with Windward staff in the lead up transition period.

Partner and General Manager

When we have to call for tech support we have to talk to someone over seas and most of the time our connections are terrible. Hard to hear or understand and calls are dropped.

Office manager

I like how it is inventory control and accounting integrated into one system. The system has great abilities.

Sales/Reception

One of these incidents has caused irreparable harm to our business relationship with our (previously) largest customer.

Owner, Director of Operations

It truly has the ability to accommodate anything I want to do to operation my business more efficiently. System Five is a very user friendly product that is easy to learn and understand.

Great customer service and great software. Can do pretty much everything you need for you business.

CFO and Owner

We have been using the software now for 3 months and, after WW helps us to get a few kinks ironed out with the software, we will be very happy with the software.

 Owner

I lost a feature to my program due to a bug problem....1 year later it is fixed but requires another upgrade to get it back.

Amazing inventory control and accounting is up to date without costing a fortune in labour or software.

owner

Stay Away, poor Company and Poor program full of glitches.

Partner

Another thing I like about Windward is the quality of  Windward's support.

Our overall experience was extremely poor and detrimental to our business.

Bookkeeper

When we integrated with online sales we found it very frustrating because it was not as easy as we were made to think it was.

Accounts Receiable

Overall it has been pretty easy to learn this program.

The program lacks in the accounting and reporting area. Daily closeout and accounting reports are difficult to work with if you are using an outside accounting package.

Controller

Moving the data from our old system to Windward was very easy. We were able to import with very little mistakes.

General Manager

Nationwide Furniture Mattress Outlet looks forward to continuing and growing our partnership with Windward Software.

Rain POS vs Windward System Five Comparison (2026)

Rain POS

Windward System Five

Overview

Video & Screenshots

Pricing

User reviews

Key features

Integrations

Alternatives