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Bobbie Jeske has a diverse work experience in the IT industry. They began their career at Pace Membership Wearhouse in 1989 as an IT test administrator, where they held several positions before the company closed down. Their responsibilities included data entry with a high typing speed of 12,000+ keystrokes per hour and assisting the accounting department with invoice entry. In 1994, Bobbie joined Pulte Mortgage as the Director of Service Delivery IT Support. They later transitioned to the role of Director of Service Delivery IT in 2001. The exact end dates for both roles at Pulte Mortgage are not provided.

Bobbie Jeske attended Parks College from 1982 to 1984, although the specific degree and field of study are not provided.