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Robby Oakes began their work experience in 2001 as a Financial Planner at Northwestern Mutual Financial Network. Robby then became the Managing Director at Corporate Investors Mortgage Group in 2003.

Robby Oakes attended Chapel Hill High School from 1994 to 1997. Following this, from 1999 to 2002, they pursued a Bachelor of Science (BS) degree in History and Political Science at the University of North Carolina at Chapel Hill.