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Olivia Shapiro has a diverse work experience, beginning with a Product Intern and Database Assistant role at The Grommet in 2012. In 2015, they became an Administrative Intern for the Investment Team at Acadian Asset Management. In 2016, they were a Marketing Associate at Accomplice VC. In 2017, they were a Client Relationship Representative at IBM, where they conducted an 8-week research project to develop strategies for effectively integrating Watson Artificial Intelligence technology into IBM's technical support. In 2018, they were an Enterprise Account Executive at IBM and was also selected as a trainee in the IBM Global Sales School (Summit Program). During the program, they received training in mock sales calls, technology boot camps, driving technical demos, presentations, negotiations and demonstrating selling skills to senior sales executives. Olivia was awarded 1st place out of 60 participants in the final mock client presentation. In 2021, they were a Manager of Mid-Market Sales and an Account Executive at Apiiro. Finally, in 2022, they became a Member at Pavilion.

Olivia Shapiro completed their Bachelor's degree in Cognitive Science: Decision and Cognition Track from the University of Michigan. Prior to that, they attended Lexington High School. In addition, they obtained a certification from IBM's Global Sales School in March 2019.