---
description: Review of Windward System Five Software: system overview, features, price and cost information. Get free demos and compare to similar programs on Software Advice New Zealand.
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title: Windward System Five | Reviews, Pricing & Demos - SoftwareAdvice NZ
---

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# Windward System Five

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> 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 System Five is backed by personalized onboarding, training, and ongoing support, helping businesses implement confidently and scale at their own pace.
> 
> Verdict: Rated **3.8/5** by 189 users. Top-rated for **Likelihood to recommend**.

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## Quick Stats & Ratings

| Metric | Rating | Detail |
| **Overall** | **3.8/5** | 189 Reviews |
| Ease of Use | 3.7/5 | Based on overall reviews |
| Customer Support | 3.7/5 | Based on overall reviews |
| Value for Money | 3.6/5 | Based on overall reviews |
| Features | 3.8/5 | Based on overall reviews |
| Recommendation percentage | 70% | (7/10 Likelihood to recommend) |

## About the vendor

- **Company**: Windward Software
- **Location**: Penticton, Canada
- **Founded**: 1984

## Commercial Context

- **Starting Price**: US$155.00
- **Pricing model**: Per User (Free Trial)
- **Pricing Details**: Pricing plans range from $131 to $150\* per user per month, plus a one-time implementation fee.
\*based on user count.
Note: Windward Software typically bills yearly, monthly rates are for comparative purposes. Talk to your rep for options.
- **Target Audience**: Self Employed, 2–10, 11–50, 51–200
- **Deployment & Platforms**: Cloud, SaaS, Web-based, Windows (Desktop), Windows (On-Premise), Linux (On-Premise)
- **Supported Languages**: English
- **Available Countries**: Australia, Canada, United States

## Features

- API
- 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
- CRM
- Calendar Management
- Cash Management
- Commission Management
- Contract/License Management
- Cost Tracking

## Integrations (6 total)

- Datacap
- Global Payments Integrated
- Polaris
- WebSell
- WooCommerce
- Worldpay for Enterprise

## Support Options

- Email/Help Desk
- FAQs/Forum
- Knowledge Base
- Phone Support
- 24/7 (Live rep)

## Category

- [Retail Management Software](https://www.softwareadvice.co.nz/directory/2025/retail-management/software)

## Related Categories

- [Retail Management Software](https://www.softwareadvice.co.nz/directory/2025/retail-management/software)
- [Retail Accounting Software](https://www.softwareadvice.co.nz/directory/31/accounting-software/software)
- [Liquor Store POS Software](https://www.softwareadvice.co.nz/directory/84/liquor-store-software/software)
- [Sporting Goods POS Software](https://www.softwareadvice.co.nz/directory/109/sporting-goods-store-software/software)
- [Furniture Store Software](https://www.softwareadvice.co.nz/directory/37/furniture-store-retail-software/software)

## Alternatives

1. [Epos Now](https://www.softwareadvice.co.nz/software/21000/epos-now) — 3.8/5 (713 reviews)
2. [Clover](https://www.softwareadvice.co.nz/software/61761/clover) — 3.8/5 (567 reviews)
3. [Shopify](https://www.softwareadvice.co.nz/software/390630/shopify) — 4.5/5 (6667 reviews)
4. [RetailEdge](https://www.softwareadvice.co.nz/software/1162/retailedge) — 4.8/5 (186 reviews)
5. [PayPal](https://www.softwareadvice.co.nz/software/104664/paypal) — 4.6/5 (26301 reviews)

## Reviews

### "Windward review" — 5.0/5

> **April** | *21 June 2022* | Consumer Services | Recommendation rating: 10.0/10
> 
> **Pros**: Unlimited features .  Can do so much with a split business that we run.
> 
> **Cons**: Would like to have more form creation options
> 
> Well built system that covers a lot of different types of business.

-----

### "We couldn't live with our our System 5" — 5.0/5

> **Kathi** | *6 June 2024* | Retail | Recommendation rating: 9.0/10
> 
> **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.
> 
> We couldn't do without them and their service is fantastic.

-----

### "Windward System 5 has made running our medium sized dealership much easier" — 5.0/5

> **Trish** | *25 October 2017* | Retail | Recommendation rating: 10.0/10
> 
> **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
> 
> Time and inventory management equals money savings

-----

### "Great system management" — 5.0/5

> **Nava** | *6 July 2022* | Building Materials | Recommendation rating: 8.0/10
> 
> **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.
> 
> 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.

-----

### "Windward Review" — 4.0/5

> **Derek** | *20 June 2022* | Retail | Recommendation rating: 7.0/10
> 
> **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.
> 
> Mostly positive when it comes to day to day interaction. Any negatives are more nit-picking issues.

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## Links

- [View on SoftwareAdvice](https://www.softwareadvice.co.nz/software/161668/windward-system-five)

## This page is available in the following languages

| Locale | URL |
| en | <https://www.softwareadvice.com/retail/windward-system-five-profile/> |
| en-AU | <https://www.softwareadvice.com.au/software/161668/windward-system-five> |
| en-GB | <https://www.softwareadvice.co.uk/software/161668/windward-system-five> |
| en-IE | <https://www.softwareadvice.ie/software/161668/windward-system-five> |
| en-NZ | <https://www.softwareadvice.co.nz/software/161668/windward-system-five> |

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