---
description: Compare Windward System Five vs Lightspeed Retail. Learn more about each of the software’s price, features, and helpful software reviews for Canadian business users.
image: https://gdm-localsites-assets-gfprod.imgix.net/images/capterra/og_logo-e5a8c001ed0bd1bb922639230fcea71a.png?auto=format%2Cenhance%2Ccompress
title: Windward System Five vs Lightspeed Retail Comparison - Capterra Canada 2026
---

Breadcrumb: [Home](/) > [Retail Management Systems Software](/directory/20053/retail-management-systems/software) > [Windward System Five \<span\>vs\</span\> Lightspeed Retail](https://www.capterra.ca/compare/43189/120491/windward-system-five/vs/lightspeed-retail)

# Compare Windward System Five vs Lightspeed Retail

Canonical: https://www.capterra.ca/compare/43189/120491/windward-system-five/vs/lightspeed-retail

> Detailed comparison between Windward System Five and Lightspeed Retail. Check ratings, reviews, pricing, and features to make the best decision for your business.

-----

## At a Glance

| Metric | Windward System Five | Lightspeed Retail |
| **Overall rating** | 3.8/5 | 4.0/5 |
| **Total Reviews** | 189 | 975 |
| **Starting Price** | US$155.00 | US$109.00 |
| **Free Trial** | Yes | Yes |
| **Free Version** | No | No |
| **Deployment** | Cloud, SaaS, Web-based, Windows (Desktop), Windows (On-Premise), Linux (On-Premise) | Cloud, SaaS, Web-based, Mac (Desktop), Windows (Desktop), Linux (Desktop), Chromebook (Desktop), iPad (Mobile) |
| **Support** | Email/Help Desk, FAQs/Forum, Knowledge Base Software, Phone Support, 24/7 (Live rep) | Email/Help Desk, FAQs/Forum, Knowledge Base Software, Phone Support, 24/7 (Live rep), Chat |
| **Training Software** | In Person, Live Online, Webinars, Documentation, Videos | Live Online, Webinars, Documentation, Videos |

## Best for

### Windward System Five

Independent SMBs in retail, wholesale, and service businesses needing a customizable POS + inventory + accounting suite with reporting and e‑commerce integration.

### Lightspeed Retail

Lightspeed's functionalities are aligned with retailers' and restaurateurs' priorities. It simplifies day-to-day tasks so you're free to focus on what matters: business growth and customer experience

## Key features

### Windward System Five

- API
- Billing & Invoicing
- Customer Database
- Customizable Reports
- Discount Management
- Inventory Management Software
- Inventory Replenishment
- Merchandise Management
- Ordering Automation
- Point of Sale (POS)
- Pricing Management
- Product Catalog
- Real-Time Analytics
- Real-Time Data
- Real-Time Reporting
- Retail Inventory Management Software
- Returns Management
- Stock Management
- Supplier Management
- eCommerce Management

### Lightspeed Retail

- API
- Billing & Invoicing
- Customer Database
- Customizable Reports
- Discount Management
- Inventory Management Software
- Inventory Replenishment
- Merchandise Management
- Ordering Automation
- Point of Sale (POS)
- Pricing Management
- Product Catalog
- Real-Time Analytics
- Real-Time Data
- Real-Time Reporting
- Retail Inventory Management Software
- Returns Management
- Stock Management
- Supplier Management
- eCommerce Management

## Links

- [View Windward System Five Profile](https://www.capterra.ca/software/43189/windward-system-five)
- [View Lightspeed Retail Profile](https://www.capterra.ca/software/120491/lightspeed-retail)
- [View Original Comparison](https://www.capterra.ca/compare/43189/120491/windward-system-five/vs/lightspeed-retail)

