--- description: Detailed reviews on Windward System Five based on features, pricing, usability, and ratings. Get a quick overview advantages and disadvantages. Compare Windward System Five with similar products. image: https://gdm-localsites-assets-gfprod.imgix.net/images/getapp/og_logo-94fd2a03a6c7a0e54fc0c9e21a1c0ce9.png title: Windward System Five Reviews, Prices & Ratings | GetApp Canada 2026 --- Breadcrumb: [Home](/) > [Equipment Rental Software](/directory/1695/equipment-rental/software) > [Windward System Five](/software/126359/windward-system-five) # Windward System Five Canonical: https://www.getapp.ca/software/126359/windward-system-five Page: 1 / 9\ Next: [Next page](https://www.getapp.ca/software/126359/windward-system-five?page=2) > Integrated POS, inventory, CRM, and accounting software for growing businesses. Windward System Five supports complex workflows, KPI reporting with Windward Intelligence, and WebSell e‑commerce integration. > > Verdict: Rated **3.8/5** by 189 users. Top-rated for **Likelihood to recommend**. ----- ## Overview ### Key benefits of Windward System Five Operate from a single source of truth: Unify point of sale, inventory, CRM, and accounting in one platform to eliminate duplicate data, manual work, and disconnected systems. Handle complex operations with confidence: Support purchasing, receiving, multi‑location inventory, work orders, special orders, invoicing, and accounts receivable using configurable workflows that adapt to your business—not the other way around. Gain visibility with real business insights: Go beyond static reports with Windward Intelligence, an optional KPI dashboard that provides at‑a‑glance visibility into sales performance, margins, customer trends, and operational health. Simplify omnichannel selling: Integrate with WebSell to keep product and customer data synchronized across in‑store and online sales. Process web orders using the same fulfillment, invoicing, and accounting workflows as brick‑and‑mortar transactions. Flexible functionality with integrated add‑ons: Windward System Five offers a strong core platform with optional, internally developed add‑ons that extend functionality as your needs grow—so you can expand capabilities without relying on disconnected third‑party tools. Scale with personalized support: Get hands‑on onboarding, training, and ongoing support from a team that understands your industry and long‑term growth needs. ## Quick Stats & Ratings | Metric | Rating | Detail | | **Overall** | **3.8/5** | 189 Reviews | | Ease of Use | 3.7/5 | Based on overall reviews | | Customer Support Software | 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 Software - Availability Indicator - Availability Management - Barcode Recognition - Barcode/Ticket Scanning - Barcoding/RFID - Billing & Invoicing - CRM Software - 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 Software - Phone Support - 24/7 (Live rep) ## Category - [Equipment Rental Software](https://www.getapp.ca/directory/1695/equipment-rental/software) ## Related Categories - [Equipment Rental Software](https://www.getapp.ca/directory/1695/equipment-rental/software) - [Retail Management Systems Software](https://www.getapp.ca/directory/198/retail-management/software) - [Retail POS System Software](https://www.getapp.ca/directory/1603/retail-pos-system/software) - [Liquor Store POS Software](https://www.getapp.ca/directory/3447/liquor-store-pos/software) ## Alternatives 1. [Epos Now](https://www.getapp.ca/software/106871/epos-now) — 3.8/5 (716 reviews) 2. [RetailEdge](https://www.getapp.ca/software/128123/retailedge) — 4.8/5 (186 reviews) 3. [Shopify](https://www.getapp.ca/software/8275/shopify) — 4.5/5 (6686 reviews) 4. [PayPal](https://www.getapp.ca/software/91263/paypal) — 4.6/5 (26396 reviews) 5. [Lightspeed Retail](https://www.getapp.ca/software/91305/lightspeed-retail) — 4.0/5 (975 reviews) ## Reviews ### "Windward keeps us on track every day" — 4.0/5 > **Christine** | *January 28, 2021* | Retail | Recommendation rating: 9.0/10 > > **Pros**: It's easy to learn, use and does what we need it to ... and then some\! > > **Cons**: I'm sure we don't use all of the features to their full capability. The lack of a training manual is my only major concern. > > It's a great system and helps keep our inventory, estimates, sales and receipts organized ----- ### "We've been with Windward since 1994, recent years Windward has really stepped up to the plate \!\!" — 4.0/5 > **Kelly** | *November 13, 2017* | Furniture | Recommendation rating: 8.0/10 > > **Pros**: Over the years there have been many areas of the program that we never took advantage of. One of the greatest things is with all the recent available training on and off line it has allowed us to find these nuggets that have helped us tremendously to make processes within our business so much easier. This had to be one of the best implementations that Windward has made, keep the training coming\!