CTO Confessions Brought to you by IT Labs

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 systems, and leading teams through real change. From staying close to the technical craft as a leader, to rethinking motivation, to why healthcare still needs urgent digitization, this conversation is a thoughtful reminder that the best leaders ask more than they assume — and listen more than they speak.

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 change, from navigating self-doubt to introducing AI in ways that support people instead of overwhelming them. This is a warm, honest conversation about progress, simplicity, and why your people matter far more than any tech stack ever will.

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 as engineers move into leadership roles ✅ The hidden challenges of cross-team architecture and modern GenAI frustrations ✅ Why leadership can become lonelier the higher you go 💡 “The higher you go up in an organization, the lonelier it can be.” – Alexandre Goedert Whether you’re leading multiple teams, navigating complex architectures, or growing into senior leadership, this conversation offers thoughtful perspectives on building healthy teams and scalable systems—without losing the human side of tech.

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 — and why patience might be its greatest advantage.

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.

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 masterclass in leading with methodology, empathy, and foresight during times of change.