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Kenny Riley has a diverse work experience in the education technology industry. Kenny started their career in 2008 as an Educator at Resurrection Catholic School, where they worked until 2011. In 2012, they joined Frontline Technologies as a Client Services: Implementation & Support specialist and later became an Implementation Team Leader, leading a team and improving implementation processes. From 2016, Kenny worked at Frontline Education, initially as an Implementation Manager for Frontline Central and later as an Education Solution Executive. Currently, they hold the position of Regional Sales Director, leading a sales team and collaborating with K12 communities in the Mid-Atlantic region.

Kenny Riley holds a Master of Science degree in Physical Education Teaching and Coaching from West Virginia University. Kenny also completed a Master of Science degree in Athletic Coaching Education from the same university between 2008 and 2010. In addition, they obtained a Pennsylvania Teaching Certificate K-12 in Health and Physical Education/Fitness from Eastern University in 2010. Kenny's undergraduate education includes a Bachelor of Science degree in Sports Management from Eastern Mennonite University, which they completed from 2004 to 2007.