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Devin Woolery has been working in the professional world since 2008. Devin began their career as a Cashier at Dick's Sporting Goods. In 2009, they took on a Sales Associate/DSD Receiving Associate role at Walmart. In 2010, they started their own company, Devin Woolery Graphics, where they served as the Owner. Devin's duties included generating client brand development and digital marketing strategies, producing website designs, overseeing site development, and providing marketing insight for clients. In 2011, they took on a Student Worship Leader role at Arrow Heights Baptist Church. Since 2014, they have worked as a Graphic Designer & Front End Developer at Thrive15.com - Online Edutainment for Entrepreneurs and Small Business Owners. Most recently, in 2021, they became the Owner of Flow Photos Tulsa.

Devin Woolery attended Broken Arrow High School and Tulsa Community College, where they studied Mathematics, between 2004 and 2006.