# Compare Windward System Five vs Square for Retail 2026 | Capterra > Unsure of what to choose? Check Capterra to compare Windward System Five and Square for Retail based on pricing, features, product details, and verified reviews. Source: https://www.capterra.com/compare/43189-170272/Windward-System-Five-vs-Square-for-Retail --- # Windward System Five vs Square for Retail Features and Cost Comparison Last updated June 14th, 2026 Provider data verified by our Software Research team, and reviews moderated by our Reviews Verification team.[Learn more](https://www.capterra.com/our-story/) Your comparison: Windward System FiveSquare for Retail2/4 selected [Windward System Five](https://www.capterra.com/p/43189/Windward-System-Five/)[3.8 (189)](https://www.capterra.com/p/43189/Windward-System-Five/reviews/) [Square for Retail](https://www.capterra.com/p/170272/Square-for-Retail/)[4.7 (493)](https://www.capterra.com/p/170272/Square-for-Retail/reviews/) [## Windward System Five](https://www.capterra.com/p/43189/Windward-System-Five/)[3.8 (189)](https://www.capterra.com/p/43189/Windward-System-Five/reviews/) Starting Price $135.00/month Value-for-Money 3.6 Functionality 3.8 Ease of Use 3.7 Customer Service 3.7 Reviews Sentiment MB JG Based on [189 reviews](#user-reviews) Positive 135 Neutral 20 Negative 34 [## Square for Retail](https://www.capterra.com/p/170272/Square-for-Retail/)[4.7 (493)](https://www.capterra.com/p/170272/Square-for-Retail/reviews/) Starting Price Contact vendor Value-for-Money 4.5 Functionality 4.5 Ease of Use 4.7 Customer Service 4.3 Reviews Sentiment Based on [493 reviews](#user-reviews) Positive 469 Neutral 13 Negative 11 ## Send this comparison chart to my inbox ### Fill out the form and we'll send a list of the top-rated software based on real user reviews directly to your inbox. What’s your intended use case? ## Summary * * * Key features rated by users Features selected based on 2,710 reviews from retail pos system software users. about the Fit Score methodology. Fit Score methodology Our Fit Score reflects how reviewers rate a product’s performance against a set of features reviewers rate as most important. A higher score indicates the product is rated better in delivering what reviewers most care about. If the Fit Score is not shown for a specific product, that only means there are currently not enough relevant data points to develop a meaningful score. It does not indicate that the product should be excluded from further evaluation. Best for Methodology 70%Fit Feature ratings For Retail 3.4 Payment Processing 3.0 Inventory Management 3.9 Sales Reports 4.2 eCommerce Management 3.0 81%Fit High performer Feature ratings For Retail 4.6 Payment Processing 4.6 Inventory Management 4.4 Sales Reports 4.6 eCommerce Management 4.5 User satisfaction User satisfaction 3.8 User reviews[189](https://www.capterra.com/p/43189/Windward-System-Five/reviews/) Ease of use 3.7 Functionality 3.8 Value for money 3.6 Customer support 3.7 User satisfaction 4.7 User reviews[493](https://www.capterra.com/p/170272/Square-for-Retail/reviews/) Ease of use 4.7 Functionality 4.5 Value for money 4.5 Customer support 4.3 Price starts from Price starts from $135Per User, Per Month - Free version - Free trial Price starts from \-- - Free version - Free trial Best for Best for Independent retailers, wholesalers, and service businesses replacing disconnected apps with one configurable platform for POS, inventory, CRM, accounting, and real-time reporting. Best for Whether you sell online or in store, Square for Retail can work for your retail business no matter your size or style. ## User reviews Pros & cons MB Mason B. Sales Associate > "Searching for historic records of customer purchases, inventory tracking over time, and loyalty program points still..." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___6867392) MB Mason B. Sales Associate > "An outdated and clunky UI makes it much harder to utilize to its full capabilities, occasional long loading times, and..." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___6867392) JG Jeff G. PARTS MANAGER > "The system has many good functions and tracking abilities." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#SoftwareAdvice___6280649) GH Greg H. Owner > "It would appear that no one at Windward has EVER used the software for any length of time because bugs and usability..." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___6837346) NC Nava C. Owner > "WWS5 helps us keep track of items in inventory, current prices and mark-ups for inventory, general price increases..." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3620314) SH Shauna H. Accounts Payable Manager and Bookkeeping Assistant > "The bugs that can happen where the system is not updating correctly." