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Carolyn Pleiss

Carolyn Pleiss

Senior Vice President & Chief Information Officer

Carolyn Pleiss delivers IT strategy and capabilities applicable enterprise wide. This includes architecture, security and compliance, application development, infrastructure and program management.

With more than 25 years of experience in information technology, Pleiss is a career technologist who has led numerous transformation efforts and managed strategic technology portfolios enabling multimillion-dollar growth.

Most recently, Pleiss was vice president, Strategy and Value Realization.

She first joined Cox AutoTrader Publishing in 2007 before moving to, where she successfully led its agile transformation. In 2015, Pleiss led the Cox Auto Technology integration team as part of the Dealertrack acquisition. As VP, agile delivery, she implemented a product delivery framework that increased the alignment, transparency and consistency of how Cox Automotive performed product planning, prioritization and delivery across the organization.

Prior to Cox Automotive, Pleiss led her own consulting business, where she worked with companies including The New York Times, Boston Globe and others to deliver personalized methodologies and lead enterprise initiatives.

Pleiss is an Agile Certified Professional (ACP) and was named one of the 100 Women Worth Watching by Diversity Journal, as well as a Woman of the Year Honoree by Women in Technology. She currently serves on the board of Literacy Action, the oldest, largest, and leading adult basic education nonprofit in the Southeastern United States.