CTO Confessions Brought to you by IT Labs
IT Labs
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.
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.
Episodes
Mentioned books
Sep 9, 2025 • 48min
Episode 189: Connecting the Dots in Tech Leadership with Aleksandra Gjinovska
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.
Sep 2, 2025 • 44min
Episode 188: Wealth Management Driven by Technology with Naresh Singh
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.
Aug 26, 2025 • 53min
Episode 187: Programmers' Resistance in the Age of AI with Allen Cheung
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.
Aug 12, 2025 • 50min
Episode 186: Lessons from the Marines and Tech with Bob Hackney
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.
Aug 5, 2025 • 54min
Episode 185: Leading at the Intersection of Technology and Finance with Reinaldo Ynchaustegui
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.
Jul 29, 2025 • 1h 3min
Episode 184: Do Good Leaders Get to the Top? A Discussion with Wes Bailey
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.
Jul 22, 2025 • 48min
Episode 183: An AI Give-and-Take with Joel Krooswyk
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!
Jul 15, 2025 • 1h 12min
Episode 182: A CTO's Career Guide: Blending Tech and Business with James Long
What happens when deep technical knowledge meets real-world domain expertise?
In this episode, TC Gill is joined by James Long, CTO at Palomar, to explore what it takes to lead with clarity in a high-stakes environment. From modeling risk to building strong, cross-functional teams, this conversation is packed with practical insights for tech leaders.
If you're looking to sharpen your leadership edge, this episode delivers.
Jul 8, 2025 • 43min
Episode 181: Rethinking RTLS: Achieving More with Less Data in the AI Era With Michael Finnegan
In this episode, we sit down with Michael Finnegan, Chief Technology Officer at Cognosos, to rethink what’s possible with RTLS (Real-Time Location Services) in the AI era.
Michael shares how he’s achieving more with less data, offering a fresh perspective on crafting smarter, scalable tech solutions. From reimagining product development to embracing real-time insights, this episode is packed with practical takeaways for tech leaders.
Tune in now and discover how to flip the script on traditional tech thinking.
Jul 1, 2025 • 49min
Episode 180: The Secret to Great Customer-Centric Software with Chris Huff
What makes great software truly customer-centric?
In this week’s episode, Chris Huff, former CTO at Rent Group, joins TC Gill to break down the real secret behind building products that actually serve users. Spoiler: it’s not about adding more features.
