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Robert McCracken has a diverse work experience in the technology sector. Robert began their career as a Consultant at Transcontinental Direct in 2004, before moving on to become the Chief Information Officer (CIO) at Harte-Hanks, Inc. in 1999. From there, they joined MTI Information Technologies in 2006 as their Chief Technology Officer (CTO). Most recently, Robert served as the Senior Vice President and Chief Technology Officer at Modern Marketing & Commerce, starting in November 2012.

Robert McCracken attended the University of Vermont from 1975 to 1979, where they earned a Bachelor of Science (BS) degree in Bio-Engineering. Later, in 1985 and 1986, they enrolled at the MIT Sloan School of Management for their MBA studies but did not complete a specific degree.