CTO Confessions Brought to you by IT Labs

Most people think the CTO has all the answers. Jay Dalke would disagree. In this episode of CTO Confessions, TC Gill sits down with Jay Dalke, CTO at AbaxHealth, to explore what the role actually looks like from the inside — the misconceptions that follow it, the hiring instincts that hold up over time, and how to think clearly about AI when the noise around it is louder than ever. Jay brings over...

Background checks sound straightforward. Until you try to build the infrastructure behind them at scale. In this episode of CTO Confessions, TC Gill sits down with Luca Bonmassar, CTO of Checkr — a platform that helps millions of people find meaningful work and helps companies hire with confidence. Luca brings over 20 years of experience across Fintech, Crypto, Social Media, and AI/ML, and has co-...

Technology isn't slowing down. And neither are the expectations placed on the people leading it. In this episode of CTO Confessions, TC Gill sits down with Ahmed Abdelrahman, CTO at Bayzat, to talk about what it actually takes to build high-performing engineering teams when the ground keeps shifting underneath you. Ahmed brings nearly two decades of experience scaling secure, distributed platforms...

Is the push-pull of feature prioritization giving you a headache? You aren't alone. In this episode, TC Gill sits down with Rigvinath Chevala, CPTO at ServiceChannel, to strip away the hype and get into the real grit of tech leadership. Rigvinath brings over 20 years of experience scaling B2B SaaS from $10M to $180M. He breaks down why the "sexy" AI solution isn't always the right one and how to b...

Your system doesn't need heroes — A guide on building and scaling a team "If your system needs heroes, you don't have a system." In this episode of CTO Confessions, TC sits down with engineering leader Swarnim Kumari for a candid conversation on what it actually takes to build and scale high-performing teams. No fluff — just hard-earned lessons and sharp one-liners that'll stick with you long afte...

What does it really take to build great hardware in a software-first world? In this episode of CTO Confessions, we sit down with Nico Cormier, CTO of reMarkable — the company behind the world's leading paper tablet — to explore what modern hardware development actually looks like from the inside. We get into the risks, the rewards, and the mindset it takes to ship a physical product people love. N...

Assuming you know what motivates people is often what disconnects you from them. In this episode of CTO Confessions, Ravi Soni, VP of Engineering at Curative, shares why strong leadership starts with curiosity — not conclusions — especially in complex, high-stakes environments like healthcare. Ravi brings a calm, practical perspective shaped by years of scaling SaaS platforms, modernizing legacy s...

Trying to build things perfectly is often what stops them from working at all. In this episode of CTO Confessions, Stephen Cope, CIO at Astrak, shares why aiming for 80% is usually more than enough — and how letting go of perfection helps teams move faster, learn sooner, and build technology that actually gets used. Stephen brings a thoughtful, grounded perspective shaped by years of leading real...

Alexandre Goedert, VP of Engineering at SurePay, sat down with our host TC Gill for our podcast CTO Confessions to discuss what it really means to lead from the core—where people, architecture, and cross-team alignment intersect. 💬 What you’ll hear in this episode: ✅ Why architecture should start within teams—but needs cross-team alignment at scale ✅ How people and soft skills become critical a...

Regulation isn’t a roadblock; it’s the guardrail helping blockchain grow up. In this episode, Tim Sabanov, CTO at Zumo, joins TC Gill to break down the hype, the misconceptions, and the slow-but-purposeful pace of regulation shaping the future of digital assets. From decentralization to the Web2–Web3 shift, this conversation gives tech leaders a clear, grounded view of where blockchain is headed —...

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 disru...

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.

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.

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.

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.

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 ma...

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 t...

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 insigh...

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...

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.

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...

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 realitie...

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.

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!

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 ed...