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Dina Osinski began their work experience in 2003 as a Layout Artist at Allen Awards, Inc. In 2006, they became a Designer at SmithCraft Custom Architectural Signs until 2008. From 2008 to 2009, Dina worked as a Graphic Designer at R and R Images, and subsequently as a Graphic Designer at Fox Restaurant Concepts for a brief period. In 2009, they joined IQ Printing as a Graphic Designer until early 2010. From 2010 to 2023, Dina worked as a Creative Director at Sprouts Farmers Market. In 2005, they also started their own design business called Design Details by Dina. Since 2008, Dina has been working as a Graphic Designer/Webmaster at Desert Stages Theatre. Most recently, they have taken on the role of Sr. Creative Director at FoodStory Brands starting in 2023.

Dina Osinski's education history begins in 1998 when they attended LaSalle-Peru Township High School. There, they focused on Basic Skills and Developmental/Remedial Education until finishing in 2001. Following their time at high school, Dina pursued further education at Illinois Central College from 2001 to 2003. Their field of study at the college included both Mechanical Design Techonology and Graphic Design. After completing their studies at Illinois Central College, Dina enrolled in The Art Institutes, where they obtained a Bachelor of Fine Arts (B.F.A.) degree in Graphic Design. Dina attended The Art Institutes from 2003 to 2006.