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Windward System Five

Cloud-based business management solution | ERP for your SMB

Table of Contents

Is this product right for your business?

Find out with a

Windward System Five - 2026 Pricing, Features, Reviews & Alternatives

All user reviews are verified by in-house moderators and provider data by our software research team. Learn more

Last updated: March 2026

Windward System Five overview

What is Windward System Five?

Windward System Five is a fully integrated business management platform designed for independent and growing businesses with complex operational needs. It combines point of sale (POS), inventory management, CRM, and accounting into a single system, providing a consistent and accurate data foundation across the organization.

System Five supports end‑to‑end operational workflows, including purchasing and receiving, multi‑location inventory management, work orders and special orders, invoicing, and accounts receivable. The platform is highly configurable, allowing businesses to adapt pricing, inventory structures, workflows, and permissions to match real‑world operations rather than forcing process changes to fit the software.

Native reporting is extended through Windward Intelligence, an optional analytics layer that delivers KPI dashboards and performance visibility across sales, margins, customers, and operational trends. This enables managers and owners to move beyond static reports and monitor business health in near real time.

For businesses selling both in‑store and online, Windward System Five integrates with WebSell for e‑commerce. Product, pricing, and customer data remain synchronized, and online orders are processed using the same fulfillment, invoicing, and accounting workflows as brick‑and‑mortar transactions—simplifying omnichannel operations and reducing manual work.

Windward System Five is supported by personalized onboarding, training, and ongoing support, making it a strong fit for organizations that value flexibility, long‑term scalability, and direct access to knowledgeable product experts.

Starting price

135per user /
per month

Alternatives

with better value for money

Pros & Cons

Reporting

Training and Learning Curve

Sales Reporting

Customer Support

Customization

Frequent software errors and glitches

Windward System Five’s user interface

Ease of use rating:

3.8

(189)

Windward System Five pros, cons and reviews insights

To determine these pros and cons insights, we analyzed responses from

Overall rating

Reviews sentiment

1-2(34)

3-4(84)

5(71)

What do users say about Windward System Five?

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

Select to learn more

Who uses Windward System Five?

Based on 189 verified user reviews.

Company size

Small Businesses

Midsize Businesses

Enterprises

Top industries

Retail

Consumer Goods

Automotive

Furniture

Others

Use cases

Retail POS System

Retail Management Systems

Windward System Five's key features

Most critical features, based on insights from Windward System Five users:

Returns management

3.0

(2)

Retail inventory management

3.7

(10)

Reporting/Analytics

2.7

(6)

Purchase order management

3.3

(7)

Order management

3.7

(15)

Multi-Location

3.0

(8)

CRM

2.5

(2)

eCommerce management

3.0

(11)

Merchandise management

3.0

(1)

Accounting integration

(0)

All Windward System Five features

Features rating:

3.8

(189)

Access controls/permissions

(0)

Accounting integration

(0)

Activity dashboard

(0)

Age verification

(0)

Alerts/Notifications

(0)

API

(0)

Asset lifecycle management

(0)

Asset tracking

(0)

Availability indicator

(0)

Availability management

(0)

Barcode recognition

(0)

Barcode/Ticket scanning

5.0

(1)

Barcoding/RFID

(0)

Billing & invoicing

3.5

(4)

Calendar management

(0)

Cash management

(0)

Commission management

(0)

Contract/License management

4.0

(1)

Cost tracking

3.9

(19)

Credit card processing

(0)

CRM

2.5

(2)

Customer accounts

(0)

Customer database

(0)

Customer history

(0)

Customer management

(0)

Customizable reports

(0)

Data import/export

5.0

(1)

Data synchronization

(0)

Discount management

3.8

(5)

Document management

(0)

Document storage

(0)

eCommerce management

3.0

(11)

Electronic signature

(0)

Email marketing

(0)

Employee management

(0)

Forecasting

3.0

(4)

For liquor stores

(0)

For retail

3.4

(16)

Gift card management

(0)

Inspection management

(0)

Inventory management

3.9

(23)

Inventory optimization

5.0

(1)

Inventory replenishment

(0)

Inventory tracking

(0)

Invoice management

(0)

Item management

(0)

Loyalty program

(0)

Maintenance management

(0)

Maintenance scheduling

(0)

Merchandise management

3.0

(1)

Multi-Channel management

(0)

Multi-Currency

(0)

Multi-Location

3.0

(8)

Ordering automation

5.0

(1)

Order management

3.7

(15)

Payment processing

3.0

(2)

Point of sale (pos)

3.8

(25)

Price/Margin management

(0)

Pricing management

4.0

(5)

Product catalog

(0)

Product identification

4.1

(14)

Promotions management

(0)

Purchase order management

3.3

(7)

Quotes/Estimates

(0)

Real-Time analytics

(0)

Real-Time data

(0)

Real-Time monitoring

(0)

Real-Time reporting

(0)

Real-Time updates

(0)

Receipt management

(0)

Reporting/Analytics

2.7

(6)

Reporting & statistics

(0)

Reservations management

3.3

(3)

Retail inventory management

3.7

(10)

Retail management

4.3

(6)

Returns management

3.0

(2)

Returns tracking

(0)

Sales order management

(0)

Sales reports

4.2

(25)

Sales tax management

(0)

Sales trend analysis

(0)

Scheduling

(0)

Search/Filter

(0)

Shipping management

(0)

Stock management

(0)

Supplier management

(0)

Third-Party integrations

(0)

Touch screen

(0)

Transaction history

(0)

Utilization reporting

(0)

Warehouse management

(0)

Work order management

(0)

Windward System Five alternatives

Windward System Five

3.8

(189)

Starting from

135

/user

Per month

Free trial

Free version

Ease of Use

3.7

Features

3.8

Value for Money

3.6

Customer Support

3.8

Epos Now

3.8

(715)

learn more

Starting from

349

One-time payment

Free trial

Free version

Ease of Use

3.8

Features

3.8

Value for Money

3.6

Customer Support

3.6

Shopify

4.5

(6.6K)

learn more

Starting from

Per month

Free trial

Free version

Ease of Use

4.5

Features

4.4

Value for Money

4.3

Customer Support

4.4

RetailEdge

4.8

(186)

learn more

Starting from

495

One-time payment

Free trial

Free version

Ease of Use

4.7

Features

4.6

Value for Money

4.8

Customer Support

4.8

Windward System Five pricing

Value for money rating:

3.6

Pricing plans

Pricing details:

Free plan

Free trial

Subscription

2-10 Users

155

/user

Per month

Features included:

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
Windward Intelligence
Windward SCAN App

11-20 Users

139

/user

Per month

Features included:

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
Windward Intelligence
Windward SCAN App

21+ Users

135

/user

Per month

Features included:

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
Windward Intelligence
Windward SCAN App

User opinions about Windward System Five price and value

Value for money rating:

3.6

(189)

To see what individual users think of Windward System Five's price and value, check out the review snippets below.

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

Mason B.

Sales Associate

“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.)”

Greg H.

Owner

Windward System Five integrations (5)

Integrations rated by users

We looked at 189 user reviews to identify which products are mentioned as Windward System Five integrations and how users feel about them.

Worldpay for Enterprise

Integration rating: 4.0 (2)

“Payment Processor for credit card payments.”

Sal W.

Director Of Operations

WooCommerce

Integration rating: 1.0 (1)

“Customers and administrators alike expect prompt notifications and Mailgun does that at a fraction of the cost of their competitors. I wish all our eCommerce clients would use Mailgun!”

“Turn any site into a shop in minutes”

Benjamin W.

Lead Engineer and General Manager

1/2