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Anna Rawlings has extensive work experience in the legal field. Anna started their career as an Associate at Ropes & Gray LLP in 2007 and worked there until 2010. Anna then joined Boston Children's Hospital as an Associate General Counsel from 2010 to 2015. After that, they worked as Counsel and Senior Associate at Davis Wright Tremaine LLP from 2015 to 2017. Anna then moved to LifeCenter Northwest, where they held the positions of Vice President and General Counsel from 2017 to 2019, and later became the General Counsel and Vice President Administration.

Anna Rawlings obtained their Bachelor of Arts degree in Psychology, with a Pre-Medicine focus, from Whitman College. Anna attended Whitman College from 1999 to 2003. Following their undergraduate studies, Anna pursued a Juris Doctor (JD) degree from Harvard Law School. Their time at Harvard Law School spanned from 2004 to 2007.