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___6579201) KM Kathi M. CEO > "We couldn't do without them and their service is fantastic. " [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___6333636) JG Jeff G. PARTS MANAGER > "That function does not exist and system 5 support team as well as account manager act as if I am the first..." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#SoftwareAdvice___6280649) RF Rossie F. Owner > "The Support is A1 and the features of everything from Inventory to Sales Invoices, everything is connected and very..." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3589555) AU Anatoly U. owner > "spent alot of resources and time to get their web module to sell online and they discontinued it the next year just as..." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___5006523) JS Justin S. President > "The integrated CRM is very useful for keeping track of appointments and follow ups." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3477329) GH Greg H. Owner > "Exporting our data is a nightmare." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___6837346) RF Rossie F. Owner > "Reports are easy to run, reconciliations, sales and purchase invoicing, ageing, financials are easy to read and all..." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3589555) GH Greg H. Owner > "From one of System 5's oldest customers - stay out of this swamp!" [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___6837346) GF Grant F. IT Manager > "They worked with me in implementing and transferring our data with only a few hickups." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3611104) GH Greg H. Owner > "Please please please save yourself - DO NOT buy into this software." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___6837346) HA Heather A. owner > "When we first started with windward it was fantastic. If we needed support, we called in Australia and it was fixed...." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3589775) CN Christine N. Controller > "The control numbers should change what is in the je. When I addressed the issue, I was brushed off and just told to..." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3603641) JR Jordan R. Sales Associate > "Plenty of automated systems, the required orders feature is nice." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3591398) DM Derek M. V.P. > "Service and online capability was not good. While we paid for 24/7 service, we had to setup tickets and would get a..." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3591330) JG Jody G. general manager > "We have invested heavily in to the software on the years and would.lien to feel we can get value added serviced..." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3589707) BN Bob N. Co-Owner > "The support crew at Windward work well to address issues; however, our account manager failed to address items that..." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3599240) BN Bob N. Co-Owner > "The fact that System 5 is in the cloud is one of the primary reasons we purchased the product." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3599240) AF Adirna F. Accounting Manager > "It can take them up to 2 weeks to get critical fixes completed or for you do discuss with a developer because tech..." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3619722) HS Heidi S. Accounts Payable > "POS is easy to use and we also use it for some accounting and for work orders/purchase orders." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3589695) NL Nannette L. owner > "Having to buy hours for pricing updates and having them expire before all our vendors print their new pricing." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3591532) MD Madison D. PURCHASER > "The reports have vast options which we utilize often." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3603502) SB Stephine B. Office Manager/ Owner > "Have not figured out how to use the special order part and see if we are ordering a lot of one part and therefore..." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3618125) FH Frank H. President > "I like the reporting ability and the integration across all departments, jobs and overall robust accounting ability" [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___2679839) BN Bob N. Co-Owner > "Not enough explanation of defaults in System 5 caused redundancy in our chart of accounts." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3599240) TY TODD Y. manager/it > "Integration between order taking and purchasing has helped speed up the ordering process & stop mistakes being made. " [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___2684601) AF Adirna F. Accounting Manager > "Running reports has become cumbersome as you have to run on their remote desktop and copy to your own." