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Winter Calkins' work experience includes roles in various industries and positions. In 2022, Winter worked as an Engineering Project Manager II at Deeplocal, where they were responsible for creating interactive experiences. From 2017 to 2022, Winter served as a Project Director at Spectacle, overseeing project management and design. They also worked as an Escape Room Puzzle Designer at Time to Escape Denver from 2017 to 2019. Prior to that, Winter worked as a 3D Imager and Processor at ZELUS in 2016. They also served as an Art Coordinator at Shine Shed from 2012 to 2015, where they designed and built community art installations. Winter's experience also includes working as an Education Manager at Orlando Science Center from 2012 to 2015, a Specialist Mobile Device Technician at Apple from 2011 to 2012, and a Program Coordinator at Florida Atlantic University from 2006 to 2011.

Winter Calkins obtained a Bachelor of Arts (B.A.) degree in Anthropology from the University of Central Florida, where they attended from 2006 to 2010. They later pursued a field of study in Electrical Engineering at Arizona State University from 2017 to 2018, although the information does not specify if they obtained a degree in this field.