As business clients expect more proactive, informed banking, innovative community and regional banks are using AI to help commercial bankers spot opportunities earlier, engage prospects with more relevance, and bring consistency to business development. The premise is simple: AI won’t replace relationship managers – it helps them know who to call, why, and what to discuss. This session follows one community bank from pilot to bank-wide rollout across its relationship-manager teams, what the market managers actually experienced, the operating-model changes it required, and the results it produced. Such transformation is enabling banks of any size to compete for commercial relationships against the AI budgets of the largest banks.

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.

Welles Borie is a Principal Technical Product Manager at FIS, where he leads strategy and development for the FIS Origination Suite—a unified digital platform that helps financial institutions automate account opening, lending, and credit card applications for both consumers and small businesses.

Welles has more than 15 years of experience building financial software and scaling fintech platforms. Before joining FIS through its 2025 acquisition of Amount, he was the Principal Product Manager for Amount’s small business segment, where he delivered flexible lending and account opening. His career also includes serving as Senior Director of Product at Linear Financial Technologies and holding several key product roles at Fundation, where he helped expand its digital lending-as-a-service platforms. He started his career at J.P. Morgan, spending five years working across mortgage advisory, financial sponsors, and alternative investment groups. Welles holds a bachelor’s degree from Hamilton College.

Carlos Lopez serves as the Senior Analyst supporting Digital Banking, Core Banking, and Treasury Management for Corporate Strategy at Jack Henry & Associates. His thought leadership centers around analyzing market trends, identifying vendors of interest, & evaluating competitive intelligence to help drive company roadmaps and close solution gaps. 

Small business owners do not wake up thinking about banking. They wake up thinking about making payroll, managing cash flow, finding customers, retaining employees and growing their businesses. Yet as economic uncertainty, technological change and competitive pressures continue to accelerate, the role banks play in helping business owners navigate these challenges has never been more important.

In this keynote session, Heather Kesner will challenge attendees to view the future of banking through a different perspective: the perspective of the owner. Drawing on insights from serving millions of small businesses, Kesner will explore how banks can build stronger relationships and deliver more meaningful value by understanding the day-to-day realities entrepreneurs face.