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Matt Leonard has a diverse work experience spanning various roles and industries. Matt worked as a Social Studies Teacher at Loyola Academy of Saint Louis from August 2006 to July 2010. Matt then worked as a Lecturer at San Francisco State University from January 2012 to August 2013, and later as a Clinic Coordinator from May 2013 to December 2013. In 2014, they worked as a Consultant at The Gatesworth for a year. In 2015, they joined Sherpa CRM as a Client Onboarding Specialist and Trainer, and later held the positions of Client Onboarding Manager, Director of Customer Onboarding, and currently serves as the Director of Customer Experience and Onboarding since March 2019.

Matt Leonard obtained their Bachelor of Arts in Psychology from Washington University in St. Louis in the years 2004 to 2006. Matt then pursued a Master of Science in Clinical Psychology at San Francisco State University from 2010 to 2012. Prior to these degrees, they attended Northwestern University in 2002 and 2003, although the specific field of study and degree obtained during that time are unknown.