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3619722) EH Edith H. Owner/operator > "It has saved me about $2000.00/year in accountant fees. " [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3625158) LS Lori S. Buyer > "Handling back orders arent great as well as a few glitches that are waiting to be fixed." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3591308) BK Bilal K. General Manager > "Windward Software's system allows us to stay on track and be able to organize vital information." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___2727138) RF Rossie F. Owner > "We didn't like that it didn't have a payroll feature when we started with it but now it does." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3589555) LL Larry L. Purchaser > "The product also includes a rental component which is also fairly simple to operate." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3603750) NC Nava C. Owner > "When we first installed Windward, there were issues with understanding the larger picture during set-up. " [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3620314) EH Edith H. Owner/operator > "So easy to upload inventory that is new from an excel spreadsheet." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3625158) CN Christine N. Controller > "Having trouble intigrating Windward System Five, with shipping programs." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3603641) ET Eva T. Controller > "Over the years there was a lot of frustration with support but it has been getting better and quicker" [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3619918) SB Stevenson B. director > "The payroll reports (designing) are difficult to understand" [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3591369) EH Edith H. Owner/operator > "A new employee who had experience with other systems encouraged me to purchase." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3625158) TY TODD Y. manager/it > "That was done, but they didnt change non-stock special orders where you have to manually type in the characters. ..." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___2684601) LL Larry L. Purchaser > "Ease of use, Windows familiarity help to make a decent experience." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3603750) AF Adirna F. Accounting Manager > "We have had issues with inventory which is a critical part of our business. " [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3619722) KK Kezia K. Sales/Reception > "In comparison to previous software used, the finalization of the inventory process within Windward is rather..." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___2498467) RF Rossie F. Owner > "Inventory was a huge issue for us before we started using System Five. " [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3589555) EW Ed W. Partner > "We needed a lot of hand holding when we first started--I had no previous experience with POS software--and Windward..." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___2649278) MD Madison D. PURCHASER > "There is not one week we do not have issues in our system, user or system error." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3603502) FH Frank H. President > "Overall, this has been a great money saving tool. But the shortcomings in the software probably has more to do with..." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___2679839) HS Hyacinte S. Bookkeeper > "A lot of times when there are issues it is not easy to find the help in your help section." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3591685) BK Bilal K. General Manager > "Nationwide Furniture Mattress Outlet looks forward to continuing and growing our partnership with Windward Software." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___2727138) ZW Zoe W. Owner > "Windaward technicians use a licence you have paid for to investigate their system's issues further undermining your..." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#SoftwareAdvice___2510835) JS Justin S. President > "I am very happy I made this investment" [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3477329) JS Justin S. President > "Booking orders use to take me days to put together." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3477329) LJ Laura J. Corporate Secretary/Business Manager > "Seemed easy to set up." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#SoftwareAdvice___3448158) EW Ed W. Partner > "That feature no longer works for us in the cloud, and I'm told that the reason why is that the cloud version of..." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___2649278) SB Stephine B. Office Manager/ Owner > "Easy to use and teach employees." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3618125) DS Derek S. Manager > "Lack of multiple kits." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3589561) JM Julie M. Controller > "We were able to import with very little mistakes." