Windward System Five Reviews

“strong features and great value”

Pros

Value is really good and the software turned out to be much more capable than I expected. It handles inventory tracking, private customer information management and invoicing very well.

Cons

The interface feels outdated and buggy which makes it harder to take full advantage of everything it can do. It also has occasional long loading times, plus those notifications about users connected to different hardware can get pretty annoying.

“expensive mess with awful support”

Pros

There's no denying System Five is incredibly versatile and packed with functionality. If you need a feature, it probably already has it. The interface is great and since we run it on-premises, performance is usually acceptable, although with more than 20 years of accumulated data some reports have started to run slowly.

Cons

At the same time, almost nothing seems to function the way it should. The support has been terrible at every level and the pricing is outrageous, literally 22.5 times higher than the software we tested as a replacement. On top of that, getting away from it is incredibly difficult because the database structure feels completely chaotic, like a dump truck full of spaghetti. Trying to export our data has been an absolute nightmare.

“flexible setup and POS-friendly platform”

Pros

Compared with QuickBooks and other accounting programs, this one feels different but that difference really works in its favor once it's set up around your business needs. After you learn how it works, it stands out clearly, especially because it fits POS use much better than many traditional accounting systems.

Cons

One issue is the bugs that sometimes cause the system not to update properly. It also leans more toward being POS-friendly than accounting-focused. Without a great understanding of how it works, it can create problems in the data so stronger training would help a lot, especially for long-time older users who may still struggle with the system.

“inventory and purchasing done right”

Pros

Inventory management and purchasing are handled really well and there are a lot of extra features included that make the software even more useful overall.

Cons

Form creation is where it falls short. The process is complicated and takes far too much time to get through.

“Strong features with key pricing limitations”

Pros

There are quite a few useful features in the system, especially when it comes to functionality and tracking capabilities.

Cons

One thing that had to be added later was a "wildcard" search for part numbers after we were initially told the system didn't support it. Oddly enough, wildcard search already existed for descriptions, just not for parts. And like many others have mentioned, every update feels unpredictable because you never know what will be impacted afterward. The most frustrating limitation is the lack of a pricing matrix with variable rates based on cost. I can create different markup percentages by supplier, subcategory and other fields but I still can't build a pricing structure where the percentage changes as cost increases. A $1.00 item might need a 300% markup, while a $1000.00 item obviously would not, yet that capability simply isn't available. Both the System 5 support team and the account manager responded as if this was some unusual request that no one had ever asked for before. I was even told we could pay extra just to speak with someone who would ultimately tell us they didn't know how to make it happen. The frustrating part is that I moved over from Winworks because we had outgrown it and even that system offered this function to a much better degree. Credit to the sales team, though, they were very confident in saying this system could handle everything we asked about at the beginning.