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Jessie Headrick has a diverse work experience that spans from 2015 to 2022. Jessie began their career at Adobe as a Campus Representitive in 2015. Jessie then worked at Informatics Design Studio as a UI/UX Designer. In 2016, they worked as a UX Design Intern at R/GA and a Web Design Teaching Assistant at CMU School of Design. In 2017, they were an Service and Interaction Design Intern at Fjord. In 2018, they worked at Palantir Technologies as a Product Designer and at NAVER Corp as a UX Design Intern. Jessie is currently the Head of Design at Candid Health since 2022.

Jessie Headrick attended Carnegie Mellon University from 2014 to 2018, where they earned a degree in Visual and Experience Design with a focus on Design.