Windward Software

Windward System Five

by Windward Software

Who Uses This Software?

We help small to medium sized retail/wholesale companies gain control of their business. Windward System Five is fast and easy to use.

Average Ratings

  • Overall
  • Ease of Use
  • Customer Service

About This Software

When it comes to business process demands, rental companies have some very unique requirements. Windward's RentalPOS Software has been specifically designed to meet these unique challenges. Rental Point of Sale addresses such demands as tracking of rental inventory, processing of rental orders, issues and returns, servicing of rental equipment, and rental billing all while providing a complete Business Management Solution.

Product Details

  • Free Trial
  • Deployment
  • Training
    Live Online
    In Person
  • Support
    24/7 (Live Rep)

Vendor Details

  • Windward Software
  • Founded 1984

Features Checklist

  • Accounting Integration
  • Contract Management
  • Credit Card Processing
  • Customer Accounts
  • For Equipment Rental
  • Inventory Management
  • Maintenance Management
  • Notifications
  • Reservations Management
  • Sales History
  • Scheduling
  • Short / Long Term Rental

Product Reviews

Review This Product!
September 18, 2014

I ask for test this software

Ease of Use
Customer Service

Comments: I ask for test this software,
send to me more information

Vendor Response

by Windward Software on September 22, 2014

Thank you for your interest Haitham. Capterra does not share your email information. If you email us at we can send you a trial. We have several trial versions available for you to evaluate our solution. If you share the type of business you are operating we can send you the right trial version.

Show full comments

Haitham Youssif, IT at EIO

September 08, 2014

A comprehensive all-in-one Retail Business solution

Ease of Use
Customer Service

Comments: We have been using Windward System Five software to handle our Point-of-Sale, Accounting and Inventory systems for a decade. We find that their software is secure, robust, and has many great reporting features for detailed analysis which range from inventory reports, to customer/product sales reports and charts. They have excellent customer and support services- both technical and feature wise. I would like to see better chart and graph options for financial and inventory analysis and report printing. I think they could also streamline their online tutorials and teachings to make it easier for business owners to train their staff - new and old! Overall we find Windward to be a reliable company with proven software that we use everyday in our business.

Show full comments

Dustin Knapp, General Manager at The Wickertree - Home & Patio

August 29, 2014

Total Battery Review of Windward (

Ease of Use
Customer Service

Comments: I have been using Windward for my company for almost 10 years.

I find it the most robust and scalable system that can adapt to any changes that my company grows into.

We currently run a distribution centre, 5 branches and an online store through windward.

I find the tech support much improved over the past few years and the annual upgrades have always been responsive to the changes in the business environment and our company needs.

The system is very easy for new hires to adapt to and its has such depth in product content that there are still many features we have yet to employ. I see it as one of the most versatile POS/CRM/INVENTORY management systems out there.

Being an inventory based company there is nothing more you can ask for from Windward as the system covers all types of views, reports and analysis tools that we require.

I recommend Windward to any growing company that has multiple locations or plans for future expansion

Show full comments

Alan Simpson, President at Total Battery Group of Companies

August 27, 2014

Great product straight out of the box!

Ease of Use
Customer Service

Comments: My company has used the Windward software since 2006 and we have been very impressed with its short learning curve for new employees and powerful reporting system for the back-office. Compared to our previous customized software, Windward has saved us time and money at POS, EOM reporting, inventory controls and vendor/customer maintenance. Windward has been an extremely dependable product and we are very pleased with their support.

Pro: No software customization needed for our company. Everything worked right out of the box.
Cons: They were a little hard to find and had limited user reviews when we were doing our research back in 2004-2005. I wish we would have made the move a year or two earlier.

The employee time sheets, rental module and training database are great for our multi-location company. We run 1 distribution center and 4 retail stores with this software.

Show full comments

Kevin Mathis, Operations Manager at A&G Turf Equipment, Inc

August 27, 2014

Windward System Five

Ease of Use
Customer Service

Comments: Very good product. Capable of handling all of our needs. Very user friendly. Customer service is timely and very knowledgable.

Show full comments

Jeff Boudreaux, VP of Finance at Stranco

August 25, 2014

Windward general POS processes

Ease of Use
Customer Service

Comments: After using Windward for 2 years, we realize it has a lot more to offer than POS and basic inventory, customer and accounting management. It is very in depth and even though we found it very adaptable to our business, it has so much to offer that we are constantly expanding (or changing) our business processes. We were surprized at how quick the implementation team started us up, we were invoicing within 4 days. Tech support is readily available when needed, usually we have mis-coded some inventory or made a mistake with tendering an invoice, but so far, we are happy with the support we received. Over all we are quite satisfied and even though we have had some challenges, given the choice again, we would chose Windward.

Show full comments

Steve Flaman, Manager at Flaman Sales LTD

August 06, 2014


Ease of Use
Customer Service

Comments: Paid for on site set up.
switches to off shore support pretty fast. Harder to communicate after that.
at the 5 month mark we pulled the plug. could not get reports needed for accounting dept nor AR. solicited us as a Gun company with lots of promises. 25k down the drain.

Show full comments

George Smith, President at EGW inc.

January 06, 2014

Best Value

Ease of Use
Customer Service

Comments: Although the implementation of this solution is a lot of work, I have been through others in the past and this one was not much different. You do have to pay extra if you want them to come on site and help, otherwise you are left to watch videos and meet on the phone/over the PC with them. They did help build out a custom learning curriculum for us and help facilitate the learning for my staff which was appreciated.

I do believe that you would be hard pressed to find a better value out there though. This program offers pretty much everything (and then some), from the front of the store POS to the back end accounting. It sounded based on another review that they had some growing pains with their payroll but we've found it works fine/as expected. My staff appreciate the direct deposit.

Support after implementation seems OK. "Regular" support is mostly out of the Philippines but I had a register go down and they did not hang up the phone until we were resolved, eventually getting transferred to their "advanced" support which appeared to be from North America.

Why I purchased this solution over others though, was that in the design of the software and philosophy of the company they really seem to come from the entrepreneur's perspective. From integrated real time accounting and fantastic reporting capabilities and lots of customizability in the software to what their sales guy told me about a core value there: with respect, the customer isn't always right....Lord know's that's true! (in fact I was going to delay the project and when they pushed back I was a little shocked but I'm glad they did). I should also add that my IT guy put some serious analysis into this project and by the facts/spread sheet, they came out on top feature for feature.

Best Value
Does virtually everything
Good emergency support (and 24/7)

mediocre "regular" support
watching training video's is not fun

Show full comments

Darrell W at DW Supply

November 08, 2013

So So - Customer Service -5

Ease of Use
Customer Service

Comments: This program is easy to utilize and when implemented correctly and completely would adequately assist in the day to day processes of running a small business but with so many other packages out there, they might be better value and worth looking at.
Had issues with there payroll program being firstly a skeleton of a program and 8 months behind its delivery time, was hell trying to get assistance I also had to help with the development as it wasn't set for the Australian market, Support is Malaysian based which can be frustrating at times, following is just a line of the response from the Ceo Dennis, "If I am mistaken, tell me your problems right now, today, not
problems way back in time. Get to the point." As i stated, other programs may be a better option when this is the attitude from the Ceo of the company.
Implementation is based on a video library with you being expected to do a lot of the form creation, data importing etc yourself, the video library will take 60 odd hours to complete.
There has been no real structure on implementation and once your running you will need to refer to the video library to work out the accounting package yourself.
Hope this helps with your choice of what Windward offers

Show full comments

Fj .. at Healthcare