Windward Maintenance Contract / Cloud Subscription

Windward Software created Windward System Five, our flagship business management software in 1984.  Since then we have been committed to continuously improving our product by developing features and functionality for all industries.

The Windward Maintenance Contract is a standard annual business expense for all Windward System Five users.  Windward Software is in business to support your business, and this plan allows us to bring value to you when you need us most.

Where does your yearly spend go?

We often get asked what's included in your yearly spend.  The answer is largely the same for our Cloud and Locally hosted customers when it comes to product enhancements, access to Customer Care and Advanced User Training such as Windward Webinars and the Windward Learning Academy.  Our cloud customers enjoy some added benefits which are listed in the section for Cloud Subscriptions below.

Why settle for an outdated version of your business management solution, Windward System Five, when you can experience the most recent, most powerful solution?  Secure the future of your business by renewing your maintenance plan today! Call your account manager at (800) 663-5750

Keep scrolling for details regarding Windward System Five Enhancements, Customer Care, User Education and Training and Cloud Subscriptions.

  • Windward System Five Enhancements
  • 24/7 Access to Customer Care
  • User Education and Training








Windward System Five Enhancements

Custom Modifications, if beneficial for a wider audience, usually
make their way into General Releases. If an enhancement requires a work-flow consultation, Professional Services are available for a charge. Most functionality listed is part of your product updates, with the exception of Integrations and Major Modules.  Check the release notes to see what's new.

Prioritized by customer impact, we assure full time resources are dedicated to fixes of System Five. While defects are an inevitable part of software development, the best way to prevent them is to find them pre-release. We have multiple QA staff who test functionality and report back, and are increasingly using regression testing to help automate and enhance our Quality Assurance Testing processes.

We have recently undergone extensive training and certification with Microsoft directly. We are now certified Gold for Application Development, Silver for Data Analytics, and Gold for Cloud Platform, which means we build solutions to work best with the standard business tools you already use today. Check this link to see the certifications we've obtained.

For those who opt to use integrated credit and debit card processing, there is a substantial verification process required for software vendors to assure certification. Windward Software has maintained PCI certification, this focus on the protection of information and safeguarding data is absolutely paramount.

Make sure you understand your part in being PCI Compliant by clicking here.








24/7 Access to Customer Care


We maintain a 24/7 Support schedule, balancing the resources based on the volume of inbound activity. Note that we have moved some activities such as installs and product updates to be scheduled outside of North American business hours. This helps us be available when you need us.  

Connect with customer care using the below methods:

By Phone

Best for urgent tickets 

Our "First Responder" initiative is now in play, assuring the majority of tickets are resolved on the first call.

Dial +1(800) 663-5750

By Email

Suitable for less urgent inquiries

Specifically useful when screen shots and additional context is required

click here to launch an email to support@windwardsoftware.com

By Microsoft Bookings

Find the right time for your business update, and book your own support appointment


Access to Training Dataset

One tool we find is under-utilized (at least past Go-Live) is the use of a training dataset. Having access to a 'sandbox' version of your system is very important for testing work-flow changes, new functionality, and validating updates before you put them into Production. Give your new employees access to the training area to the work-flow for their role. 

Email support@windwardsoftware.com to copy over your dataset to training.

Management of Supported Hardware

Understanding what devices and accessories are supported with Windward System Five is important for you to get the best return on your software investment. If you aren't currently utilizing barcode scanners, cash-drawers, or other peripherals that would help in practical deployment, please see the provided link.

Escalation to Programmer

If there is an incident the Customer Care team can’t figure out, we offer consultation with the programming team.











Windward Education and Training

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Windward Webinars

Our Webinar schedule, which focuses on various product and workflow topics, are held bi-weekly.

Available only for customers on Maintenance or Subscriptions (On-Cloud).

Windward Learning Academy

This online learning platform is available to help you and your staff learn the software. The Academy has topic and role based learning plans that include quizzes to engage your staff in the learning process.

 Log into the Windward Learning Academy here


Searchable Self Help

Quick Reference guide that has been indexed for easy access to your questions.  Available for when you need a quick answer.

Access Searchable Self Help

Consultative Professional Services are also available for advanced training that is not included in Maintenance: https://www.windwardsoftware.com/resources/professional-services.html









Windward Cloud Subscriptions

System Five on Cloud Subscriptions

System Five on Cloud includes all of the above and then some.  Windward has moved to Windows Virtual Desktop Services, managed by Microsoft in Azure.  Our cloud subscribers get Automated Windows Updates, Automated Backups, and Dedicated Security Personnel who consult with industry leading cybersecurity experts.  

A subset of our cloud subscribers are the first to get new features deployed and are on the fast track to native cloud.  Some have even been selected for and have volunteered to get involved with our Azure SQL Preview.




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Windward Intelligence

Windward Intelligence is a Sales Analysis tool allowing you to quickly view and drill-down into Gross Margins and Sales by Category, Salesperson, and/or Region. (requires Microsoft Power BI license)  

This is available exclusively for our cloud customers as part of their subscription.  Learn more about Windward Intelligence by clicking here.

Try out Windward Business
Management Software for yourself!

No credit card required.

Try Windward for Free

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1 (250) 492-8888


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