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Jack Calhoun began their work experience in 1986 as a Sales Representative at Cintas Corporation, where they exceeded sales targets. Jack then joined William C. Brown Publisher (now part of McGraw-Hill) in 1987 and served as a Sales Representative responsible for territory sales and product training. In 1989, they became a Senior Marketing Manager at the same company, overseeing marketing operations and participating in strategic planning. From 1992 to 1993, Calhoun served as Vice President of Sales & Marketing at William C. Brown Publishers, managing all sales and marketing activities. Jack joined Cengage Learning in 1993 and held various roles, including Product Manager, Vice President - Team Director, Vice President - Product Director, and Senior Vice President - Global Product Management. During their time at Cengage Learning, they led product development, acquisitions, and integration efforts, resulting in significant revenue growth. In 2014, Calhoun launched and served as President of NewKnowledge United, a successful learning services and solutions company, until its sale in 2017. Jack then became the Managing Director at NewKnowledge United / TiER1 Performance, where they directed business development efforts and maximized revenue potential. Afterward, Calhoun joined McGraw-Hill Education as the Vice President of Product Portfolio from 2018 to 2019. Currently, they hold the position of Vice President, Publisher/Editorial Director at Goodheart-Willcox since 2020.

Jack Calhoun received their Bachelor of Science degree in Business Administration/Marketing from Miami University in 1986.