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Rosalind B. has a long history of work experience, beginning with their military service in the US Army from 2006 to 2009. Rosalind then worked as an Operating Room Technician at Scripps Green Hospital and UMass Memorial Medical Center - University Campus from 2008 to 2013. In 2013, they joined Brigham and Women's Hospital as a Product Development Specialist at TJX from 2014 to 2021. Most recently, they have been a Staff Accountant at RapidMiner and a Payroll Specialist at Veterans Inc. since 2021. Rosalind is currently employed as a Corporate Accountant at Putnam Investments.

Rosalind B. earned a Bachelor of Science in Accounting and Finance from Framingham State University.