The World’s Most Adaptable Sales & Management Software

Designed for ultimate smooth sailing —
configured for your business in your specific industry.

Easy to learn software helps you run your business, instead of just reporting on it. It grows with you.

Trusted since 1984 by 4000+ clients in 35 countries. 24/7 global live support, training, and resources.

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Manage your business better with Windward System Five

Manage your business better with Windward System Five

SELL more, and track results

Windward’s Business Management Software is extremely adaptable and is equally at home handling simple payment processing or specialized functions like bar code scanning, serial number tracking, unit tracking, labour costs, alternate suppliers, signature capture, and more. Our platform has been built with the feedback of business owners in over 20 industries with decades of refinement. Our feature set is unparalleled.MANAGE from 30,000FT.

Organize staff, customers, inventory, and operations with a comprehensive toolset.

ANALYZE your business.

Gain the visibility that business owners crave through top-level and detailed reports. Knowledge is power.

GROW as needed.

Add modules, integrate with other software, go cloud-based, multi-store, or sell globally online. Windward’s Businss Management Software grows with you.

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Trusted since 1984 by 4000+ clients in 35 countries.

Core Software Features

Windward System Five is a complete business management package configured for your business in your specific industry.

Point of Sale

Engage customers and increase profits by equipping your sales staff with the tools and knowledge they need to provide an exceptional level of customer service.

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Enjoy greater inventory control with barcoding for faster checkout service, improved customer satisfaction, fewer errors and quicker stock checks.

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Signature Capture

Reduce paperwork, streamline administrative processes and incorporate a higher level of security with our POS software’s electronic signature capture capabilities.

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Multi-store POS

Keep your business network running smoothing and cohesively with our dealer management software. Oversee your operations from a single location and communicate business critical information between branches.

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Mobile POS

Mobile POS solutions enable your employees to sell more effectively and provide customers with an enhanced retail experience. Handheld devices make things simple.

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Credit Card Processing

With Windward Software’s integrated credit card processing, you’ll be able to conduct credit, debit and gift card transactions quickly, accurately and securely.

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Business Management

Buy better, market smarter and work more efficiently in your business. Windward System Five provides you with the knowledge and control to drive profits.

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Inventory Control

Control your inventory, track inventory movement, optimize stock levels and improve your cost control measures through reports.

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Customer Management

Create a database with your customer information to provide a smoother, more personal shopping experience, and increase your selling and marketing opportunities.

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General Ledger

Windward Software's integrated accounting software allows you to view, print, enter and report data quickly and conveniently, providing and simple, error-free way of managing your books.

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Serial Number Tracking

For businesses that require that extra level of inventory management, our software provides serial number tracking capabilities so you know where your product is at all times.

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Admin & Control

Empower your employees with the access and information they need to perform their jobs properly, without compromising security or confidential data.

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Email Marketing

Windward’s email marketing tools let you connect with your customers so you can generate targeted leads that drive successful, profitable and more intimate customer relationships.

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Give your staff the tools they need to process payroll efficiently. From automatically creating accounts payable invoices to generating up-to-date financial reports, our accounting software does it all.

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Financial Reporting

Track and compare company performance with P&L statements. Use balance sheets to determine your financial standing.

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Customer Reporting

Get remarkable insight into the people that matter most to your business - your customers. Slice and dice customer data 100s of ways to optimize processes.

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Create Your Own Reports

The beauty of Windward's custom report designer is that you can analyze the details that matter most to you... whether that's staff in multiple locations, inventory levels, and another area of interest.

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SMB & Enterprise Editions

Windward System Five is available in two versions: SMB lets you choose the modules you need most. Enterprise comes fully loaded to provide the most comprehensive business management system available.

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Installed or SaaS

Choose from two options for deploying our ERP software: through a tried and tested local installation, or by using our innovative cloud-based Software as a Service (SaaS) model.

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Software Integrations

Configure Windward’s business management software to handle industry-specific processes and integrate with systems you already have in place.

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Recommended POS Hardware

Windward System Five point of sale software supports a range of optional hardware to help your business run smoothly - scanners, printers, computers, touch screens, and more.

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Fail Safe Technology

Whether you need reliable backup to protect against system failure, or you need to synchronize information across multiple locations, Windward’s fail safe technology has got your back.

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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.

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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.

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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.

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Real customers, real results.

Cole Haddad

Valley Moto Sport

We've been a user of Windward Software since 1992. When we originally bought it, it was important to the business to have something that could track all…

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Jason Scalise

Broadway Wine and Spirits

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.…

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Classic Health

We've been using Windward Software for about 2.5 years now. We are getting great support. We also designed a component for our industry that was special.…

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Try out Windward Business
Management Software for yourself!

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