\! > > **Cons**: The one thing we dislike about the program are updates. We get very nervous\! A few years ago we did an update and it totally messed up the whole program. We had to work offline (paper work) for more than 3 weeks, which was a nightmare after the fact. Though Windward programmers worked for over 6 months to find a fix, they never ever did. So here 5 or 6 years later our Point of Sales Transaction Report figures are still unusable. We recently updated Pervasive and were told it should really speed up the program. Unfortunately it didn't, actually saw absolutely no difference even though it had been several years since we'd done an update, so are looking at other areas now. > > One of the most recent benefits is the available training in many different areas of the Windward software program. This is an incredible asset to streamlining and improving day to day business practices for us. When we find out things the program can do for us that for years has just been sitting there not being used, we're like a kid in a candy shop....Excited...Wow\!\! ----- ### "Updated: By Far The Worst POS I've Ever Used (Support Included)" — 1.0/5 > **Kezia** | *November 9, 2020* | Retail | Recommendation rating: 0.0/10 > > **Pros**: In comparison to previous software used, the finalization of the inventory process within Windward is rather straight-forward. The ability to print count sheets with only product in stock - no part numbers with a "zero" quantity, is great and saves paper. However, products often randomly shift into categories like 'financial' which causes the item to remain on the inventory count. I have had to request help from support on this multiple times. > > **Cons**: I have used Windward software all day, every week day, for two years now and I consistently encounter issues in day to day operations. I have had problems with the cash out feature not allowing me to finalize the file and close the day; I am constantly getting error messages, or "unplanned shutdown" messages when an unplanned shutdown has not occurred; there are processing issues with rental invoices that cause the invoice totals to change, after the invoice has been finalized and submitted. This specifically has created MAJOR discrepancies on our invoices that has resulted in us to losing money, and having to issue apologies to many of our major accounts. One of these incidents has caused irreparable harm to our business relationship with our (previously) largest customer. > > I have been disappointed, and remain disappointed. I left a similar review a few months ago, and I was contacted by Windward in an effort to improve matters - which I do appreciate - but, unfortunately, that has not been enough to change my perspective on Windward. For myself, the general ease of use does not make up for the incredible amount of problems this software has. I have been working with various POS systems for over 10 years now, and this is the only one that ever inspired me to go out of my way and leave a review, because it's just so consistently problematic. I have been asked directly by the staff at Windward to update my review, and I do wish it had improved in any way, but I am more convinced than ever that there are much better choices out there. ----- ### "Lots of great features but maybe too many for a small business" — 4.0/5 > **Verified Reviewer** | *November 11, 2017* | Retail | Recommendation rating: 7.0/10 > > **Pros**: This program has a lot of features, many of which speed up the tasks we perform daily. Tracking our customers is now fairly easy. Most of the system is Excel compatible which makes invoices and other documents easy to export. Windward's tech support is very friendly and accommodating. > > **Cons**: As useful as this software is I still find simple tasks that it cannot perform. I have made at least four requests of tech support concerning software functionality that resulted in an answer of "the software can't do that" (and my requests were far from complicated). It's as if the software is so good at doing a million different tasks that it wasn't built to do the simplest ones. > > We can now track customer purchases more easily. Inventory control is faster and easier than before. ----- ### "Overall this software has a lot of capabilities that integrate easily into our company." — 4.0/5 > **Verified Reviewer** | *November 8, 2017* | Recommendation rating: 8.0/10 > > **Pros**: That it is easy to train our employees on. Great help videos\! I really like their integrated ecommerce. It is nice to update one price in our system and to have that price automatically updated on our website. > > **Cons**: Not so great for my outside sales staff. We run their WEAR program for our outside staff. It tends to have errors as it is similar to running just a backup version. I also wish that their ecommerce did not run in HTML only > > It saves me time. We used to run and inventory program, a bookkeeping program and an ecommerce program. It combined these 3 programs into one. ----- Page: 1 / 9\ Next: [Next page](https://www.getapp.ca/software/126359/windward-system-five?page=2) ## Links - [View on GetApp](https://www.getapp.ca/software/126359/windward-system-five) ## This page is available in the following languages | Locale | URL | | de | | | de-AT | | | en | | | en-AE | | | en-AU | | | en-CA | | | en-GB | | | en-IE | | | en-NZ | | | en-SG | | | en-ZA | | | es | | | es-CL | | | es-CO | | | es-MX | | | fr | | | fr-BE | | | fr-CA | | | nl | | | nl-BE | | ----- ## Structured Data