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Artwork for CTO Confessions Brought to you by IT Labs

CTO Confessions Brought to you by IT Labs

IT Labs
Leadership
Healthcare
Change Management
Artificial Intelligence
Generative AI
Cybersecurity
Agile Methodology
Digital Transformation
Software Development
Collectors
Trust In Leadership
Feedback Loop
Continuous Learning
Innovation
Technology Leadership
Data Management
Trading Cards
Operational Efficiency
Data Silos
User Experience

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... more

PublishesTwice monthlyEpisodes210Founded6 years ago
Number of ListenersCategory
Technology

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Artwork for CTO Confessions Brought to you by IT Labs

Latest Episodes

Episode 207: Feedback loops, optimizing campaigns, and leading with Dustin Jackson 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 f... more

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 meaningf... more

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-performin... more

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 bri... more

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... more

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 d... more

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 comple... more

Key Facts

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Recent Guests

Dustin Jackson
CTO of Video Amp
Video Amp
Episode: Episode 207: Feedback loops, optimizing campaigns, and leading with Dustin Jackson
Jay Dalke
CTO of AbaxHealth, focused on improving revenue and outcomes for health systems
AbaxHealth
Episode: Episode 206: Dissecting the CTO Role Misconceptions, Hiring, and the Age of AI with Jay Dalke
Luca Bonmassar
Chief Technical Officer at Checkr
Checkr
Episode: Episode 205: Behind the Platform Powering Modern Background Checks with Luca Bonmassar
Ahmed Abdelrahman
CTO at Bayzat (UAE/Saudi Arabia)
Bayzat
Episode: Episode 204: How fast is technology evolving with Ahmed Abdelrahman
Rigvinath Chevala
Chief Product and Technology Officer at ServiceChannel
ServiceChannel
Episode: Episode 203: Getting Priorities & Requirements Right with Rigvinath Chevala
Nico Cormier
CTO at Remarkable (the paper tablets company)
Remarkable
Episode: Episode 201: What it takes to build great innovative hardware with Nico Cormier
Ravin Soni
VP of Engineering at Curative
Curative
Episode: Episode 200: Reimagining Healthcare in the US with Ravin Soni
Alexandre Goedert
VP of Engineering at SurePay
SurePay
Episode: Episode 198: People, Architecture, and the Cross-Team Perspective
Tim Sabanov
CTO at Zumo, a fintech focused on secure access to digital assets.
Zumo
Episode: Episode 197: Beyond Bitcoin: How Blockchain is shaping the Future

Host

Dr. Thomas Gill
Host of the show, technology leadership-focused interviewer and moderator.

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Hard Fork
Hard ForkThe New York Times
Better Offline
Better OfflineCool Zone Media and iHeartPodcasts

Talking Points

Recent interactions between the hosts and their guests.

Episode 207: Feedback loops, optimizing campaigns, and leading with Dustin Jackson
Q: Tell us what Video Amp does and who it serves.
Video Amp operates in ad tech to help agencies, brands, and large media companies understand who is watching what online, providing measurement that is apples-to-apples across buyers and sellers, with a core deterministic methodology and AI-assisted enhancements.
Episode 205: Behind the Platform Powering Modern Background Checks with Luca Bonmassar
Q: What is your approach to architecture decisions and when to rewrite or iterate?
Avoid big rewrites when possible; prefer incremental improvements with compatible services, and use one-way vs two-way door thinking to decide how much freedom teams have to experiment.
Episode 205: Behind the Platform Powering Modern Background Checks with Luca Bonmassar
Q: How do you handle technical debt and communicate its cost to the business?
You frame debt in terms of opportunity cost and impact on velocity, using concrete examples from incidents and outages to quantify the cost and then discuss trade-offs with the business.
Episode 205: Behind the Platform Powering Modern Background Checks with Luca Bonmassar
Q: What is the role of the CTO in your view, beyond engineering leadership?
The CTO is the voice of technology in the executive team, shaping technology strategy and the product roadmap, while educating the business about why tech decisions matter and ensuring alignment across functions.
Episode 200: Reimagining Healthcare in the US with Ravin Soni
Q: What tips do you have around creating the best team?
Hire people that you think are going to be good teammates, as collaboration is key to team success.

Audience Metrics

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Frequently Asked Questions About This Podcast

What is This Podcast about and what kind of topics does it cover?

This series centers on technology leadership and the realities of running modern engineering organizations. Episodes typically feature CTOs, CPTOs, and senior engineering leaders discussing how they balance technical vision with business goals, manage teams and culture, and navigate fast-moving tech trends such as AI, DevOps, data governance, and product strategy. Notable throughlines include the shift toward cross-functional leadership, the importance of psychological safety and stakeholder education, and pragmatic approaches to scaling platforms and aligning technology with business outcomes. The lineup frequently highlights lessons on hiring, governance, architecture, and the human side of leading technical teams, offering actionable ins... more

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this podcast launched 6 years ago and published 210 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on this podcast?

Recent guests on this podcast include:

1. Dustin Jackson
2. Jay Dalke
3. Luca Bonmassar
4. Ahmed Abdelrahman
5. Rigvinath Chevala
6. Nico Cormier
7. Ravin Soni
8. Alexandre Goedert

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