Windward System Five 2026: Benefits, Features & Pricing

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Overview
Pricing and Plans
Features
Integrations
User Reviews

Overview

Windward System Five

3.8

(189)

Pricing

Starting at $135.00 per month

About Windward System Five

Windward System Five is a comprehensive business management solution designed for independent and growing businesses that need more than basic point‑of‑sale software. It combines POS, inventory management, CRM, and accounting into a single, integrated system—eliminating data silos and giving teams a clear, real‑time view of their operations.

With System Five, businesses can manage purchasing and receiving, track inventory across locations, process work orders and special orders, invoice customers, and handle accounts receivable from one platform. Flexible configuration options support complex inventory, pricing, and workflows, making it a strong fit for retail, wholesale, and service‑based operations.

Built‑in reporting is enhanced with Windward Intelligence, an optional KPI dashboard that helps owners and managers monitor sales performance, margins, customer trends, and operational health at a glance.

For businesses selling both in‑store and online, System Five integrates with WebSell to support e‑commerce. Product and customer data stay in sync, and online orders can be processed using the same workflows as in‑store transactions, simplifying omnichannel operations.

Windward S...

Windward System Five Screenshots

Windward System Five Pricing and Plans

Starting price: $135.00 per month

Free Trial

Free Version

2-10 Users

$155.00

per user, per month

Plan includes:

24/7 Live Customer Support
2-Factor Authentication
Add Ons – Advanced Inventory Control
Contractor Solution
Department Solution
Health Billing (ADP AADL)
Multi-Currency
Payroll
Secure Cloud Backup
Updates Included

11-20 Users

$139.00

per user, per month

Plan includes:

24/7 Live Customer Support
2-Factor Authentication
Add Ons – Advanced Inventory Control
Contractor Solution
Department Solution
Health Billing (ADP AADL)
Multi-Currency
Payroll
Secure Cloud Backup
Updates Included

21+ Users

$135.00

per user, per month

Plan includes:

24/7 Live Customer Support
2-Factor Authentication
Add Ons – Advanced Inventory Control
Contractor Solution
Department Solution
Health Billing (ADP AADL)
Multi-Currency
Payroll
Secure Cloud Backup
Updates Included

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Windward System Five Features

Popular features found in Retail Management Systems
Accounting Integration
CRM
eCommerce Management
Employee Management
Loyalty Program
Merchandise Management
Multi-Location
Order Management
Purchase Order Management
Reporting/Analytics
Retail Inventory Management
Returns Management
More features of Windward System Five
Access Controls/Permissions
Activity Dashboard
Age Verification
Alerts/Notifications
API
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
Electronic Signature
Email Marketing
Forecasting
For Liquor Stores
For Retail
Gift Card Management
Inspection Management
Inventory Management
Inventory Optimization
Inventory Replenishment
Inventory Tracking
Invoice Management
Item Management
Maintenance Management
Maintenance Scheduling
Multi-Channel Management
Multi-Currency
Ordering Automation
Payment Processing
Point of Sale (POS)
Price/Margin Management
Pricing Management
Product Catalog
Product Identification
Promotions Management
Quotes/Estimates
Real-Time Analytics
Real-Time Data
Real-Time Monitoring
Real-Time Reporting
Real-Time Updates
Receipt Management
Reporting & Statistics
Reservations Management
Retail 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

Windward System Five Integrations

Worldpay for Enterprise

Datacap

WooCommerce

Global Payments Integrated

WebSell

Windward System Five User Reviews

Overall Rating

3.8

Ratings Breakdown

37%

34%

11%

10%

Secondary Ratings

Ease of Use

3.7

Value for money

3.6

Customer support

3.7

Functionality

3.8

April T.

Verified reviewer

Consumer Services

11-50 employees

Used daily for more than 2 years

Reviewed June 2022

Windward review

Previously 4

Well built system that covers a lot of different types of business.

Ratings Breakdown

Ease of use

Previously 4

Value for money

Customer support

Functionality

Previously 4

Pros:

Unlimited features . Can do so much with a split business that we run.

Cons:

Would like to have more form creation options

Kathi M.

Verified reviewer

Retail

2-10 employees

Used daily for more than 2 years

Reviewed June 2024

We couldn't live with our our System 5

We couldn't do without them and their service is fantastic.

