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Jonathan May has a diverse work experience spanning from being a VP of Innovation and Development at Think Small® to teaching roles in various educational institutions. At Think Small®, they were responsible for the strategic leadership of revenue-generating areas and led analytics and new program development initiatives. Prior to that, they worked as a Director of Innovation at the same organization, focusing on leveraging data-driven insights and scaling programs. Jonathan also served as a Managing Director/Director of Data and Research at Generation Next, where they led data analysis and research for the organization's strategic direction. Jonathan started their career as a Teacher at ST. PIUS V SCHOOL and Commonwealth - Parkville Schools, teaching 7th and 8th grade and 5th and 6th grade respectively. Jonathan also worked as a Graduate Assistant at St. Cloud State University's Department of Economics and as a Reporter at the Caribbean Business Newspaper.

Jonathan May completed a Bachelor of Arts degree in Economics and Education from Hartwick College from 1999 to 2003. Following that, they pursued a Master of Science degree in Applied Economics from St. Cloud State University from 2011 to 2013.