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Rebecca MacGregor has over 20 years of work experience in various marketing and program management roles. From 2004 to 2006, they worked as a Program Coordinator at Applied Proactive Solutions. Rebecca then joined Junior Achievement of Western MA, Inc. in 2006 as a Program Manager, where they stayed until 2011. In 2011, they joined Holyoke Medical Center as a Marketing & Development Supervisor before being promoted to Director of Marketing in 2014. Currently, they are serving as the Executive Director of Marketing & Community Relations at Holyoke Medical Center.

Rebecca MacGregor received their BA in Business Management from the Isenberg School of Management, UMass Amherst in 2000. Rebecca later pursued a Master of Business Administration (MBA) from the same institution, graduating in 2019.