A Holiday Story: How Windward Software Came to Be

A Holiday Story: How Windward Software Came to Be
A story for the ages.

Windward Software began when founder and CEO, Dennis Jacobsen, created a business software solution for a single furniture store in Northern British Columbia, back in 1984.

Like other software success stories of the early days, this one also began in a basement, with one man, one computer, and a shoestring budget.

After graduating from college, Dennis and his wife, Jean, a nurse, were raising their two little girls in a small town on the edge of the vast Canadian wilderness.

The economic crash of the early 1980’s made it difficult to find work in his career as Civil Engineering Technologist, so Dennis began selling and installing satellite dishes and opened a computer store, “Family Computing,” with his friend, Phil Wright.

In 1984, Dennis and Phil closed the store and each created a solo business based on their own areas of expertise.

In the meantime, Dennis focused on software, spending his time in his basement writing code to help a local stationary store run their business.

Within months, he offered his software and programming services to a local furniture store to help them manage their inventory, and Windward Software was officially launched.

He quickly discovered that every business problem he solved for the furniture store led to a new set of challenges.

From -35 to +35 degrees (Celsius)

To be closer to family, the Jacobsens moved Windward Software to Penticton, British Columbia, in 1990, where Dennis hired a full team of developers, sales, and technical support experts.

To this day, the Windward Software headquarters is located a block from beautiful Skaha Lake Beach, in the heart of Okanagan Wine Country. And several of those original programmers still work for the company.

In 2011, Windward Software bought out Phil’s company and launched the Windward Software office in Brisbane, Australia. After almost 30 years of doing business with Dennis, Phil became a Windward employee.

To this day, Phil’s skills in implementation, advanced support and sales, are a vital contribution to the five-person Windward team in our “Down Under” office.

In 2008, Windward opened a full-scale office next door to Microsoft and Apple in the famous Cebu IT Park, in Cebu, Philippines. Today, the staff of 50 dedicated, highly skilled IT professionals, enable us to offer 24/7 technical and implementation support to customers around the globe. Many have been with Windward since Day One.

No matter where we go in the world, Windward Software continues to improve our products and services by focusing on our original Core Values of providing our customers with a fully integrated business management system, owning our technology, and offering custom development.

All while remaining true to our motto of “We help you run your business, instead of just reporting on it.”

What's in a name?

Looking back, Dennis likes to tell the story of how the name, “Windward Software,” came about.

In 1988, while still living in Northern British Columbia, Dennis looked out the window on yet another cold, snowy day. Outside, it was -35 C ( -31 F), and Dennis thought, “There has to be a better way to make a living.”

Then it hit him that he could support his customers from anywhere in the world, just using a phone, fax machine and modem.

Nor had cell phones, let alone Smart phones, and very few people had a personal computer.

In fact, Dennis’s vision of a business owner being able to be physically away from their business, yet still connected, was quite futuristic.

He wanted to share this vision through his fledgling software company, and felt that the company needed a name that reflected it.

He and Jean had enjoyed a trip to Barbados a few years prior, and the idea of sitting on a beach instead of at the office was appealing.

Unfortunately, “Barbados Software” just didn’t have a great ring to it…

So, Dennis and Jean literally looked through an encyclopedia for ideas. (For the younger set among us, that’s the thick, informative set of books that every family owned prior to the internet.)

Where are they now?

Today, Dennis and Jean’s daughters have grown up, and they now have two granddaughters. Jean has long since retired from nursing.

Although he and Jean recall their original vision of being able to simply run the company from a beach, Dennis remains strongly at the helm of Windward Software, now a thriving international software company.

When he’s not traveling to the Chicago, Cebu and Brisbane offices, you’ll find Dennis showing up every morning to his corner office overlooking Skaha Lake, like he has for almost three decades.

In line with their personal commitment to community service, Jean and Dennis are more active than ever in the Penticton Okanagan Rotary Club. Jean just completed a term as Club President, and Dennis helps coordinate the region’s International Rotary Exchange Student Program.

To top it off, Dennis chairs the Board for a favorite local music venue, where his business management skills and donated software have helped secure the future of this beloved venue.

After sixteen years in business, The Dream Café has a reputation as “THE place to play” when touring the Okanagan, and enjoys packed houses at almost every show. In fact, it was recently named one of the “35 Best Blues Clubs in Canada.”

Today, Windward Software is a trusted software provider to over 4,000 businesses and tens of thousands of users across 35 countries.

In all, over 15,000 Windward-powered terminals around the world process over $1.5 billion in sales annually.

Our Penticton, BC, office houses over half of our 100 employees, including the entire Microsoft Gold Certified Development Team; as well as the Canadian Sales and Marketing, Implementation and Training, and Advanced Support teams; and of course, Dennis and the Windward Executive team.

But we never forget our humble beginnings, and how we got here:

By always answering the phones with a real person.

By courteously and reliably serving our customers.

By solving their problems.

By focusing on continuous improvement.

By sharing what we learn.

And by keeping family and community service at the core of our values and actions.

Today, we may not have all of our offices on tropical islands, but we definitely know how to make your business challenges disappear into the breeze. 

And, we can show you how to get your time back from the thousands of daily tasks that can easily be automated by our software.

If you're looking for the freedom that a robust business management software can provide you, backed by a software company with decades of experience in helping businesses just like yours to succeed, give us a call today: +1 (800) 663-5750.

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