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Alaina Liberto's work experience includes serving as the Chief Information Officer at Chesapeake Employers' Insurance Company since October 2018 and as the Director of Project Office since August 2011. Prior to that, they worked as a Manager at Sogeti from January 2001 to August 2011.

Alaina Liberto holds a Bachelor of Science (BS) degree in Information Systems from the University of Maryland Baltimore County, which they completed from 1996 to 2000. In addition, they pursued a Master of Business Administration (MBA) in Finance at Loyola University Maryland, from 2004 to 2008. Alaina also has a certification in Project Management (PMP) from the Project Management Institute. The specific month and year of obtaining the certification are not provided.