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___2684410) BA Bob A. CFO > "Upgrades are hard to keep updated again ,the users fault." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3591594) EW Ed W. Partner > "Another thing I like about Windward is the quality of Windward's support. " [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___2649278) MD Madison D. PURCHASER > "We always seem to be chasing down issues and fixing bugs." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3603502) LH Larry H. CFO and Owner > "The cloud-based system is easy to access and use on a daily basis." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___2651670) VV Victoria V. Accounts Receiable > "Some of the reporting features make getting an accurate snapshot of what is occurring in the company a little difficult" [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___2649123) JM Julie M. Controller > "Setting up a new customer is very easy." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___2684410) GF Grant F. IT Manager > "Not as customizable as I would like." [See full review](https://www.capterra.com/p/43189/Windward-System-Five/#Capterra___3611104) [View Reviews](https://www.capterra.com/p/43189/Windward-System-Five/reviews/) JP Jabbara P. Owner > "It's a very simple payment processing service... with a few bells and whistles." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___7163939) Amie O. Point of Sale Inventory Control manager > "We had a transient business and the sales tax programming was a bit cumbersome, having to change them weekly..." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___6872576) JP Jabbara P. Owner > "It's helped me over the years to keep track of items/stock." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___7163939) AS Amy S. Owner > "I operated in good faith, with no chargebacks or history of fraud, and now my ability to serve customers and..." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#SoftwareAdvice___7042305) AC Alisa C. Owner > "I have complete control over each transaction and can run any sales or promotions that I want!" [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___6599340) DK Demi K. Owner > "Sometimes based on your internet, it can be a pain to work with." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___6128789) AR Anthony R. Web Developer > "The system is straightforward, fast to learn, and reliable for day‑to‑day retail operations." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___7064934) RF Rose F. owner > "We constantly count and fix the inventory numbers in the system and within days they're wrong again." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#SoftwareAdvice___3872944) SG Steve G. Owner > "It makes it very easy to use for a fast paced retail environment and it has lots of options to help add..." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___6588991) VR Verified Reviewer Marketing Manager > "I did not enjoy order issues and payment issues on the square software." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___4409451) Kurt Z. Owner > "Square is very easy to set up and very user friendly when in use." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___7075107) RC Renee C. HR Rep > "Connectivity issues with WIFI occasionally" [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___4586055) CM Caitlyn M. Buyer > "My overall experience was okay, there’s are more pros than cons, but the cons hold more value than the pros." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___7068343) NH Nathan H. Owner/chiropractor > "Occasionally have difficulty getting software to connect with internet to process cards and the..." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___2958609) MP Michal P. Software Engineer > "There is a lot of documentation that can be accessed." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___6805046) CB Carrie B. NutriStore Supervisor > "I called square to ask about being locked out of my account and the customer service rep (\[SENSITIVE..." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___4225431) MH Mitchell H. Senior Consultant > "It is easy to use, easy to create an account, and simple to add inventory with pictures and descriptions!" [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___6602752) AR Angel R. Nail Tech > "It is a bit expensive for the limited features you get." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___4503168) AS Amy S. Owner > "At first it was easy. " [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#SoftwareAdvice___7042305) KI Kate I. Chiropractor > "Nothing - this was quick - sometimes connection was challenging if internet was poor." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___4097409) AL Angela L. Owner > "It builds instant credibilty with the consumer." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___5038290) AR Angel R. Nail Tech > "The app crashes a lot as well." