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Craig Dickman has a diverse work experience spanning multiple industries. Craig began their career as an Administrative Intern at Memorial Hospital of Tampa in 2004. Craig then worked as a Project Intern at Cayuga Medical Center and Lifelong in 2005. In the same year, they also served as an Insurance Agent at American Income Life Insurance Company. In 2006, they worked as a Physician Scheduler at South Denver Anesthesiologists and later as an ED Registrar at Memorial Hospital of Tampa. From 2008 to 2016, Craig served in various roles within the United States Army, including Physical Evaluation Board Liaison Officer, Assistant to the Company Commander, HIPAA Privacy Officer, and Cadet Waivers Administrator. In 2016, they joined Catskill Regional Medical Center as a Cancer Service Program Outreach Coordinator and later worked as a Clinical Transformation Analyst at Bon Secours Charity Health System. Craig currently holds the role of Director of Population Health at Bon Secours Health System.

Craig Dickman holds a Master of Business Administration (MBA) degree in Health/Health Care Administration/Management, which they obtained from the State University of New York at Oswego from 2018 to 2021. Craig also pursued Lean Six Sigma studies at Purdue University from 2018 to 2019. In 2005, they earned a Bachelor's degree in Health Policy from Ithaca College. Additionally, they have received certifications in Caboodle, Epic Ambulatory, Radar Administrator, and Reporting Workbench Administrator from Epic in 2016.