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Christopher Bailly has worked for five different companies in various roles since 2007. Christopher began their career at WIN Interactive, Inc. as a Litigation Consultant in 2007. In 2012, they joined Sun Life Financial as an Applications Developer Analyst and was promoted to Senior Applications Developer Analyst the same year. In 2013, they moved to Delaware Life (formerly Sun Life) and continued in the same role. In 2015, they switched to Next Generation Insurance as a Software Engineer. Finally, in 2016, they joined GradGuard - College Life Protected as a Lead Engineer, and was later promoted to Director of Technology and then Chief Technology Officer.

Christopher Bailly attended Northeastern University School of Law from 2004 to 2007, where they obtained a Juris Doctor (J.D.). Prior to that, they attended New York University from 1999 to 2003, where they received a Bachelor's Degree in Music.