Expert Support

Windward offers phone support, virtual assistance through screen sharing, or on-site support depending on edition and plan. Self-help is always available 24/7 through our extensive knowledge base.

Customer Care Portal


Our comprehensive training materials are available for all customers. Whether you're just getting going or just need to train a new employee on one thing, you'll love the video library and how-to's.

Windward Learning Academy


Maintenance and support packages are available for customers that like an ongoing support team available to fine tune software features. Our experts will handle the software issues so you can focus on your bottom line.

Maintenance Contracts

Real customers, real results.

"Windward is a great software system that does A LOT. Fairly intuitive and easy to learn. It has many features that helps keep users organized and on track!" -Christine Williams
- Christine Williams
We made the switch to Windward System Five from our previous system, Activant​ Dimensions. With our old system, we had a complicated three-part invoice, and we would give the customer one copy. But, now we have the ability to use a modern printer and print actual paper.Now I've had customers regularly say to me, "thank you for giving me something I can actually write on!"A Windward Implementation Specialist was assigned to our business, and we were provided with a dedicated site, which included a custom training curriculum. The Windward Learning Academy videos are fantastic!Switching to Windward System Five has been a very fluid transition.
- Caitlin
The business has grown so much that without Windward's software solution, we simply could not function effectively! The software has become our business management foundation.
- Robert Hibbert, GM
We bought Windward 2 years before we implemented it and I wish we would have implemented it sooner because it does a lot better reporting. We were using Quickbooks before and it didn't integrate with our POS... It eliminated additional expenses for us and I think it works really well...
- Shea Miller
Prior to Windward Software, we used a collaboration of 3 different programs. We had TomCash point of sale. We used QuickBooks for our accounts payable. In addition, we had PCCharge Payment server for our credit card processing. Just the functionality of all 3 together was terrible. I felt like an IT guy. It would take 3 days per week for me to find out how much cash we had.Since we put in [Windward Software], it just bought me 3 days per week - cleared them right up. Every day I can report my deposits, clear all my cash accounts, stay on top of the money. It also gives me the time to focus on researching what our customers are buying, coming up with ways to implement reports, finding price points, and just buy better.
- Jason Scalise
Windward Software's Rental POS Edition has revolutionized the way we do business. It allows us to track the full history of every single item: rentals, repairs, warranty, sale date, owner, etc. If a barcode does not come with the item from the manufacturer, it is easy to generate one using the Windward solution.
- Jim Pedulla
“Windward helps our business in all areas of the operation. Without Windward, it would be like driving in the dark with no headlights.” -Travis Green
- Travis Green
It got people in the store and many people bought more than just the antifreeze; it’s hard to put dollar value on that!
- Debbie Ross

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