About Windward Software

We help you run your business, instead of just reporting on it.

Headquartered in Canada, Windward Software has been in the business since 1984. Our client base includes businesses throughout the world.

"Windward Software is the most flexible and user-friendly business management system on the market today."

We are specialists in inventory control, point of sale, invoicing and accounting software systems for the retail and customer service industries. Using a series of soft switches, Windward Software ERP software adapts to the way you do business. Unlike many of our competitors, we don’t believe that a company should have to change its existing business practices to suit a software package.

Windward Software has been in the business since 1984, and our client base includes businesses throughout the world. Our clients are based in Canada, United States, Australia, Barbados, Cayman Islands, Jamaica, Bermuda, Philippines, Malaysia, Brunei and many others.

The Developers of Windward Software

We’ve gained extensive experience over the years, and have learned that every business is unique and that a sound business software solution must accommodate the user and their needs. With Windward’s ERP software, you can configure the system with soft switches to make the system work the way you need it to.

"Our goal is to make this software easy and fast to learn. We do this with Windows technology for point-and-click operation while still employing keyboards, barcode scanners, macro keyboards, weigh scales and other time-saving point of sale hardware devices."

Our Management Team

Dennis Jacobsen

Dennis Jacobsen

CEO
Erna Hansen

Erna Hansen

COO
Rod Penway

Rod Penway

CFO
Kevin Schilter

Kevin Schilter

Director Worldwide Sales
Mark Rutter

Mark Rutter

Marketing Manager
Derek Gillespie

Derek Gillespie

Product Development Manager
Jeff Watson

Jeff Watson

Client Services Manager
Charlene Gillespie

Charlene Gillespie

E-Learning Manager
Sharon Brum

Sharon Brum

HR Manager

Trusted since 1984 by 4000+ clients in 35 countries.

Progression

We’ve kept ahead of the competition by creating ERP software that features e-commerce, email marketing, payroll, manufacturer parts catalogs and electronic purchase order systems. We’ve also developed strategic partnerships with credit card processing systems and other reputable organizations to provide the best service possible.

Our knowledge is deep and our software is strong. Our ERP software has hundreds of features, ensuring that your business management software functions they way you need. And because we don’t just sell the software, but design and build it as well, if we don't have the feature you need, we can make it for you.

Here are some other tidbits you might not know about Windward Software and the business management solutions we provide our clients:

  • We’ve been in business since 1984
  • We have an  A+ rating with the Better Business Bureau
  • We offer 24/7 technical support to our customers
  • We are a certified Microsoft Partner with a Gold Application Development competency
  • We have sold our ERP software solutions to more than 4,000 clients in 35+ countries
  • There are Windward Software clients in every state, territory and province in the United States and Canada.
  • We’ve been named Best Software Development Company three years in a row.
  • After implementing our software solution, we ask our clients how we did.  Our average rating is Grade A
  • There are over than 10,000 Windward stations operating worldwide, processing more than $1.5 billion in sales annually
  • We have internal certification programs for our employees to provide you with the highest level of service
  • Our enterprise Windows software, Windward System Five, started development in 1998
  • We do business without three-year contracts, and you own and control your data and ERP software licensing
  • Our Windward Software solutions are PCI certified (Payment Card Industry)
  • Windward System Five is BIR accredited (Bureau of Internal Revenue)
  • With any support call, the first five minutes are complimentary
  • Our clients include Canadian and US universities, as well as the US government
  • Our head office is located in Penticton, BC in a geographically stable area of Canada (no hurricanes, earthquakes, flooding, tornadoes or tsunami disasters)
  • We have a second office located in Cebu City, Philippines and Brisbane, Australia that allows us to offer extended support hours for our Australian and Asian clients
  • Our office in Chicago allows us to offer workshops closer to our central and eastern clients
  • We have more than 100 people helping to build, maintain and service our clients
  • Collectively, our dedicated staff has a brain trust of more than 250 years of ERP software experience, and we use it all to help you succeed
  • We support all of our customers, even those running older and legacy versions of our software solutions
  • We have invested in an in-house training facility and offer workshops and user conferences regularly
  • Our customers have access to more than 1,500 training videos and 3,400 pages of documentation
  • Our ERP software accounting module stores up to 39 years of financial data, with the ability to reprint and report back to year one
  • We have business experience in several sectors to help make you succeed (computer, lawn and garden, lighting and furniture showrooms, liquor stores, sporting goods, hardware, rental, outdoor power equipment, powersport, marine equipment and the medical industry, as well as other retail and wholesale businesses)
  • Our tagline is “We help you run your business, instead of just reporting on it.”  Call us toll-free at 1(800)-663-5750 to discuss how we might be able to help you.

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