EMCEE / KEYNOTES
Erwin A. Riley IV Program Manager of Content & Delivery, Work Ready Oklahoma Erwin A. Riley IV is the Program Manager of Content & Delivery at Work Ready Oklahoma. A proud New Orleans native, retired IT professional, and U.S. Air Force veteran, Erwin IV brings creativity, clarity, and energy to distance learning statewide. He’s skilled in frameworks like Motivational Interviewing, Crucial Conversations, and Family-Centered Coaching. Outside the virtual classroom, Erwin IV is a professional wrestler—bringing that same crowd-ready presence, rhythm, and storytelling to help people level up in work and life.
Bailey Siber Chief of Staff to the Mayor, City of Oklahoma City
Bailey Siber is Chief of Staff to the Mayor of Oklahoma City. She previously served as Deputy Chief of Staff to the Mayor and as Senior Program Manager in the Office of Innovation, where she led initiatives ranging from data governance to homelessness. Before joining the City of Oklahoma City, she worked for the City of Boston’s civic innovation and design team, MONUM. Siber previously held roles in nonprofits and tech startups focused on improving health outcomes and advancing economic mobility. Siber graduated from the Harvard Kennedy School with a Master of Public Policy and a certificate in Management, Leadership, and Decision Sciences. She earned her bachelor’s degree, summa cum laude, from Tufts University.
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