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Katelyn Cushman's work experience includes serving as the Associate Director of Alumni Engagement at Bennington College since July 2022. Prior to this role, they worked as a Senior Development Associate at Bennington College from April 2017 to July 2022. Katelyn Cushman - also worked as a Senior Assistant Buyer at The Vermont Country Store from November 2013 to April 2017. Additionally, they worked as an Operations Manager at Drupal Connect from 2010 to 2013, where they specialized in Drupal development, consulting, training, and staffing services for clients including Fortune 500 companies.

Katelyn Cushman attended Flagler College from 2005 to 2009, where they obtained a degree in Business Administration with a focus on Business Administration, Management, and Operations. Katelyn Cushman - later enrolled in Methodist University, although specific details regarding the degree and field of study are unavailable.