Mr. Fleming has over thirty years of professional business experience, representing some of the Most Admired Companies in the world. He is an Author, Founder, and President of The Sphinx Club®, Make America Hope Again®, and Fleming Consulting LLC®. He has deep executive experience in leadership roles as the Chief Information Technology Officer at Chicago Public Schools, Vice President of Global Business Transformation at McCormick & Co., Senior Director of Enterprise IT Project & Portfolio Management at Aon Service Corporation, Senior Director of Enterprise Business Solutions at Molson Coors Beverage Co; MillerCoors USA, Senior Director of IT Client Relationship Management at Astellas Pharma, Global Program Integration & Management (PMO) Manager at Deloitte Consulting, Global IT Manager at Merck & Co., Business Systems Manager at Philip Morris-Kraft Foods Company, Director of Client Services at The New York Times Company, and held various leadership positions at the Chicago Tribune Company.

He is a recipient of the 2025 Chicago Public Schools, Chief Innovation Officer Award, 2025 Council of the Great City Schools (CGCS) CIO Distinguished Service Award, 2025 IT Senior Management Forum Technology Executive of the Year, Education, 2025 & 2024 ChicagoCIO ORBIE CIO of the Year Awards Finalist, Non-Profit/Public Sector, Large Enterprise (193 Nominees), 2024 The District Administration Top 100 Influencers in Education, 2024 National BDPA Technology Excellence Award, 2024 & 2023 SIM Chicago CIO of The Year Awards Nominee, 2022 Crain’s Chicago Business Notable Black Leaders and Executives, 2022 Chicago Defender Men of Excellence, 2022 Global Diversity & Leadership Conference’s Top 100 Global Leaders Award, 2020 Albert Nelson Marquis Lifetime Achievement Award in Science & Engineering, 2014 Outstanding MBA of the Year for the National Black MBA Association, 2014 DiversityMBA Magazine’s Top 100 Executives Under 50 Achievement Award recipient, 2014 DeVry University’s Distinguished MBA Alumni Achievement Award recipient, 2013 National BDPA Epsilon Professional Achievement and Corporate Champion Award recipient, and recognized by the International Who’s Who in Professional Management in 2000.

Mr. Fleming is member of the Oracle Customer Advisory Board, Microsoft Customer Advisory Board, InspireCIO Leadership Network (ChicagoCIO), Accenture SAP Leadership Council, Gartner CIO Forum, National Forum of Black Public Administrators, a lifetime member of the National Black MBA Association, a member of the IT Senior Management Forum, a member of the Hispanic IT Executive Council, a member of Prospanica (formally the National Society of Hispanic MBAs), a lifetime member of National BDPA, a member of the Information Systems Audit and Control Association, a member of the International Society of Six Sigma Professionals, and former executive member of CompTIA End User Commission.

Mr. Fleming believes in community service and is a lifetime member of the greatest fraternity in the world, Alpha Phi Alpha Fraternity, Inc., a leader of the 100 Black Men of Chicago, Inc., Brother-2-Brother executive speaker at the Thurgood Marshall College Fund Leadership Institute, a volunteer chef of Real Men Cook, and former instructor of Junior Achievement of Chicago.

He is a certified Project Management Professional (PMP), a certified Lean Six Sigma Green (LSSGB) belt professional, and a certified IT Infrastructure Library (ITIL) professional.

He received an Executive Program Certificate from Harvard Business School, Harvard University, Public Education Leadership Project Institute in July 2024, and completed the Executive Leadership Program at Kellogg School of Management, Northwestern University, Center for Nonprofit Management Executive in December 2023.

He received his Bachelor of Science degree in Management from Southern Illinois University at Carbondale and graduated with Distinction by earning a Master of Business Administration (MBA) in Information Systems from DeVry University, Keller Graduate School of Management.

He is from Belize, Central America, and has lived in New York City, Philadelphia, and Baltimore, and currently resides in Chicago. He enjoys major league sports, traveling to the Caribbean, a passionate grill master, and spending quality time with family and friends.

Make America Hope Again is his debut book.