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Tommy Grappin's work experience begins in 2006 at Radisson, where they worked as a Banquet Captain, providing high-level service and leading teams for events. Tommy then joined the YMCA of Middle Tennessee as a Wellness Consultant from an unspecified start date until 2014. In 2010, they became a Teacher Leader at Metro Nashville Public Schools, where they directed and coordinated teachers, developed curriculum, and provided professional development. From 2012 to 2017, Tommy worked as a Learning Content and Technology Consultant at Pearson, specializing in outside sales and providing learning solutions for higher education instructors. Tommy then moved to Remind and held multiple sales roles, including Account Executive, Senior Account Executive, and Regional Sales Manager, from 2019 to 2021. In 2021, they joined RingCentral as an Enterprise Sales Executive focusing on the education sector, and in 2022, they became the Director of Inside Sales at Quizizz.

Tommy Grappin's education history includes completing a Master's of Instructional Leadership from Cumberland University in the field of Instructional leadership. This was achieved from 2015 to 2016. Prior to that, they obtained a Bachelor's of Science in Health and Physical Education/Fitness from Western Michigan University, which they completed from 2006 to 2010. In addition to their formal education, Tommy Grappin has also obtained several certifications. These include the Pearson Applied Selling Skills (PASS) certification from Pearson, which was obtained in November 2018, and the Leadership: KNOWLEDGE Level 1 certification from Pearson College and Career Readiness Programs, which was obtained in October 2018. Tommy also obtained the Basic Professionalism certification from Pearson College and Career Readiness Programs in November 2017.