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___4503168) LNR Laly Noya R. CEO > "Also, my customers are able to purchase without any hassle." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___6048238) RF Rose F. owner > "My inventory numbers are always wrong." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#SoftwareAdvice___3872944) GD Grace D. Advocate > "I am not a huge business but it's great to have access to a more robust feature set which I think is what..." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___4233418) MA Melanie A. Business Owner > "I had to sit with my bank to file a dispute with Square, put a hold on all charges by Square, and start..." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___2856217) HH Heather H. Order Management III > "This seems like the best program for small businesses." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___5023492) TW Travis W. Operations Manager > "The void system being only for restaurant usage is a bit frustrating. " [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___2962174) RC Renee C. HR Rep > "Overall, Square has simplified our POS system and with its easy to use reporting, we are able to manage our..." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___4586055) KH Kelsey H. lot manager > "Really really challenging to use on a ipad for scheduling and adjusting people's time cards." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___3322087) ST Savannah T. CFO > "We're able to set it up on the go and really able to make our customers feel comfortable giving us their..." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___2985110) CV Crayle V. Freelancer > "It just kept sending bursts of 3-5 messages with links to broken pages on their website based on key words..." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___2911045) MM Michael M. Owner > "Processing payments and a payout at the end of the day makes retail a breeze." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___4720076) DB Daniel B. VP > "I wish we had never contacted this bad company. If you choose them be AWARE at your own risk they might hold..." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#GetApp___3021593) KI Kate I. Chiropractor > "Square for retail is a great option for small business looking for a POS system to implement quickly." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___4097409) DB Daniel B. VP > "Square has terrible customer service and poor crisis management." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#GetApp___3021593) LB Laura B. First Impressions Director > "We have rotated stock, added new and taken out old, and updating the system has been very clear and easy." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___3731257) ER Edgar R. Endpoint Technician > "Coincidentally, the party I was conducting business with was a tax-exempt business and I had no idea how to..." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___3298077) CR Connor R. IT Support > "this product is a small business dream and makes transactions seamless" [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___4285077) AR April R. Owner > "The fees are so high." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___3642072) RH REBECCA H. WARRANTY CLERK > "EASY AND USER FRIENDLY, SIMPLE TO DO NIGHTLY ACCOUNTING" [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___6144122) EU Ela U. Owner > "the app works only on ios and not available on android" [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___3582604) LK Lynn K. Pastor > "Cost and set up were both affordable and easy, plus transactions were never an issue on any device or credit..." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___4146912) TD Tara D. Merchandiser > "the high percentage to do a transaction is only thing I don't like" [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___3472982) GD Gemma D. Admin > "The small size and ease of use of the square reader makes processing our transactions as easy as possible!" [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___3776217) DE Daniel E. Senior Pastor > "However, for the scanner to work, the terminal must be plugged into an outlet, which robs it of its portable..." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___2825375) John A. Owner > "Aesthetically its great but only because I spend well over 20 hours editing to make up for the lack of user..." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___3095499) VR Verified Reviewer Business owner > "Occasionally run into customers who aren't comfortable with using it." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___2953744) RK Rachel K. Accounting > "Have used the product in public settings with zero issues." