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
Nov 20, 2025 • 39min
Episode 196: How to Catalyze Chaos in Tech with Kader Sakkaria
Chaos isn’t the enemy, unmanaged chaos is.
In this episode, Kader Sakkaria, Global Head of Data Technology (DoE) and Delivery at Gallagher, joins TC Gill to unpack why chaos can actually fuel innovation when leaders know how to harness it.
From cultural transformation to navigating complexity in fast-moving environments, this conversation is a practical guide for tech leaders looking to turn disruption into opportunity.
Nov 11, 2025 • 1h 17min
Episode 195: The Case for Democratizing Tech with Andrew Overholt
In this episode, Andrew Overholt, VP of Engineering at Mozilla, joins TC Gill to explore how Mozilla lives its mission, putting users first, leading with humility, and shaping the future of an open and accessible internet. From policy to innovation, Andrew shares how democratizing tech can (and should) influence how we build the web.
Nov 4, 2025 • 58min
Episode 194: How to Deploy with Confidence in 2025 with Eddie Pecker
In this episode of CTO Confessions, TC Gill sits down with Eddie Pecker, CTO at APEXX, a payment orchestration platform trusted by enterprise companies worldwide. From comparing technical debt to mortgages to breaking down what “deploying with confidence” should look like in 2025, Eddie brings a refreshingly practical view of leadership, AI, and security in fast-moving tech teams.
Oct 16, 2025 • 52min
Episode 193: A Conversation about Terminators and Lasers with Michael Natkin
From Hollywood special effects to cutting-edge AI - this episode covers it all.
Join Michael Natkin, Former SVP of Software Engineering at Glowforge, and TC Gill as they dive into why AI is imperative in today’s tech landscape, how creativity and innovation intersect, and what leaders can do to keep their teams inspired in the age of automation.
Oct 9, 2025 • 57min
Episode 192: We Don’t Need CTO’s Anymore with Wes Bailey
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.
Sep 25, 2025 • 40min
Episode 191: There Are No Mergers, Only Acquisitions with Adan Pope
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.
Sep 18, 2025 • 46min
Episode 190: In a World of AI, Let’s not Forget the Human with Falko Buttler
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.
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.
