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Ann Lennart began their work experience in 2006 at Lifetouch National School Studios, where they served as a Studio Manager/Photographer at Prestige Portraits until 2011. In 2011, they joined The Pabst Theater Group and held the positions of Director of Private Events and Private Events Coordinator.

Ann Lennart obtained their Bachelor of Fine Arts (BFA) degree from the University of Wisconsin-Milwaukee, where they studied from 2003 to 2007.