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Jennifer Drago began their professional career in 2009 as a Print and Lab Monitor for Westphal Design & Imaging. In 2010, they took on a Graphic Design Co-Op position at Duane Morris, LLP, as well as a Graphic Designer role for Drexel Campus Activities Board. Jennifer also served as Vice President and Designer for the student-run Drexel Graphics Group. In the same year, they began Freelance Graphic Design Services and a Senior Designer role at Sides Media. In 2015, they became a Lead Designer at fyra, primarily focused on modernizing a suite of sites for a healthcare publication company. In this role, Jennifer provided visual design, UI, and UX for new sites, redesigns, maintenance of existing sites, and marketing pieces including email, social, and print. Jennifer also oversaw adherence to branding and design standards.

Jennifer Drago attended Holy Name High School from 2003 to 2007. Jennifer then attended Drexel University from 2007 to 2011, graduating with a Bachelor of Science in Graphic Design and Web.