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Jen Canole has extensive work experience in the field of development and external relations in the arts industry. Jen started their career at Actors Theatre of Louisville in 1999 as a Literary Intern, where they collaborated with acting apprentices, researched and wrote articles, and developed study guide materials. In 2000, they joined Trinity Repertory Company as a Public Relations Intern, where they wrote press releases, articles, and bios, pitched stories to the media, and investigated publicity opportunities. Over the years, they held various roles within Trinity Repertory Company, including Grants Writer, Assistant Director of Development, Associate Director of Development, and Associate Director of External Relations. In 2016, they became the Director of Development at Trinity Repertory Company, and later served as the Interim Director of Development and Interim Executive Director. Jen'swork at Trinity Repertory Company involved strategic development planning, institutional giving, and overseeing external relations.

Jen Canole attended Amherst Central High School from 1991 to 1995. Following their high school education, they attended Ithaca College from 1995 to 1999, where they earned a Bachelor of Arts (BA) degree in English.