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Cydney Whitehead started their work experience in 2013 as a Restaurant Manager at Flying Squirrel Pizza Co. Cydney held this role until 2017. From 2017 to 2020, they worked as an Account Manager at Willie's Reserve. In 2020, they joined Green Revolution as a Regional Account Manager and stayed with the company until 2022. Currently, Cydney is working as a General Manager at Locust Cider, starting in May 2022.

Cydney Whitehead began their education at Seattle Central College, where they attended from 2011 to 2012. However, there is no information available regarding the degree or field of study they pursued during this time. Later on, from 2018 to 2021, Cydney enrolled at the Community Colleges of Spokane, where they obtained an Associate of Arts (AA) degree. Cydney specialized in Professional, Technical, Business, and Scientific Writing while studying at this institution.