Head of Business and Community Banking Strategies
Wintrust
Oscar D. Johnson, Jr. joined Wintrust in 2025 and serves as the Executive Vice President of Business and Community Banking which includes oversight of Wintrust’s SBA offering.
Prior to Wintrust, Oscar spent 11 years at BMO where he led Business Banking in the U.S. before transitioning to lead Treasury Management Sales in his last role. He served in varying leadership roles prior to BMO at LaSalle Bank, CIBC and Associated Bank.
His roles in Financial Services and within the Chicago community have shaped his reputation as an experienced banker, passionate leader, strategic planner and analytical thinker.
He currently serves on the boards of UCAN and the Oak Park River Forest Community Foundation. He recently rolled off the boards at the Lincoln Park Zoo, Allies for Community Business and IFF. He’s intentional about providing access to opportunity for those in need and his life’s mission is to serve others in board seats and through mentorship.
Oscar is originally from Milwaukee, WI. He’s a graduate of Howard University and earned an MBA from Marquette University.
Women-owned businesses represent 42% of all U.S. businesses yet receive just 4% of small business loan dollars. This session explores the largely untapped market opportunity represented by underserved entrepreneurs—and the specific tools, data sources, and underwriting models allowing institutions to say yes to more small businesses profitably and at scale. Industry leaders will examine how AI-powered underwriting is making it possible to evaluate non-traditional data, reduce decision-making subjectivity, and extend credit to businesses traditional models have historically passed over. The discussion will address what it actually takes to build or expand a lending program that reaches minority-, women-, and rural-owned businesses without expanding risk—and how the institutions doing it right are turning inclusive lending into a genuine competitive advantage.