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Jeff Squires has a diverse work experience spanning several companies and roles. Jeff first worked as a Teacher/Guidance Counselor at Oregon City Schools from 1979 to 1985. Jeff then became the Principal at Fairbanks Local Schools from 1985 to 1991. In 1991, they joined McGraw-Hill Education as a Sales Consultant for a brief period. From 1992 to 1994, Jeff worked at The Psychological Corporation. Jeff then joined Houghton Mifflin Harcourt and held various positions, including Regional Vice President of Sales from 1994 to 2013 and General Manager from 1995 to 2019. In 2020, they joined Riverside Insights as a Senior Sales Director, a role they currently hold. Before, Jeff was the Director of Sales at Houghton Mifflin Harcourt.

Jeff Squires has a significant education background. Jeff first attended The University of Toledo from 1975 to 1979, where they obtained a Bachelor's degree in Education. Jeff later pursued a Master's degree at the same institution from 1980 to 1981, specializing in Secondary School Administration/Principalship. After a brief break, Jeff returned to The University of Toledo from 1983 to 1985 to complete another Master's degree, this time in Counselor Education/School Counseling and Guidance Services. Lastly, they attended Ashland University from 1989 to 1991, where they obtained a Certification in Superintendency and Educational System Administration.