Cliff Libby, EVP Strategy & Business Development

Matthew Goodman

Cliff Libby, Executive Vice President, Strategy & Business Development for Digital Media Solutions, has more than 20 years of experience dedicated to the performance marketing space. In his role at DMS, Cliff works with other key leaders across DMS to implement the strategic plan to build value through transactions involving key assets. Recognized as an empathetic and effective leader in cross-functional and dynamic environments, Cliff lends his expertise to help execute on current and long-range business plans to grow the value of the organization.

Throughout his dynamic career, including positions at CourseAdvisor, Trilogy Education Services and multiple software and technology service companies, Cliff has become an expert in building high-performing teams, strategic planning and execution, new product and market development and increasing revenue and profit growth.

DMS received a spot on Inc. magazine’s inaugural Best Led Companies list in 2021, recognizing the impact of Cliff alongside fellow DMS leaders.

About the author

Digital Media Solutions

Digital Media Solutions, Inc. (DMS) drives better business results by connecting high-intent consumers with advertisers across our core verticals; Insurance (auto, home, health), Education and Consumer/Ecommerce. Our innovative solutions help consumers shop and save, while helping our advertisers achieve above average return on ad spend. Learn more at