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Rob Pittsley has a diverse work experience spanning from 1999 to 2017. Rob began their career as a Sales/Technician at Staples, where they excelled in computer sales, diagnosis, repair, and upgrading. After that, they joined Pittsley Realty as an Office Assistant, where they standardized computer processes and created their website. Rob then worked at Best Buy as part of the Geek Squad, demonstrating their technical expertise and problem-solving skills. Rob gained experience in the field of data analysis at LTM Inc., specifically in supply chain management for the Department of Defense. As a DJ at AAA Mobile DJs, Rob developed valuable skills in public speaking and entertainment. Rob later transitioned to Telenetwork as a Technical Support representative, providing DSL internet service support and exhibiting strong customer service skills. From 2010 to 2017, Rob worked as a freelancer, offering their expertise in audio engineering, web design, and computer repair. Most recently, they were employed at Derive Systems as an Efficiency Calibration Engineer, where they developed vehicle calibrations to enhance efficiency and reduce fuel usage. Rob also managed product deployment and acted as the primary engineering contact for technical support. Throughout their career, Rob has demonstrated strong technical skills, excellent customer service, and the ability to adapt to various roles and responsibilities.

Rob Pittsley attended Polo Community High School from 1995 to 1999, obtaining a High School diploma. Afterward, they enrolled in Sauk Valley Community College from 1999 to 2001. While the information does not specify if they completed a degree at Sauk Valley, it can be inferred that they pursued some form of higher education during this time. Finally, Rob Pittsley attended Columbia College from 2004 to 2006, where they obtained a Bachelor of Science (BS) degree in Business Administration.