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Chrissy Oswald has worked in a variety of roles since 2002. Chrissy began their career as an Office Communications Manager at GM Powertrain, where they served as a Communication Liaison between Engineering/Managerial staff and 450 plant union employees, as well as being the Chief Editor and designer of the GM bi-monthly newsletter - @Baltimore. In 2005, they moved to The Cathedral Foundation, where they served as the Graphic Design/Production Supervisor, overseeing staff for the on-going production projects for the Catholic Review, as well as leading quality control for all tasks associated with the Cathedral Press & Catholic Printing Services. In 2010, they began working as a Patient Registrar & Insurance Specialist at MedStar Good Samaritan Hospital. In 2016, they joined Acosta Sales & Marketing Foodservice as a Sales Merchandiser, responsible for incremental sales, distribution, new items, on shelf availability, and product integrity for 140 accounts across Maryland/Delaware. Since 2018, they have been employed at GiGstreem, where they serve as a Residential Sales Manager and Sales Consultant, delivering the internet solution of the future over dedicated multi gigabit connections.

Chrissy Oswald has a BS degree in Computers: Liberal Arts from Villa Julie College, which they obtained from 1996 to 1999. Before that, they attended Institute of Notre Dame High School from 1991 to 1995, where they studied Computers. Chrissy also has certifications in Blockchain Basics and Smart Cities: Solving Urban Problems Using Technology, both obtained from LinkedIn in January 2020.