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Jordan Stephen has a diverse work experience spanning over several decades. Jordan started as a Cabinet Maker at Architectural Components & Materials Inc in 1986, where they were involved in the design, assembly, and production of custom laminated cabinets. Jordan then worked as a Machinist/Production Worker at Modern Machine Shop from 1988 to 1991. In 1994, they became a Technology Education Teacher at Naperville School District 203, teaching technology to students. From 1995 to 1996, they worked as a Technology Educator at Madison Jr. High School & Kennedy Middle School, teaching technology to 6th - 8th grade students. Jordan continued their career in education as a Technology Education Teacher at East Prairie School from 1996 to 2002, where they developed and implemented a state-of-the-art Technology Education curriculum center. During their time at East Prairie School, they also held the position of Director of Technology, overseeing the development of technology-based curriculum, staff training programs, and the operations of all technology-related equipment and materials. In 2000, they became the Technology Director at OSX Users Group, where they served until 2010. Jordan also served as Co-Chair of Illinois Computing Educators from 2000 to 2007. Jordan's most recent role is as the Technology Director at Lincolnwood School District 74, starting in 2021.

Jordan Stephen has an extensive education history. From 1988 to 1991, they attended Danville Area Community College where they obtained an Associate of Arts degree. Following this, from 1991 to 1994, they pursued a Bachelor of Arts degree in Industrial Technology Education at Illinois State University. In addition, during the same period, they also obtained a Bachelors degree in Industrial Technology Education from Illinois State University.

Continuing their educational journey, from 1995 to 1997, Jordan attended National Louis University and earned a Masters Degree in Curriculum And Instruction. Jordan further pursued their studies at National Louis University from 1998 to 2000, acquiring an additional Masters degree in Curriculum And Instruction.

Later on, from 2006 to 2009, they attended Concordia University and obtained a Masters degree in Educational Leadership With Type 75 Administration. Additionally, in 2007 to 2008, Jordan studied at Concordia University Chicago and achieved a Masters degree in Instructional Leadership with Type 75 certification. Overall, Jordan Stephen has a strong educational background in various fields related to education and instructional leadership.