CTO Confessions Brought to you by IT Labs

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209

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May 2026

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About the show

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.

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May 21, 202653 min

Episode 206: Dissecting the CTO Role Misconceptions, Hiring, and the Age of AI with Jay Dalke

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 25 years of experience leading technology across startups, enterprises, and private equity transformations, with a people-first approach that has built high-performing global teams delivering real business outcomes. In this episode: → Why CTOs guide — they don't need to have every answer → Why social EQ isn't a hiring requirement for engineers → The three traits that matter most when building a team: humility, hunger, and intellect → Hard work and natural talent — why it's not a binary choice → AI: separating the fear from the hype "Strength overdone is a weakness, and a weakness overcome is a strength."You said: what is the easiest way to extract audio from video on capcut?

May 12, 202651 min

Episode 205: Behind the Platform Powering Modern Background Checks with Luca Bonmassar

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-founded and sold three startups. He's one of the rare CTOs who moves as comfortably in a business conversation as a technical one. In this episode: → Why understanding the business side isn't optional for a CTO → The surprising complexity of data that still exists only in physical form → Why hiring fast and firing faster may cost you more than you think → His philosophy on over-engineering — and why patience often wins "It's better to be late knowing that what you build will have greater impact than building things and hoping someone will use them one day."

May 7, 202649 min

Episode 204: How fast is technology evolving with Ahmed Abdelrahman

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 from the ground up. He shares why the pace of innovation should feel like opportunity — not pressure — and how the most underrated leadership skill isn't technical at all. In this episode: → Why you should ask what demotivates people, not just what motivates them → How psychological safety turns failure into fuel → The case for hackathons as a team-building tool → Why articulating ideas clearly is a career accelerator most engineers ignore "If you create psychological safety for your team, they will see failure as an opportunity, not as a shameful mistake."

April 1, 202644 min

Episode 203: Getting Priorities & Requirements Right with Rigvinath Chevala

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 bridge the gap between engineering reality and product goals. In this episode, we explore: The CPTO Trend: Why the dual role is rising and how it aligns managers and engineers. - B2B vs. B2C: Navigating the feedback loop when you don’t have millions of users. - Project vs. Product: Moving away from "one-and-done" thinking toward a recurring growth mindset. - The Art of the "No": Proven methods for prioritizing features based on impact and frequency. "There's not only one way to do certain things. You have to force yourself to say: are there alternatives? That’s where the negotiation begins." Whether you’re a seasoned executive or a fresh tech lead, this episode serves as a practical guide to mastering the "push-pull" of organizational demands.

March 10, 202648 min

Episode 202: Your system doesn’t need heroes - A guide on building and scaling a team

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 after the episode ends. They cover why hiring fast isn't the same as hiring right, why 2 a.m. firefighting is a red flag (not a badge of honor), and why AI without purpose is just noise. Whether you're managing your first team or leading an entire engineering org, this one's for you. What you'll take away: → 2 a.m. problem-solving isn't hustle culture — it's a broken system → AI needs a clear purpose, or it has no place → Don't scale the system before the business is ready → Ditch the formal meetings. Build a culture of ongoing communication instead About Swarnim Kumari: Swarnim is an engineering leader with experience across Senior Engineer, Engineering Manager, and Director of Engineering roles. She specializes in scaling high-performing teams, improving delivery practices, and building reliable, customer-focused systems — always at the intersection of technology, product, and people.

March 4, 202648 min

Episode 201: What it takes to build great innovative hardware with Nico Cormier

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. Nico draws on his experience at Cisco, Nasdaq, and DxO Labs to share what separates hardware teams that succeed from those that don't. In this episode: - Why CTOs need to be business builders, not just tech experts - The brutal reality of hardware risk — and why it's still worth it - How to listen to user feedback without cherry-picking the good stuff - Staying mission-driven while staying open to change "Nothing beats being able to hold a product in your hands." — Nico Cormier

January 9, 202646 min

Episode 200: Reimagining Healthcare in the US with Ravin Soni

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.

December 24, 202532 min

Episode 199: How to Build Tech Without Chasing Perfection

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.

December 16, 202535 min

Episode 198: People, Architecture, and the Cross-Team Perspective

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.

December 10, 202540 min

Episode 197: Beyond Bitcoin: How Blockchain is shaping the Future

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.