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Randi Weiss has a diverse work experience spanning over two decades. Randi began their career in 1995 as a Program Manager in Marketing for the National Association of Secondary School Principals/Student Councils. Randi then worked as a Media Relations Specialist at Road Runner from 1999 to 2000. In 2001, they joined Williams Mullen as a Senior Marketing and Business Development Manager, where they stayed until 2010. During their time at Williams Mullen, they played a significant role in developing marketing and business strategies. In 2010, they moved to Arnold & Porter Kaye Scholer LLP, where they held the positions of Senior Business Development Manager until 2016, and then Director of Business Development from 2017 onwards.

Randi Weiss obtained a Bachelor of Arts degree in Psychology from Lafayette College, where they attended from 1984 to 1988. Randi then pursued their Master's in Business Administration with a focus on Marketing at The George Washington University from 1991 to 1994.