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Chandra Osterhaus has been working in a variety of roles since 2005. Chandra began their career as a Product Communications Coordinator at Atwood Publishing. In 2008, they moved to WPS Health Insurance where they worked as a CSR. In 2013, they joined Wagner Insurance and Financial as an Agent and is currently working as a Sales Development Representative at Avid Ratings.

Chandra Osterhaus attended Madison Area Technical College from 2002 to 2005.