CEO Tech Live

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/

Amjad Masad faced one of the hardest decisions of his career.

Replit had grown too fast, AI adoption hadn't arrived as quickly as expected, and the company was running out of runway. After painful layoffs and a dramatic restructuring, many would have played it safe.

Instead, Amjad doubled down.

He and the team locked themselves in a "war room", bet the company on AI agents, and launched what became one of the first software creation agents on the market.

The result?

Replit's revenue exploded, the company scaled from roughly a $1 billion valuation to $9 billion, and millions of people gained a new way to build software.

In this episode of CEO Tech Live, Amjad shares:

• Why great startups often begin with a "delusion"

• The painful leadership decisions that saved Replit

• Why every job is becoming more entrepreneurial

• How AI is moving from prompting to autonomous execution

• Why distribution, audience, and trust may matter more than coding skills

• The leadership principle Replit calls "Seek Pain"

• What the future of software development looks like when anyone can build

If execution is no longer the bottleneck, what becomes the competitive advantage?

According to Amjad, it's ideas, leadership, and the ability to get those ideas into the hands of people.

---

Follow Amjad on LinkedIn

Learn more about Replit

---

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/

What if the next major breakthrough in healthcare isn't a new drug, a new technology, or even AI?

What if it's the data we already have?

Darren Coleman, CIO of Envision Pharma Group, shares how healthcare's biggest challenge isn't a technology problem—it's a data problem.

Healthcare generates more data than any industry on earth, yet only a fraction of it is being used to improve patient outcomes, accelerate research, and unlock the promise of personalized medicine.

In this episode of CEO Tech Live, Darren shares:

• Why healthcare may be sitting on its greatest breakthrough already

• What Operation Warp Speed revealed about the future of medicine

• How better access to data could accelerate treatments and clinical discoveries

• Why AI is creating new opportunities rather than simply replacing jobs

• The leadership lesson that transformed him from a struggling first-time manager into a successful executive

• How to lead change by "breadcrumbing" ideas instead of forcing them on people

• Why the best technology leaders understand both business and technology

Darren's journey is an unconventional one. He started in sales and marketing, was unexpectedly pulled into technology nearly 30 years ago, and discovered that the most effective leaders aren't the smartest people in the room—they're the people who help others become the best version of themselves.

If the future of healthcare depends on connecting data, technology, and people, this conversation offers a compelling look at what comes next.

----

Follow Darren on LinkedIn

Learn more about Envision Pharma Group

----

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/

AI isn’t magic.

Kevin Bates, Chief Data Officer at T. Rowe Price, made the clearest case I’ve heard for why so many companies are stuck with AI.

Everyone wants the AI breakthrough.

But Kevin says the real blocker is often much less exciting:

fragmented data

legacy systems

unclear ownership

poor data quality

decades of complexity

When ChatGPT first exploded, a lot of leaders thought AI might magically work around messy data.

Kevin says the opposite happened.

AI made data quality more important, not less.

Because if your data is broken, fragmented, or trapped in brittle legacy systems, AI won’t transform the business.

It will expose the weakness.

And Kevin’s warning is important to consider:

If your data keeps you from adopting the next generation of tools, you’re not going to compete.

Your AI strategy is only as strong as your data, and Kevin gives us a powerful playbook for where to start!

Follow Kevin on LinkedIn: https://www.linkedin.com/in/kevin-bates-69b3002?utm_source=share_via&utm_content=profile&utm_medium=member_ios

---

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/

Tracy Galloway, Corporate Vice President and COO of Microsoft Americas, shares a powerful framework that every leader needs right now...

...how too keep your leadership impactful while technology moves faster than ever.

This isn't AI hype.

It's a real conversation about:

• nonstop learning

• proving AI ROI

• tackling burnout

• staying present with teams while everything changes

Too many leaders keep layering on:

• AI initiatives

• meetings

• reporting

• workflows

without taking anything off people’s plates.

And eventually leaders wake up wondering why their teams are overwhelmed, disconnected, and losing momentum.

The leaders who win in the AI era won’t just adopt new technology… they’ll learn how to lead differently.

Follow Tracy on LinkedIn - https://www.linkedin.com/in/trgalloway/

---

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/

In the middle of massive transformation, one question keeps surfacing in every boardroom:

Are we behind on AI?

Kelly Fisher, Chief Practice Partner at Wipfli, hears it from leaders every day.

Her answer reframes the conversation:

“AI isn’t replacing your expertise — it’s amplifying it.”

She calls it "Amplified Expertise" — the idea that AI, when used intentionally, helps leaders and their teams make smarter decisions, deliver deeper insights, and free up time for what truly matters.

For CIOs and technology leaders, that means:

-Modeling adoption instead of delegating it.

-Building readiness — data, infrastructure, and culture — so your teams can move from experimentation to enterprise-level execution.

-Guiding with empathy as people adapt to new tools and new expectations.

Kelly also reminded us that innovation starts with people, not platforms

“Bring the joy back to the work that got you in the game in the first place.”

A simple but powerful call to every leader navigating AI and digital transformation today.

Follow Kelly on LinkedIn - https://www.linkedin.com/in/kelly-m-fisher-jd-cpa-mst-9258b23/

---

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/

We live in a world overflowing with dashboards, KPIs, and reports.

But here’s the hard truth: the numbers don’t always tell you the full story.

Rich Brown, Business Transformation Director at LV=, shared a lesson every leader needs to hear:

👉 Early in his career, all the stats said a project was on track.

👉 But his gut told him something wasn’t right.

👉 He ignored it — and later wished he had.

That moment changed his leadership forever.

Now, he always digs deeper when that nagging doubt shows up.

Because while data is essential, instinct is the missing signal.

As leaders, especially CIOs, the pressure to be “data-driven” is immense.

But true transformation comes when you:

-Trust your gut AND the spreadsheets

-Ask the uncomfortable questions

-Lean into intuition as a strategic asset

Your people, your culture, and your instincts will often surface the truth before the metrics do.

Because at the end of the day — it’s not just about technology or process. It’s about people.

💡 How often do you trust your gut as a leader, even when the numbers say otherwise?

Follow Rich on LinkedIn - https://www.linkedin.com/in/ribrown/

---

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/

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/

---

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/