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Cliff Libby

Executive Vice President & General Manager of Education
Digital Media Solutions
Matthew Goodman

Cliff Libby is the Executive Vice President and General Manager of Education at Digital Media Solutions (DMS), the fastest-growing independent digital performance marketing company. In this role, Cliff oversees all lead generation websites, sales operations, affiliate marketing programs and call center activities surrounding the DMS Education division. DMS currently owns and operates domains in the higher education space such as and, which connect with more than one million prospective students each month. DMS helps its clients accelerate growth by deploying diversified and data-driven customer acquisition solutions that deliver scalable, sustainable and measurable marketing results. DMS performance marketing solutions connect the right consumers with the right offers at the right time to achieve the marketing objectives of our clients. DMS is continually innovating to provide new and emerging media and technology solutions that minimize waste and maximize results across the most competitive industries. Since its inception, DMS has demonstrated incredible year-over-year growth which has earned recognition on the Inc. 5000 list in 2014, 2015, 2016, 2017 and 2018.

An accomplished leader in higher education marketing, Cliff comes to DMS with incredible experience in entrepreneurial and high-growth environments. Prior to joining DMS, Cliff held management roles at CourseAdvisor – which was later rebranded to Avenue 100 Media – during its pivotal time as a Washington Post subsidiary. Cliff started his career in admissions at Wheaton College Massachusetts and has since held executive leadership roles in a variety of software and technology service companies focused exclusively in higher education. Cliff graduated with a Bachelor of Arts in American Studies from Wheaton College Massachusetts and earned a Master of Business Administration from Boston University Questrom School of Business. He resides in the Boston, MA area with his wife and children.

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