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Holly Olmstead has a diverse work experience spanning different industries and roles. Their most recent role was as an Educational Consultant at iTutor.com Inc. starting in July 2020. Prior to that, they worked as a Lead Educational Trainer at Strategic Measurement and Evaluation from April 2018 onwards. Holly also has experience as a Substitute Teacher at BUFFALO CITY SCHOOL DISTRICT starting in September 2019 and as a Proctor at the New York State Board of Law Examiners starting in July 2019. Holly is also a Writer for hollyknits.com since June 2010. In the education field, they worked as a Literacy Coach at Sweet Home Schools from June 2013 to June 2015 and as a Teacher at Sweet Home School District from September 1978 to June 2015.

Holly Olmstead obtained a Master's Degree in Educational Leadership and Administration from Niagara University from the years 2007 to 2008. Prior to that, from 1978 to 1980, they pursued a Master of Science in Education specializing in Special Education at Buffalo State University.