Kevin Schilter

The Architect of Operations

As Chief Operating Officer, Kevin Schilter is responsible for the "big picture" at Windward Software. While the developers build the code and the sales team drives growth, Kevin ensures that the entire engine runs efficiently. He oversees the company’s operational strategy, financial planning, and talent management, ensuring that Windward’s internal processes align with its promise of reliability to customers.

Kevin is not just an executive; he is a cornerstone of the Windward story. His journey with the company spans over 3 decades, giving him an unmatched historical perspective on the software’s evolution. Long-time clients may even recognize him as the original host of Windward Software TV in 2012, where he broke down complex features for users—proof that his leadership is built on deep, hands-on product knowledge.

Following Windward’s acquisition by Volaris Group, Kevin played a critical role in recalibrating the company’s goals. He focuses on sustainable growth, championing data-driven decision-making and long-term financial health.

His leadership philosophy centers on looking beyond individual departments to understand the "whole business." By fostering alignment between engineering, support, and sales, Kevin ensures that Windward remains not just a software provider, but a stable, long-term partner for retailers worldwide.