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Anna Riolo has a range of work experience in various fields. Anna started as a Substitute Teacher at Greenburgh Eleven UFSD in 2008 and worked there until 2013. In 2012, they also worked as a Promotional Specialist for TEAM Enterprises. From 2013 to 2014, they were a Graduate Student Intern at New Life Counseling and Wellness Center. In 2014, they became a Graduate Intern at The Gifford School. Anna then worked as a Membership Consultant at Boston Sports Club from 2013 to 2015. From 2016 to 2018, they served as a Children's Counselor & Advocate at Hope's Door NY. Currently, since 2018, they occupy the position of a Licensed Mental Health Clinician Limited Secure Placement at The Children's Village.

Anna Riolo earned their Bachelor's degree in Psychology from SUNY New Paltz, where they attended from 2008 to 2012. Following this, they pursued a Master's degree in Counseling Psychology in Expressive Arts Therapy at William James College from 2013 to 2015. In addition to their academic qualifications, Anna Riolo has obtained several certifications, including being a Licensed Mental Health Counselor, passing the National Clinical Mental Health Counseling Exam administered by the New York State Education Department in June 2017, and being certified in CPR and AED for Children and Adults in August 2014. Anna also holds a Limited Permit from the New York State Education Department.