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Courtney Head started their work experience in 2005 as a Human Resources Assistant at Main Street Bank & Trust. From there, they joined Hendrick Health in 2007 as a Recruiter, and later served as the Benefits Manager. Courtney then progressed to become the Director of Human Resources, and eventually became the System Assistant Vice President of Human Resources. Currently, they hold the position of Hendrick Health Vice President, Human Resources.

Courtney Head has a Master's degree in Human Resources and Industrial Relations, which was obtained from the University of Illinois Urbana-Champaign in 2003. Prior to that, they earned a Bachelor of Science degree in General Studies from Texas Tech University, completing their studies in 2000. In addition to their formal education, Courtney Head holds certifications such as Certified Employee Benefits Specialist from the International Foundation of Employee Benefit Plans (IFEBP) obtained in September 2017, and Senior Professional in Human Resources from the Human Resources Certification Institute obtained in October 2015. Courtney also has a SHRM Certified Professional certification, although the specific details regarding its awarding are unavailable.