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Jim Dailey has over 10 years of work experience in various roles. Jim started their career in 2011 at The Home for Little Wanderers, where they worked as a Direct Care Counselor, Teacher, Supervisor, and eventually as the Director of Milieu. In 2017, they joined The Hollister Group as a Recruiting Manager for Accounting & Finance, and later became the Senior Manager in the same department. Jim's role at The Hollister Group focuses on delivering a consistent experience of excellence and building long-term relationships with clients and talent.

Jim Dailey attended Xaverian Brothers High School from 2002 to 2006. After completing high school, they went on to the University of Massachusetts Amherst from 2006 to 2010. At UMass Amherst, they pursued a Bachelor of Science degree with a major in Psychology and a minor in Education.