How can we separate real innovation from hype? 

In this episode, Joel Krooswyk, Federal CTO at GitLab, joins TC Gill for a thoughtful deep dive into the evolving role of AI in development, hiring, and leadership. Joel brings 25+ years of experience across private and public sectors and this conversation hits that perfect balance of vision and pragmatism. 

Tune in now and explore the full story!


Episode 183: An AI Give-and-Take with Joel Krooswyk

Can good leadership be taught or does it come down to who you are?

In this episode, we sit down with Wes Bailey, Founder at Par Not Far, for a refreshingly honest conversation about leadership, bureaucracy, and why some of today’s sacred practices might need to go.

If you’re tired of corporate speak and want something real, this is the episode for you.

Episode 184: Do Good Leaders Get to the Top? A Discussion with Wes Bailey

In this episode of CTO Confessions, we sit down with Reinaldo Ynchaustegui, CTO in the asset management space, for an overview of what it really takes to lead in tech. From dissecting how to automate a tech team’s workflow without losing the human touch to exploring the critical role of emotional intelligence in leadership, Reinaldo shares insights from the frontlines. 

Tune in to hear the realities behind the role and the balance between tech and people.

Episode 185: Leading at the Intersection of Technology and Finance with Reinaldo Ynchaustegui

What can the Marines teach us about leading high-performing tech teams? A lot more than you might think.

In this episode, Bob Hackney, CTO at PerfectServe, shares how a mission-first mindset translates from the battlefield to the boardroom, delivering results without sacrificing your people. His “double win” approach is all about achieving objectives while growing and empowering teams.

Whether you’re scaling a tech org, running global teams, or simply looking to lead with empathy and impact, this conversation will challenge and inspire you.

Episode 186: Lessons from the Marines and Tech with Bob Hackney

Allen Cheung, SVP of Engineering at UJET.cx, sat down with our host TC Gill for our podcast CTO Confessions to explore how AI is reshaping the tech industry and why some programmers resist this transformation.


Whether you’re building teams, navigating the shift to AI-powered engineering, or simply looking to embrace growth through change, this conversation will challenge and inspire you.

Episode 187: Programmers' Resistance in the Age of AI with Allen Cheung

Naresh Singh, Partner and CTO at Lenox Advisors, sat down with our host TC Gill for our podcast CTO Confessions to discuss how technology is reshaping wealth management from AI-driven data systems to leadership grounded in both technical foresight and servant leadership.

Whether you’re navigating financial services, driving transformation through technology, or leading high-performing teams, this conversation will inspire and equip you with practical insights.

Episode 188: Wealth Management Driven by Technology with Naresh Singh

Aleksandra Gjinovska, Head of Technology at IT Labs, sat down with our host TC Gill for our podcast CTO Confessions to share her journey as a woman leading in a male-dominated industry and how mentorship, saying no, and organizational support shape future leaders.

Whether you’re scaling teams, mentoring future leaders, or striving to foster inclusive leadership, this conversation is full of insights that will inspire and challenge you.

Episode 189: Connecting the Dots in Tech Leadership with Aleksandra Gjinovska

Technology is advancing faster than ever, but what keeps it meaningful is the human side behind the solutions.

In this episode, Falko Buttler, CTO at Lantern, shares how he balances innovation with empathy, scaling tech platforms that support people through life’s most sensitive moments. From early iOS development to leading large-scale transformation, Falko brings insights on building tech that truly serves.

This conversation is a reminder that even in an age of AI, leadership must be anchored in human connection.

Episode 190: In a World of AI, Let’s not Forget the Human with Falko Buttler

How do you lead through culture shifts, acquisitions, and organizational change, without losing sight of people?

In this episode, Adan Pope, Senior VP at TAG, shares insights on leadership during high-stakes transitions. From building tension maps to understanding organizational dynamics, his perspective highlights how leaders can turn uncertainty into clarity and growth.

This conversation is a masterclass in leading with methodology, empathy, and foresight during times of change.

Episode 191: There Are No Mergers, Only Acquisitions with Adan Pope

In this thought-provoking episode, Wes Bailey returns for round two with TC Gill to explore one of the boldest questions in tech leadership today: what happens when innovation, AI, and adaptability redefine the very essence of a CTO?

This conversation is part wake-up call, part survival guide for the future of tech leadership and it might just make you rethink your next career move.

Episode 192: We Don’t Need CTO’s Anymore with Wes Bailey

Hosted by TC Gill, this podcast explores the dynamic world of technology leadership. Each episode explores the challenges, strategies, and stories that shape the lives of today’s CTOs and tech leaders.  

From navigating complex business issues to leading high-performing teams, CTO Confessions sheds light on the multifaceted role of technology executives, highlighting the critical decisions they make and the impact they have on organizations.  

Join us as we unpack the realities of tech leadership and share insights that rarely get the appreciation they deserve, all with a healthy dose of curiosity and candor. 

Brought to you by IT Labs.

Episode 191: There Are No Mergers, Only Acquisitions with Adan Pope

CTO Confessions

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