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Lester A. Wiltfong Jr. has a diverse work experience spanning various roles and industries. Lester A. started their career in 1989 as the General Manager at Northbrook Sports Club. From 2005 to 2019, they worked at Hinshaw & Culbertson LLP, initially as an Office Facilities Coordinator and later as a Legal Support Services Coordinator. In 2009, they became the Editor in Chief and writer for SB Nation's Windy City Gridiron, where they also hosted podcasts. Additionally, Wiltfong worked as a Freelance Writer and Editor, a Photographer/Marketing professional at Serena Vitellaro Photography, and a Litigation Docket Specialist at Foley & Lardner LLP. Lester A. also held roles as a Radio Host at VSporto, a Writer at We Got This Covered, a Writer at The 50 Yard Line, and the Official Chicago Bears Blogger for The Sporting News.

Lester A. Wiltfong Jr. pursued their Bachelor of Fine Arts (B.F.A.) degree in Creative Writing for Entertainment from Full Sail University, from 2017 to 2019. In addition, they acquired several certifications from Lynda.com, including "Lettering Comic Books with Illustrator," "Google Voice Essential Training," "User Experience for Web Designers," "WordPress.com Essential Training," "Green Screen Techniques for Photography and DSLR Video," "Video Production: Location Lighting," "Learning Premiere Pro CC 2015," "Designing Dynamic Layouts with Text and Dialog in Comics," "Blogging for Your Business," "SEO Foundations," "Marketing Foundations," "Building Your Professional Network," and "Learning Personal Branding," obtained between 2017 and 2019.