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Drew Stein has extensive work experience in various roles. In 2010, they worked at Detroit Switch Inc. as a Process Improvement / Operations leader, where they implemented an ERP system to enhance manufacturing efficiency and achieve organizational goals. From 2015 to 2016, they served on the board of directors for DSR. In 2017, Drew joined Deltek as an Agency Business Consultant, collaborating with clients and partners to align software integration with business needs. At the same time, they were an active member of the board of directors for SMC Business Councils, providing insight and support for small businesses, manufacturers, and non-profits. In 2020, they joined TEKsystems as a Continuous Improvement Consultant before transitioning to Premier Consulting & Integration LLC as a Senior Consultant in September of the same year.

Drew Stein obtained a Master of Business Administration (M.B.A.) degree with a focus in Marketing from Geneva College, where they studied from 2010 to 2012. Prior to that, they completed their Bachelor's Degree in Marketing and Management as a dual major at Slippery Rock University of Pennsylvania from 2006 to 2010.

In addition to their formal education, Drew Stein has achieved several certifications. Drew passed the WorkBook Core Certification Exam at Deltek in April 2022. In June 2020, they obtained a Project Management Professional (PMP) certification from the Project Management Institute. Drew has also achieved the Six Sigma Black Belt certification from Aveta Business Institute, although the specific month and year of its attainment were not provided.