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___4283321) MT Michael T. ownner , acupuncturist > "I do find that sometimes the payouts can be confusing" [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___3554897) CK Colleen K. Rep Trainer > "I like the ability to let the customers use the Tap feature on their credit or debit cards." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___3006387) MA Michael A. Owner > "Back office reporting is not as intuitive as I would expect from how easy it is to use." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___3008156) SD Sherri D. General Manager > "It was a huge improvement as far as ease of use and the time it takes to finish a purchase." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___3851826) MA Melanie A. Business Owner > "A client purchased multiple packages totally thousands of dollars from my company, received the services,..." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___2856217) KK Kasey K. Owner and Operator > "The ability to use this product anywhere at anytime makes it my number one choice for quick business..." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___3330301) MC Michael C. Attorney > "The optional add on devices (such as the terminals) seem pricey to me, which has kept me from ordering them...." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___2346484) VR Verified Reviewer Purchasing Coordinator > "This allows me the option of taking credit cards instead of relying on people having cash." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___3406900) KH Kelsey H. lot manager > "Was very slow and would regularly crash." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___3322087) LK Lynn K. Pastor > "The processing fees were very reasonable for our use. " [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___4146912) John A. Owner > "This took way too many hours to set up. " [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___3095499) JT Jared T. Supervisor > "The user interface of square is very easy to use and can be learned by young employees with little to no..." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___4164636) LM Larry M. owner/Inspector > "I really don't have any thing bad to say about the software or platform except maybe I do wonder about if I..." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___2898284) LB Laura B. First Impressions Director > "The software is easy to manage on the back end and front end." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___3731257) VR Verified Reviewer line cook > "cant find any negative option. but then again i dont know how expensive it is and if it helps match to your..." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___2673719) JM Jay M. Sales and hires > "build quality is important it’s been dropped a few times and still works fine, also charge life is awesome,..." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___3295559) VR Verified Reviewer Director of Delivery > "We've had trouble updating inventory and printing barcode labels." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___2334975) JM Jude M. Owner > "I can also offer discounts, rewards and gift cards from the App." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___3490529) John A. Owner > "Its not intuitive. " [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___3095499) VR Verified Reviewer Purchasing Coordinator > "It is small, easy to use but still allows me to invoice and create reports but still be portable to take..." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___3406900) Victoria W. Data & Finance Mgr > "I found it a little confusing adding items and users at first and feeling assured I would get the result I..." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___2595675) VR Verified Reviewer CEO > "I ma using this and managing it for my customers and I feel like this is the best merchant provider..." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___3528460) MA Melanie A. Business Owner > "Square permits fraudulent chargebacks against your company." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___2856217) AR Angel R. Nail Tech > "It's easy to set up a sale and get paid quickly." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___4503168) MA Melanie A. Business Owner > "Square permits fraudulent chargebacks against your company." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___2856217) RK Rachel K. Accounting > "Simple product, everyone knows how to use it when buying a product." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___4283321) VR Verified Reviewer Director of Delivery > "We have a lot of glitches with the program, despite updates." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___2334975) TT Tracee T. General contractor > "It has opened alot of opportunities and possibilities to my small business that wouldn't have been an option..." