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Drew Stricker began their work experience in 2002 as a High School Teacher at Chicago Public Schools, where they served until 2016. In 2016, they joined OneGoal as the Director of Teacher Support for Years 1 & 2. Drew later transitioned to the role of Senior Director of Data and Learning at OneGoal, where they are responsible for setting and executing the vision and direction of program learning in Chicago.

Drew Stricker received their Bachelor's degree in English/Language Arts Teacher Education from Miami University in 2002. Prior to that, they attended Trotwood-Madison High School from 1993 to 1997. Drew later pursued a Master's degree in Mathematics Teacher Education and graduated from DePaul University in 2006.