Before joining Cuesta, Dylan led large, customer-facing digital transformation programs. He also founded multiple software and e-commerce companies in addition to a yoga studio, giving him hands-on entrepreneurial experience. He led global IT and digital marketing transformation for a Fortune 100 healthcare and medical device company, with a focus on AI and data protection in a highly regulated environment. He oversaw product management, operations, and delivery for a 300-person team supporting more than 500 digital properties including B2B and B2C e-commerce sales. He also spent seven years in Germany leading international expansion for one of the country’s largest retailers, helping grow its B2C digital business grow over 600%. Dylan is an advisory board member of the non-profit standards organization, MACH Alliance, which provides a framework to enterprise leaders to capture value faster from their software investments, specifically in customer-facing data and AI.
Dylan joined Cuesta to share his experience with executives and management teams, helping them use technology to better serve customers and rethink how they work. He is passionate about uncovering creative opportunities that organizations may not yet realize are possible.
Dylan lives in Lake Bluff, Illinois, with his wife, three children, and their doodle. In his free time, he plays guitar, soccer, hockey, and paints ski resorts. On school breaks, he enjoys sailing, paddling, surfing, and skiing.