Windward Software Owners Retire, Sell Business to Volaris Group

Dennis and Jean Jacobsen – who co-founded Windward Software Inc. in Chicago 35 years ago as a tool to help small to mid-size businesses – have retired and sold their company to British Columbia, Canada-based Volaris Group, which is part of Constellation Software Inc. (CSI), one of the largest publicly traded technology companies in the world. The deal closed on July 1 and the new name is Windward Software Systems Inc.

Volaris Group’s strategy is for long-term growth by offering its companies the ability to achieve growth objectives while retaining independence and focusing on the needs of customers and employees.

In a letter to customers, Dennis Jacobsen wrote, “I want to take this opportunity to thank you for putting your trust in us over the last 35 years and helping to get us to where we are today. Our people are driven to provide solutions that make your lives and businesses better and easier for you to operate. This commitment is stronger than ever during this exciting time.”

Volaris Group has appointed Erna Hansen to lead the newly acquired company as General Manager. Hansen has been part of the Windward Software team for over 11 years and has been COO for the last 5 years. She is joined by a strong, tenured, and capable senior management team and staff who remain with the company. Windward’s new corporate headquarters will be in Penticton, B.C. Canada, however, some employees will continue to work remotely from the Chicago area.

Under Volaris Group, Windward Software Systems Inc.’s goal is to take its customers to the next level of business management software in the cloud with access to Volaris’ resources and capabilities to build better software solutions and provide additional professional services that add value.


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