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Courtney Shepard has a long history of working in the professional field. Courtney started their career in 2006 as a Clinical Case Manager at Hillcrest Educational Centers. In 2007, they moved to Berkshire Works Career Center as a Career Development Counselor. In 2008, they became a Grants Management Specialist at the Department of Career Services. In 2012, they shifted roles to College and Career Navigator at Roxbury Community College. In 2013, they moved to Learning Solutions Winstanley as an Event Coordinator. Currently, they are an Account Manager at Quest Connect, working to grow a small business through the state of MA and all bordering states.

Courtney Shepard attended Union College from 2002 to 2006, where they earned a Bachelor's degree in Psychology.