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Jefferson Fletcher has a diverse work experience spanning several roles and companies. Jefferson founded and served as CEO of Siimpl since 2016. Prior to that, they co-founded and led BD and customer success at Tag Creative, an award-winning digital experience and product innovation agency from 2008 to 2015. In this role, they worked with various clients such as Microsoft, Starbucks, and Amazon. Prior to their entrepreneurial ventures, Jefferson worked at Microsoft Corporation, where they held several positions including Senior Product Manager and Senior Software Engineer. In these roles, they were responsible for the creation and development of the Internet Explorer Add-Ons Gallery ecosystem and solved UX problems for millions of customers.

Jefferson Fletcher's education history includes studying Political Science at the University of Washington. The information does not specify the start or end year of their time at the university, nor does it mention whether they obtained a degree in the field of study.