Ratings Breakdown

Ease of use

Value for money

Customer support

Functionality

Pros:

How the inventory management and purchasing work. So many extra features here that make it so helpful.

Cons:

How the form creation functions. It is a difficult process and way too time-consuming.

Reasons for choosing Windward System Five

We couldn't find any other software back in 2005 that would do order entry and point of sale all in one and hold as much inventory as we need. Windward was the only one at that time that was affordable.

Reasons for switching to Windward System Five

We had proprietary software written for out company. Our computer guy didn't want to support his program any longer. We used it in conjunction with Quick Books Pro.

Vendor Response

Thanks for your review! We're sure it will help a business owner make the right call by switching to Windward Software.

Replied September 2024

Trish H.

Retail

11-50 employees

Used daily for more than 2 years

Review source

Reviewed October 2017

Windward System 5 has made running our medium sized dealership much easier

Time and inventory management equals money savings

Ratings Breakdown

Ease of use

Previously 5

Value for money

Previously 5

Customer support

Functionality

Pros:

The point of sale system gives real time inventory tracking and the integrated accounting system saves hours of time each week

Cons:

The software is almost too in depth especially for users who are not computer savvy or who have a hard time learning new systems

Nava C.

Verified reviewer

Building Materials

2-10 employees

Used daily for more than 2 years

Review source

Reviewed July 2022

Great system management

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) WWS5 helps us keep track of items in inventory, current prices and mark-ups for inventory, general price increases from vendors, EOD reports and sales, and AR accounts much more easily. We do not currently use the accounting portion, but hope to move over to the accounting option with the new data set.

Ratings Breakdown

Ease of use

Value for money

Customer support

Functionality

Pros:

We currently use Windward for our POS and AR needs. This helps keep us on track for monthly billing to AR clients and keeps up with the daily till. We do very much like the additional features such as inventory management, price checks/updates, but have trouble at time keeping it current due to staffing issues. With more staff, this system would be absolutely amazing.

Cons:

When we first installed Windward, there were issues with understanding the larger picture during set-up. Understanding more about the system prior to set up would have helped. We are currently setting up a new database now that we understand more about the full operation of WWS5.

Reasons for choosing Windward System Five

Other POS options were too simplistic for our needs tracking hardwood lumber bought & sold by the board foot. WWS5 allows us to use the Z sheet to calculate board footage much more quickly when checking out customers and was not as expensive as other lumber yard systems.

Derek S.

Verified reviewer

Retail

11-50 employees

Used daily for more than 2 years

Reviewed June 2022

Windward Review

Mostly positive when it comes to day to day interaction. Any negatives are more nit-picking issues.

Ratings Breakdown

Ease of use

Value for money

Customer support

Functionality

Pros:

Required Orders system and ability to interact with the invoice easily throughout.

Cons:

Lack of multiple kits. Purchase orders with SO items become buggy with large quantities. If a user moves too quickly in the system, it can break.

Reasons for choosing Windward System Five

Price and size of the business did not warrant its need.

Reasons for switching to Windward System Five

Needed inventory management, the option for more departments

Jeff G.

Verified reviewer

Automotive

11-50 employees

Used daily for more than 2 years

Review source

Reviewed April 2024

FIX MOST ANY THING..FOR A COST

Ratings Breakdown

Ease of use

Value for money

Customer support

Functionality

Pros:

The system has many good functions and tracking abilities.

Cons:

Had to have a "wildcard" search for part numbers programmed in after they said it wasn't part of the system. It was already in the system for description but not for parts. As like so many other reviews, updates are a roll of the dice to see what will be affected when they are done. The biggest issue is, A PRICING MATRIX WITH VARIABLE RATES BASED ON COST. 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. That is $1.00 may be marked up 300% but $1000.00 isn't. That function does not exist and system 5 support team as well as account manager act as if I am the first person/business to want this incorporated into the system. I was told we could spend more money to have some one talk to us to tell us they don't know how to do this. The irony of it all is that I came from a Winworks System that we were out growing, but it had that function available to a great extent. Again kudos to the sales team for saying this system could do every thing we first questioned.

