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Jennifer Bolster has a diverse work experience in the field of Human Resources. Jennifer started their career as a Benefit Analyst at the National Association of Realtors in 1988. From there, they worked as a Compensation and Benefits Manager at various organizations such as Provena St. Mary's Hospital, Provena Health, Majestic Star Casino, and InteliStaf Healthcare. In 1998, they became a Compensation and Benefits Director at Provena Saint Joseph Medical Center. In 2002, they served as a Compensation and Benefits Manager at Majestic Star Casino. Jennifer then worked as a Human Resources Manager at MED3000 from 2004 to 2011, where they managed day-to-day operations, benefit and payroll administration, and oversaw the compensation and performance review process. Finally, they joined Goodheart-Willcox in 2011 and held positions as Director of Human Resources and Senior Director of Human Resources. In their roles at Goodheart-Willcox, they designed policies and procedures, provided budgetary and strategic planning, and administered long-term human resource strategies.

Jennifer Bolster completed MBA prerequisite courses at the University of Calgary from 1991 to 1992. Prior to that, they earned a BBA degree in Business from Western Illinois University between 1984 and 1986. Jennifer started their higher education by studying Business Administration and Management, General at the University of St. Francis from 1982 to 1984.