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Kaitlyn Bieszk began their career in 2011 as a Teacher at the Howard-Suamico School District. In 2017, they were promoted to Head of Department and held this position until the present. In 2018, they also worked as a Teacher at VIPKid, where they executed English curriculum for students learning the language. Kaitlyn generated and retained clients while maintaining a flexible schedule and provided weekly progress reports for over 100 clients. Kaitlyn worked at VIPKid until 2019.

Kaitlyn Bieszk began their education at the University of Wisconsin-Stevens Point in 2006, where they pursued a Bachelor of Science degree in Teacher Education and Professional Development, with a focus on specific subject areas. Kaitlyn successfully completed their degree in 2011 and also obtained a Teacher License from the University of Wisconsin-Stevens Point in May 2011.

Following their undergraduate studies, Kaitlyn Bieszk enrolled in Silver Lake College and pursued a Master of Arts degree, which they completed in 2014. However, the field of study for their master's degree is not provided.

In terms of additional certifications, Kaitlyn Bieszk obtained the Edpuzzle Coach certification from Edpuzzle in February 2019. Additionally, they obtained a Teacher License from the University of Wisconsin-Stevens Point in May 2011, further enhancing their qualifications in the field of education.