Reasons for switching to Windward System Five

Was promised Winward could do every thing we needed.

Vendor Response

Thanks for your feedback. We appreciate customer input like yours to help improve our software solutions and services. We are committed to fixing defects (bugs) that cause errors in our solutions at no extra charge for our customers. This has been our standard practice for over 40 years. We've assessed the complex pricing matrix you described in your feedback and understand that the requirements include varying percentages based on increasing cost tiers for parts. As you mentioned, this functionality does not exist in System Five and it is complex to build. Our Custom Development Services are designed to fulfill a request like this. We will build or enhance a solution to suit your unique needs. Yes, this type of custom work is a billable service. We encourage you to have a conversation with your Windward Account Manager for more information and to arrange for a consultation if this is important to your business. Our team is here to serve you and support your growth and success.

Replied May 2024

Bob N.

Verified reviewer

Furniture

2-10 employees

Used daily for less than 2 years

Reviewed June 2022

continuing forward

We are continuing to use System Five as migration is a challenge for a small business like ours. The support crew at Windward work well to address issues; however, our account manager failed to address items that were still in process just prior to go live. Those items remain outstanding as support is unable to address them.

Ratings Breakdown

Ease of use

Value for money

Customer support

Functionality

Pros:

Immediate processing of credit card transactions. The fact that System 5 is in the cloud is one of the primary reasons we purchased the product.

Cons:

Not enough explanation of defaults in System 5 caused redundancy in our chart of accounts. The monthly reconciliation requires that several routines be performed before you can have a reliable balance report of income/expense reports. Modifiers were disappointing as we learned that they must be setup on an item-by-item basis, rather than a category or brand basis. Custom reporting is extremely lacking and doesn't allow for us to produce the reports we need.

Reasons for choosing Windward System Five

The combination of financial and pos into a single application. The demos we went through for home furnishing solutions. Modifiers and their usage were also a primary reason we chose System 5. We found out after commitment that the modifiers would not work in our shop.

Reasons for switching to Windward System Five

The apps were on-prem based. We wanted a Cloud based solution. We thought the combination of a financial app and POS app would make things work smoother.

Rossie F.

Verified reviewer

Retail

2-10 employees

Used daily for more than 2 years

Reviewed June 2022

Windward Software is an amazing program to help you run your business in every aspect.

Inventory was a huge issue for us before we started using System Five. We absolutely cannot imagine running our business without Windward System Five at this point.

Ratings Breakdown

Ease of use

Value for money

Customer support

Functionality

Pros:

The Support is A1 and the features of everything from Inventory to Sales Invoices, everything is connected and very user friendly. Reports are easy to run, reconciliations, sales and purchase invoicing, ageing, financials are easy to read and all other functions are again, user friendly.

Cons:

No cons at this time. We didn't like that it didn't have a payroll feature when we started with it but now it does.

Reasons for choosing Windward System Five

When we were given a demonstration, we knew right away it could handle what we needed and more.

Reasons for switching to Windward System Five

We didn't like their Inventory feature or their GL postings that you could never correct even if it wasn't reconciled.

Shauna H.

Verified reviewer

Retail

11-50 employees

Used daily for more than 2 years

Reviewed November 2024

WindWard System 5 for Business

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.

Ratings Breakdown

Ease of use

Value for money

Customer support

Functionality

Pros:

It is a different system but once you get to know it and set it up for your business requirements it sets it apart from quickbooks and other accounting software. It is more POS friendly.

Cons:

The bugs that can happen where the system is not updating correctly. 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.

Mason B.

Verified reviewer

Consumer Goods

2-10 employees

Used monthly for less than 2 years

Review source

Reviewed August 2025

Slightly outdated, but intuitive and powerful

My overall experience was positive, and still is to some extent, though we largely use System Five as a database for older customer information now. Searching for historic records of customer purchases, inventory tracking over time, and loyalty program points still works very well.

Ratings Breakdown

Ease of use

Functionality

Pros:

Good value, and capabilities of software were far more advanced than I was expecting. Capable with inventory tracking, private customer data management, and invoicing.

Cons:

An outdated and clunky UI makes it much harder to utilize to its full capabilities, occasional long loading times, and annoying notifications about users connected to different pieces of hardware.

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