Mike Ryan, EVP and CIO of Wintrust Financial Corporation, has helped transform the bank’s technology strategy and software stack. Now, he’s tackling one of the biggest questions facing every technology leader: How do you separate real AI value from the hype?

In this episode of CEO Tech Live, Mike joins host Ben Fanning to explore what organizations are getting right—and wrong—about AI, why governance and security have to come before speed, and what it takes to bring technology and the business together to drive real transformation.

Mike also shares the leadership shift he had to make after becoming CIO, why getting out of the weeds created greater strategic impact, and how he’s already using AI to save hours of time.

Follow Mike Ryan on LinkedIn

Learn more about Wintrust

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/

Raj Chandrasekhar has spent his career leading technology at the highest levels. As Chief Technology and Innovation Officer at Consilio, he helps oversee AI and technology supporting more than 30,000 legal matters and 2 billion documents every year, where mistakes can carry enormous legal and financial consequences.

But the leadership lesson that shaped him most had nothing to do with technology.

It began with a phone call from an employee at the airport, a decision to put family ahead of work, and a moment that forever changed how Raj thinks about leadership.

That one difficult leadership moment forced Raj to rethink how he leads, and he still carries that lesson with him today.

In this episode of CEO Tech Live, Raj shares:

• Why empathy is one of the most underrated competitive advantages in leadership
• The leadership mistake he still regrets—and how he repaired the trust afterward
• Why knowledge without humility fails, and humility without knowledge isn't enough
• Why AI is advancing faster than governance can keep up
• How leaders should think about protecting sensitive data in the AI era
• Why partnerships consistently outperform vendor relationships
• How Raj is building his own private AI "Jarvis" at home to stay ahead of emerging technology

As AI transforms every industry, Raj believes the leaders who win won't simply adopt the newest technology.

They'll be the ones who combine innovation with empathy, humility, trust, and sound judgment.

Follow Raj Chandrasekhar on LinkedIn

Learn more about Consilio

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/

How do you inspire more than 1.1 million people to come together—not because they're paid to, but because they believe in a shared purpose?

Rajneesh Gupta, Global Head of Products & Partnerships / Partner and Managing Director at AlixPartners, experienced exactly that while helping organize the World Culture Festival in Washington, D.C., where volunteers from around the world united to create one of the largest cultural gatherings ever held.

The experience fundamentally changed how he thinks about leadership, motivation, and building teams capable of accomplishing what seems impossible.

In this episode of CEO Tech Live, Rajneesh shares:

• The leadership lesson behind organizing an event attended by 1.1 million people
• Why inspiration consistently outperforms authority and management
• How one painful leadership challenge taught him that how you lead matters just as much as what you accomplish
• Why meditation has become his most valuable professional development tool
• How authenticity creates trust—and trust creates high-performing teams
• The framework he uses to build successful partnerships across global organizations
• Why great leaders help people see they're "building a cathedral," not just "breaking stones"

As organizations race to adopt AI and navigate constant change, Rajneesh believes the leaders who create the biggest impact won't simply manage people.

They'll inspire them with a purpose bigger than themselves.

Follow Rajneesh Gupta on LinkedIn

Learn more about AlixPartners

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/