-----

## Structured Data

<script type="application/ld+json">
  {"@context":"https://schema.org","@graph":[{"name":"Windward System Five vs Lightspeed Retail Comparison - Capterra Canada 2026","description":"Compare Windward System Five vs Lightspeed Retail. Learn more about each of the software’s price, features, and helpful software reviews for Canadian business users.","url":"https://www.capterra.ca/compare/43189/120491/windward-system-five/vs/lightspeed-retail","about":[{"@id":"https://www.capterra.ca/software/43189/windward-system-five#software"},{"@id":"https://www.capterra.ca/software/120491/lightspeed-retail#software"}],"breadcrumb":{"@id":"https://www.capterra.ca/compare/43189/120491/windward-system-five/vs/lightspeed-retail#breadcrumblist"},"@type":["WebPage","CollectionPage"],"@id":"https://www.capterra.ca/compare/43189/120491/windward-system-five/vs/lightspeed-retail#webpage","publisher":{"@id":"https://www.capterra.ca/#organization"},"inLanguage":"en-CA","isPartOf":{"@id":"https://www.capterra.ca/#website"}},{"name":"Windward System Five","description":"Windward System Five is an all‑in‑one business management platform that brings point of sale, inventory control, CRM, and accounting into one system. \nRun purchasing and receiving, manage work/special orders, fulfill and invoice customers, and track accounts receivable—so your team can operate from one source of truth. \nBuilt‑in reporting is extended with Windward Intelligence, a KPI dashboard that helps you monitor sales, margins, customers, and more. \nFor omnichannel selling, connect System Five to WebSell to sync products and customers and handle web orders using the same workflows as in‑store. \nHighly configurable to fit complex operations, backed by personalized support and training.","image":"https://gdm-catalog-fmapi-prod.imgix.net/ProductScreenshot/4879d4b8-c7bd-45f8-94ec-72b4c6f239f7.png","url":"https://www.capterra.ca/software/43189/windward-system-five","@type":"SoftwareApplication","@id":"https://www.capterra.ca/software/43189/windward-system-five#software","applicationCategory":"BusinessApplication","publisher":{"@id":"https://www.capterra.ca/#organization"},"aggregateRating":{"@type":"AggregateRating","bestRating":5,"ratingCount":189,"ratingValue":3.8},"offers":{"price":"155","@type":"Offer","priceCurrency":"USD"},"operatingSystem":"Cloud, Windows, Windows on premise, Linux on premise"},{"name":"Lightspeed Retail","description":"This POS platform makes retail easier for everyone. Whether you’re just getting started or building your empire, Lightspeed’s got you covered. Simplify inventory management with a sophistacted product catalog that unites all your locations from a single dashboard. \n\n- Manage Inventory faster\n- Get Lightspeed's Hardware\n- Create exceptional customer experiences\n- Keep an eye on performance in over 40 built-in reports\n- Lightspeed Payments","image":"https://gdm-catalog-fmapi-prod.imgix.net/ProductScreenshot/a6b10944-e870-485c-b999-c1353bacf590.png","url":"https://www.capterra.ca/software/120491/lightspeed-retail","@type":"SoftwareApplication","@id":"https://www.capterra.ca/software/120491/lightspeed-retail#software","applicationCategory":"BusinessApplication","publisher":{"@id":"https://www.capterra.ca/#organization"},"aggregateRating":{"@type":"AggregateRating","bestRating":5,"ratingCount":975,"ratingValue":4.0},"offers":{"price":"109","@type":"Offer","priceCurrency":"USD"},"operatingSystem":"Cloud, Apple, Windows, Linux, Chrome, Platform ipad"},{"@type":"BreadcrumbList","itemListElement":[{"name":"Home","position":1,"item":"/","@type":"ListItem"},{"name":"Retail Management Systems Software","position":2,"item":"/directory/20053/retail-management-systems/software","@type":"ListItem"},{"name":"Windward System Five vs Lightspeed Retail","position":3,"item":"https://www.capterra.ca/compare/43189/120491/windward-system-five/vs/lightspeed-retail","@type":"ListItem"}],"@id":"https://www.capterra.ca/compare/43189/120491/windward-system-five/vs/lightspeed-retail#breadcrumblist"}]}
</script>