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Tobi Oladapo has a diverse work experience, primarily in the field of technical project management and sales. Starting in August 2019, Tobi worked at Cover as an Inside Sales Representative until September 2021. In September 2021, Tobi transitioned to the role of Senior Sales Representative at the same company, and subsequently became a Technical Project Manager in December 2021. Tobi joined Bamboo Insurance in July 2022 as a Technical Project Manager.

Tobi Oladapo completed their Bachelor's Degree in Accounting and Finance from San Francisco State University, spanning from 2016 to 2019. In addition to their degree, they hold certifications including Certified Scrum Product Owner (CSPO) from Scrum Alliance, obtained in February 2022, and Microsoft Office Specialist Excel 2016 from Microsoft, although the specific month and year of obtaining this certification are not provided.