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Jessica Hearn has held a variety of roles in their career. Jessica began their professional experience in 2003 as an Office Assistant at Minnesota Medical. In 2009, they held roles as a Web Moderator at Star Tribune, a Literary Intern at Mendel Media Group, a Web Developer, Copyeditor, and Designer as a freelancer, and an Office Assistant at Minnesota Medical. Jessica then worked at CaptionMax as a Transcriber in 2013. From 2014 to 2019, they worked at Nerdery as a Software Engineer, Team Lead, Senior Software Engineer, and Engineering Manager. In 2019, they joined evopark GmbH as an IT Director and Senior Full-Stack Developer & Product Owner. Her most recent role is Engineering Lead, Integrations at ChartMogul, which they began in 2022.

Jessica Hearn completed their high school education at Wayzata High School from 2001 to 2005. Jessica then went on to earn a Bachelor's Degree in Musical Theatre and Creative Writing from New York University from 2005 to 2009. In 2009, they also obtained a Professional Certificate in Book Publishing from New York University's School of Continuing and Professional Studies. In 2011, Jessica Hearn completed a Professional Certificate in Interactive Design and Marketing from the Minneapolis College of Art and Design, which they completed in 2014. In November 2018, Jessica Hearn obtained the PSM I certification from Scrum.org.