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Bobette Wolf has a long history of work experience, beginning in 1985 when they were an Intern for Consumer Products Design at Helene Curtis. Bobette then moved on to Wolf Design in 1987, where they worked as a Designer. In 2006, they founded and became Principal Designer of Malcolm Wolf Inc. Her most recent position is Creative Director at Sail Internet, which they began in 2022.

Bobette Wolf attended the School of the Art Institute of Chicago from 1982 to 1986, where they earned a BFA in Visual Communication. In 1985, they attended the Basel School of Design for Graphic Design.