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___3092543) DB Daniel B. VP > "Customer service rating is 0." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#GetApp___3021593) JM Jude M. Owner > "Customer's recognize the square device on my phone and feel confident when I process their cards." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___3490529) CV Crayle V. Freelancer > "You can't manage your account from your phone." [See full review](https://www.capterra.com/p/170272/Square-for-Retail/#Capterra___2911045) [View Reviews](https://www.capterra.com/p/170272/Square-for-Retail/reviews/) ## User interface 3.80 (189) [Square for Retail](https://www.capterra.com/p/170272/Square-for-Retail/) 4.67 (493) ## Connect with a Capterra advisor for a free 15-minute consultation Get a personalized software list aligned to your business needs with guidance from our expert advisors. Our team has helped 1 million+ businesses like yours find options that fit their needs. ### Features Windward System Five Top features 47/50 - Accounting Integration - Activity Dashboard - AI Copilot - API - Barcode Recognition - Barcode/Ticket Scanning - Billing & Invoicing - Cash Management - Commission Management - Credit Card Processing - Customer Database - Customer History - Customizable Reports - Data Import/Export - Data Synchronization - Discount Management - eCommerce Management - Electronic Payments - Electronic Signature - Email Marketing - Employee Management - For Retail - Generative AI - Gift Card Management - Inventory Management - Inventory Replenishment - Inventory Tracking - Loyalty Program - Multi-Currency - Multi-Location - Order Management - Payment Processing - Point of Sale (POS) - Price/Margin Management - Pricing Management - Product Catalog - Promotions Management - Purchase Order Management - Real-Time Data - Real-Time Reporting - Real-Time Updates - Receipt Management - Reporting & Statistics - Retail Inventory Management - Retail Management - Returns Management - Returns Tracking - Sales Reports - Sales Tax Management - Sales Trend Analysis [See all features](https://www.capterra.com/p/43189/Windward-System-Five/#features) Square for Retail 36/50 - Accounting Integration - Activity Dashboard - AI Copilot - API - Barcode Recognition - Barcode/Ticket Scanning - Billing & Invoicing - Cash Management - Commission Management - Credit Card Processing - Customer Database - Customer History - Customizable Reports - Data Import/Export - Data Synchronization - Discount Management - eCommerce Management - Electronic Payments - Electronic Signature - Email Marketing - Employee Management - For Retail - Generative AI - Gift Card Management - Inventory Management - Inventory Replenishment - Inventory Tracking - Loyalty Program - Multi-Currency - Multi-Location - Order Management - Payment Processing - Point of Sale (POS) - Price/Margin Management - Pricing Management - Product Catalog - Promotions Management - Purchase Order Management - Real-Time Data - Real-Time Reporting - Real-Time Updates - Receipt Management - Reporting & Statistics - Retail Inventory Management - Retail Management - Returns Management - Returns Tracking - Sales Reports - Sales Tax Management - Sales Trend Analysis [See all features](https://www.capterra.com/p/170272/Square-for-Retail/#features) ### Recognition No recognitions have been awarded to Windward System Five No recognitions have been awarded to Square for Retail ### Deployment & support Windward System Five Deployment - Cloud, SaaS, Web-Based - Desktop Mac - Desktop Windows - Desktop Linux - On-Premise Windows - On-Premise Linux - Desktop Chromebook - Mobile Android - Mobile iPhone - Mobile iPad Support - Email/Help Desk - FAQs/Forum - Knowledge Base - Phone Support - 24/7 (Live rep) - Chat Training - In Person - Live Online - Webinars - Documentation - Videos Square for Retail Deployment - Cloud, SaaS, Web-Based - Desktop Mac - Desktop Windows - Desktop Linux - On-Premise Windows - On-Premise Linux - Desktop Chromebook - Mobile Android - Mobile iPhone - Mobile iPad Support - Email/Help Desk - FAQs/Forum - Knowledge Base - Phone Support - 24/7 (Live rep) - Chat Training - In Person - Live Online - Webinars - Documentation - Videos ### Company Details Windward System Five - By Windward Software - Located in Canada - Founded in 1984 Square for Retail - By Square - Located in United States - Founded in 2009 ## Popular Comparisons [Windward System Five](https://www.capterra.com/p/43189/Windward-System-Five/)[3.80 (189)](https://www.capterra.com/p/43189/Windward-System-Five/reviews/) vs [Epos Now](https://www.capterra.com/p/152638/Epos-Now/)[3.77 (726)](https://www.capterra.com/p/152638/Epos-Now/reviews/) $135/month Price $349one time 3.8 Features 3.8 3.7 Ease of Use 3.8 [View full comparison](https://www.capterra.com/compare/43189-152638/Windward-System-Five-vs-Epos-Now) [Square for Retail](https://www.capterra.com/p/170272/Square-for-Retail/)[4.67 (493)](https://www.capterra.com/p/170272/Square-for-Retail/reviews/) vs [Square Point of Sale](https://www.capterra.com/p/275802/Square-Point-of-Sale/)[4.64 (3,032)](https://www.capterra.com/p/275802/Square-Point-of-Sale/reviews/) $0/month Price $0/month 4.5 Features 4.5 4.7 Ease of Use 4.7 [View full comparison](https://www.capterra.com/compare/170272-275802/Square-for-Retail-vs-Square-Point-of-Sale) [Windward System Five](https://www.capterra.com/p/43189/Windward-System-Five/)[3.80 (189)](https://www.capterra.com/p/43189/Windward-System-Five/reviews/) vs [Shopify](https://www.capterra.com/p/83891/Shopify/)[4.54 (6,698)](https://www.capterra.com/p/83891/Shopify/reviews/) $135/month Price $29/month 3.8 Features 4.4 3.7 Ease of Use 4.5 [View full comparison](https://www.capterra.com/compare/43189-83891/Windward-System-Five-vs-Shopify) [Square for Retail](https://www.capterra.com/p/170272/Square-for-Retail/)[4.67 (493)](https://www.capterra.com/p/170272/Square-for-Retail/reviews/) vs [Epos Now](https://www.capterra.com/p/152638/Epos-Now/)[3.77 (726)](https://www.capterra.com/p/152638/Epos-Now/reviews/) $0/month Price $349one time 4.5 Features 3.8 4.7 Ease of Use 3.8 [View full comparison](https://www.capterra.com/compare/152638-170272/Epos-Now-vs-Square-for-Retail) [Windward System Five](https://www.capterra.com/p/43189/Windward-System-Five/)[3.80 (189)](https://www.capterra.com/p/43189/Windward-System-Five/reviews/) vs [RetailEdge](https://www.capterra.com/p/76636/RetailEdge/)[4.77 (188)](https://www.capterra.com/p/76636/RetailEdge/reviews/) $135/month Price $495one time 3.8 Features 4.6 3.7 Ease of Use 4.7 [View full comparison](https://www.capterra.com/compare/43189-76636/Windward-System-Five-vs-RetailEdge) [Square for Retail](https://www.capterra.com/p/170272/Square-for-Retail/)[4.67 (493)](https://www.capterra.com/p/170272/Square-for-Retail/reviews/) vs [Clover](https://www.capterra.com/p/226864/Clover/)[3.77 (576)](https://www.capterra.com/p/226864/Clover/reviews/) $0/month Price Contact vendor for pricing 4.5 Features 3.8 4.7 Ease of Use 4.0 [View full comparison](https://www.capterra.com/compare/170272-226864/Square-for-Retail-vs-Clover) [Windward System Five](https://www.capterra.com/p/43189/Windward-System-Five/)[3.80 (189)](https://www.capterra.com/p/43189/Windward-System-Five/reviews/) vs [PayPal](https://www.capterra.com/p/207944/PayPal/)[4.65 (26,504)](https://www.capterra.com/p/207944/PayPal/reviews/) $135/month Price $0.29 3.8 Features 4.6 3.7 Ease of Use 4.6 [View full comparison](https://www.capterra.com/compare/43189-207944/Windward-System-Five-vs-PayPal) [Square for Retail](https://www.capterra.com/p/170272/Square-for-Retail/)[4.67 (493)](https://www.capterra.com/p/170272/Square-for-Retail/reviews/) vs [Shopify POS](https://www.capterra.com/p/205337/Shopify-POS/)[4.56 (242)](https://www.capterra.com/p/205337/Shopify-POS/reviews/) $0/month Price $5/month 4.5 Features 4.5 4.7 Ease of Use 4.6 [View full comparison](https://www.capterra.com/compare/170272-205337/Square-for-Retail-vs-Shopify-POS) [Windward System Five](https://www.capterra.com/p/43189/Windward-System-Five/)[3.80 (189)](https://www.capterra.com/p/43189/Windward-System-Five/reviews/) vs [Lightspeed Retail](https://www.capterra.com/p/120491/Lightspeed-Retail/)[4.03 (975)](https://www.capterra.com/p/120491/Lightspeed-Retail/reviews/) $135/month Price $109/month 3.8 Features 3.9 3.7 Ease of Use 4.1 [View full comparison](https://www.capterra.com/compare/43189-120491/Windward-System-Five-vs-Lightspeed-Retail) [Square for Retail](https://www.capterra.com/p/170272/Square-for-Retail/)[4.67 (493)](https://www.capterra.com/p/170272/Square-for-Retail/reviews/) vs [Odoo](https://www.capterra.com/p/135618/Odoo/) [4.20 (1,314)](https://www.capterra.com/p/135618/Odoo/reviews/) $0/month Price $31.1/month 4.5 Features 4.2 4.7 Ease of Use 4.0 [View full comparison](https://www.capterra.com/compare/135618-170272/Odoo-vs-Square-for-Retail) [Windward System Five](https://www.capterra.com/p/43189/Windward-System-Five/)[3.80 (189)](https://www.capterra.com/p/43189/Windward-System-Five/reviews/) vs [Meevo](https://www.capterra.com/p/172058/Meevo-2/)[4.37 (277)](https://www.capterra.com/p/172058/Meevo-2/reviews/) $135/month Price Contact vendor for pricing 3.8 Features 4.3 3.7 Ease of Use 4.3 [View full comparison](https://www.capterra.com/compare/43189-172058/Windward-System-Five-vs-Meevo-2) [Square for Retail](https://www.capterra.com/p/170272/Square-for-Retail/)[4.67 (493)](https://www.capterra.com/p/170272/Square-for-Retail/reviews/) vs [Lightspeed Retail](https://www.capterra.com/p/120491/Lightspeed-Retail/)[4.03 (975)](https://www.capterra.com/p/120491/Lightspeed-Retail/reviews/) $0/month Price $109/month 4.5 Features 3.9 4.7 Ease of Use 4.1 [View full comparison](https://www.capterra.com/compare/120491-170272/Lightspeed-Retail-vs-Square-for-Retail)