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Jainie Winter has a diverse work experience starting in 2014 when they worked as a Press and Communications Intern at the Environmental Working Group. During their time there, they assisted in the creation and implementation of public affairs strategies, drafted media reports, and contributed to blog writing.

In 2015, Jainie worked as a Reporting Intern at Kosovalive360, where they pitched and wrote stories, conducted interviews, and published articles. Jainie played a role in influencing public opinion on political issues in Kosovo.

From 2016 to 2017, Jainie worked as an Assistant Publicist at CBH Communications, where they successfully planned and executed events, collected press clippings, and created business plans for new clients.

In 2017, Jainie joined Teak Media + Communication as an Account Executive, where they worked until 2018.

From 2018 to 2020, Jainie worked at EF Education First, initially as a Staff Recruitment Coordinator and later as a North American Staff Recruitment Manager. During their time there, they also served as an Operations Manager in New York, overseeing operations in the region.

Since 2020, Jainie has been working at Elevo Learning, first as an Operations Manager in Southern California, and currently as the Director of Operations in the same region.

Jainie Winter attended Miami University where they pursued a degree in Strategic Communications and Journalism. The specific time frame of their education is unknown. In addition, they obtained a certification in Predictive Index from The Predictive Index in October 2018.