In the Season Finale of The Iteration Lab, Mike Corbett sits down with Dave Gillespie, Executive Vice President of Infrastructure & Modernization at CIBC, to explore the technology foundations that power modern banking.

Dave shares lessons from a career spent operating and modernizing complex enterprise systems that support millions of transactions every day. From building resilient infrastructure to leading large engineering organizations, he reflects on what it takes to evolve critical platforms while maintaining the reliability that financial institutions demand.

The conversation explores the realities of modernizing legacy systems, scaling technology across large organizations, and empowering teams to solve complex problems together. Dave also reflects on the mentors and experiences that shaped his leadership approach—from early technical roles to building high-performing teams responsible for some of the most important systems inside the bank.

Beyond technology, Dave shares personal perspectives on leadership, community involvement, and how experiences outside of work - from volunteering to backcountry skiing - have shaped how he thinks about preparation, risk, and responsibility.

This episode offers a thoughtful look at the people and systems behind modern banking - and the leadership required to support their evolution.

About the Show

The Iteration Lab explores how leaders are shaped by their history, their heroes, their heartbreaks, and their hopes.

Hosted by Mike Corbett, each episode features candid conversations with business and technology leaders navigating complexity, change, and high-stakes decisions.

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