DiscoverCEO Tech LiveFrom Help Desk to CIO (The Leader Who Made it Possible) - Wintrust Financial Corporation, Mike Ryan
From Help Desk to CIO (The Leader Who Made it Possible) - Wintrust Financial Corporation, Mike Ryan

From Help Desk to CIO (The Leader Who Made it Possible) - Wintrust Financial Corporation, Mike Ryan

Update: 2025-09-11
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From help desk to CIO. That’s the remarkable journey of Mike Ryan, Executive Vice President and Chief Information Officer at Wintrust Financial Corporation.

In this episode, Mike reveals how he transformed his career from marketing to IT leadership, ultimately rising to the C-suite after nearly three decades at Wintrust.

Along the way, he embraced risks, learned through failure, and carried forward the leadership wisdom and advice of a true mentorswho believed in him.

You’ll discover:

-The pivotal moment that launched Mike’s mission to lead from the top.

-How a single career mistake reshaped his leadership approach.

-Why creating a culture that supports failure leads to stronger teams.

-What it really takes to move from the ground floor to the executive level.

If you’ve ever wondered what’s possible when you bet on yourself — and your people — this conversation will inspire you to see your own path from where you are now to where you want to be.

Follow Mike on LinkedIn - https://www.linkedin.com/in/mike-ryan-6bb3262/

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The episode is powered by Hexaware: The IT services company creating smiles through great people and technology.

Go here to learn more: https://hexaware.com/

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From Help Desk to CIO (The Leader Who Made it Possible) - Wintrust Financial Corporation, Mike Ryan

From Help Desk to CIO (The Leader Who Made it Possible) - Wintrust Financial Corporation, Mike Ryan