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Ann Reilly has a diverse work experience spanning from 2005 to the present. Ann started their career as a Counselor at Haven Youth and Family Services in 2005 and worked until 2007. In 2011, they began working as a Yoga Instructor at Core Power Yoga and held the position until 2016. From 2016 to 2020, Ann worked as a Bookkeeper at Find Your Balance Bookkeeping. In 2018, they joined New City Property Management LLC as the Director of Operations, where they worked until 2020. From 2020 to 2021, Ann served as an Investment Portfolio Manager at Westward 360. Currently, they hold the position of Vice President of Rental Management at Westward360.

Ann Reilly attended Northwestern University from 2001 to 2005, where they obtained a Bachelor of Science degree in Psychology.