Building, creating, developing – these are all activities all tech leaders simply love. And as leaders, they are skilled at nurturing the flames of others – the flames to build, create, develop, analyze, or simply put, to follow their drive towards creating a better tomorrow. I had the chance to have a good talk with one such leader – Jamie Smith Webb, CTO at Numan, who shared with me his journey to becoming a tech leader, his experience in various industries, and his incredible insights he’s amassed from working with a variety of teams.

Key takeaways from the podcast are: 

- Composing your team is a matter of adaptibility and proper leadership, especially when they are diverse in nature 

- Knowing how and when to ask for help will help you grow, but also establish relationships 

- Setting expectations - understanding and aligning expectations is crucial for effective leadership on all levels 

Our Guest: Jamie Smith Webb 
LinkedIn: https://www.linkedin.com/in/jamiesmithwebb/ 
Website: https://www.numan.com/ 

Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

Episode 137: From TechEnthusiast to TechLeader: A Building and Leading Journey with Jamie Smith Webb

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 conversation will inspire and equip you with practical insights.

Episode 188: Wealth Management Driven by Technology with Naresh Singh

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 insights that will inspire and challenge you.

Episode 189: Connecting the Dots in Tech Leadership with Aleksandra Gjinovska

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 truly serves.

This conversation is a reminder that even in an age of AI, leadership must be anchored in human connection.

Episode 190: In a World of AI, Let’s not Forget the Human with Falko Buttler

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.

Episode 191: There Are No Mergers, Only Acquisitions with Adan Pope

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.

Episode 192: We Don’t Need CTO’s Anymore with Wes Bailey

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.

Episode 193: A Conversation about Terminators and Lasers with Michael Natkin

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.

Episode 194: How to Deploy with Confidence in 2025 with Eddie Pecker

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.

Episode 195: The Case for Democratizing Tech with Andrew Overholt

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.

Episode 196: How to Catalyze Chaos in Tech with Kader Sakkaria

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.

Episode 137: From TechEnthusiast to TechLeader: A Building and Leading Journey with Jamie Smith Webb

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