CTO Confessions Brought to you by IT Labs

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 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?

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."

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."

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.