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Caleb Benna has been working in the design field since 2011. Caleb began their career as a Graphic Designer at The Graphic Edge, Inc. in 2011. In 2016, they joined Gannett | USA TODAY NETWORK as a Graphic Designer. From 2018 to 2019, they worked as a Graphic Designer at FIREFLY, Fox Restaurant Concepts, and The James Agency. In 2022, they took on the role of Lead Designer at Ledger Bennett.

Caleb Benna attended Iowa Lakes Community College from 2010 to 2012 and obtained an Associate of Science (A.S.) degree in Graphic Design.