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
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.
Jun 24, 2025 • 43min
Episode 179: From Cinematography to Strategic Marketing with Chris Geiser
From cinematography to the C-suite? Yes, you read that right. In this episode, TC Gill talks with Chris Geiser, CTO at DCG ONE, about an unconventional leadership journey that blends creativity, marketing, and tech strategy.
If you’re into leadership lessons with a personal twist, this one’s for you.
Jun 17, 2025 • 51min
Episode 178: Creating Harmony in a Scaling Company Fueled by Acquisitions with Ed Federici
What happens when a company grows through acquisitions but wants to keep the startup spirit alive?
In this episode, TC Gill sits down with Ed Frederici, CTO at Appfire, to explore how to build harmony in a scaling tech company, without crushing innovation. From preserving entrepreneurial culture to building strong, autonomous teams, this one’s packed with insight.
Jun 10, 2025 • 56min
Episode 177: Building End to End Solutions for Health & Wellness Marketing with Oleg Korenfield
This week, TC Gill is joined by Oleg Korenfeld, CTO at CMI Media Group, to unpack how technology transforms health and wellness marketing. From traditional media to data-driven strategies, Oleg shares insights on building scalable solutions that deliver real campaign value.
Expect stories on innovation, strategic tech adoption, and the evolving role of marketing tech leaders.
Jun 3, 2025 • 45min
Episode 176: Why Purpose Beats Features: Designing for Outcomes with Drew Morrell
What makes great tech solutions truly effective? It’s not features, it’s outcomes. In this episode, TC Gill speaks with Drew Morrell, Head of Engineering at Workiva, about why user-centered design, agile thinking, and purposeful product development matter more than feature counts.
Tune in for insights that cut through the noise and get to the core of what product teams should focus on.
