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Sean Bailey has a diverse work experience in various industries. Sean started their career as a Recruiter at Aerotek in 2006. From 2008 to 2010, Sean worked as a Sales Representative at Boyer Trucks. Sean then joined Entegee in 2010, where they held multiple roles including Account Manager, Sales Manager, and Branch Manager until 2018. In 2018, they joined The Judge Group as a Director, where they provided clinical workforce solutions in the healthcare sector. Currently, Sean is the Director of Sales at Dahl Consulting since 2021.

Sean Bailey attended Henry Sibley from 1997 to 2001. Sean then went on to study at the University of St. Thomas from 2001 to 2005, where they earned a Bachelor's degree in Finance and Economics.