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Kaitlyn Bennett has an extensive work experience in various roles and industries. Kaitlyn began their career at Jefferies in 2008, where they worked as an Assistant Vice President for almost a decade. In 2017, they joined Farmer's Fridge as a Senior Manager in the Legal and Compliance department. After four years at Farmer's Fridge, they transitioned to November Project, Inc., where they served as a Co-Leader, focusing on connecting the Chicago community through free fitness. In 2021, Kaitlyn joined AJ Capital Partners as the Director of Risk Management. Kaitlyn quickly progressed to the role of Vice President before assuming their current position as the Chief Compliance Officer and Head of Risk Management.

Kaitlyn Bennett attended Chelsea High School from 1997 to 2001. Kaitlyn then enrolled at Shenandoah University from 2001 to 2005, where they earned a Bachelor of Fine Arts (BFA) degree. During their time at Shenandoah University, they studied dance and mathematics. In 2010, Kaitlyn obtained a Postbaccalaureate Certificate in Paralegal Studies from Kaplan University. The exact month of the certification is not provided.