최고 Cto Confessions 팟캐스트 (2025)

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Episode 196: How to Catalyze Chaos in Tech with Kader Sakkaria 39:13

5d ago39:13

39:13

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 practi…

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Episode 195: The Case for Democratizing Tech with Andrew Overholt 1:17:19

14d ago1:17:19

1:17:19

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.…

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Episode 194: How to Deploy with Confidence in 2025 with Eddie Pecker 58:16

21d ago58:16

58:16

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 se…

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Episode 193: A Conversation about Terminators and Lasers with Michael Natkin 51:40

1M ago51:40

51:40

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.…

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Episode 192: We Don’t Need CTO’s Anymore with Wes Bailey 57:09

2M ago57:09

57:09

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 …

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Episode 191: There Are No Mergers, Only Acquisitions with Adan Pope 39:41

2M ago39:41

39:41

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 i…

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Episode 190: In a World of AI, Let’s not Forget the Human with Falko Buttler 46:14

2M ago46:14

46:14

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 transformati…

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Episode 189: Connecting the Dots in Tech Leadership with Aleksandra Gjinovska 48:26

3M ago48:26

48:26

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 inclusiv…

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Episode 188: Wealth Management Driven by Technology with Naresh Singh 43:55

3M ago43:55

43:55

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 te…

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Episode 187: Programmers' Resistance in the Age of AI with Allen Cheung 53:14

3M ago53:14

53:14

Allen Cheung, SVP of Engineering at UJET.cx, sat down with our host TC Gill for our podcast CTO Confessions to explore how AI is reshaping the tech industry and why some programmers resist this transformation.Whether you’re building teams, navigating the shift to AI-powered engineering, or simply looking to embrace growth through change, this conve…

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Episode 186: Lessons from the Marines and Tech with Bob Hackney 50:29

4M ago50:29

50:29

What can the Marines teach us about leading high-performing tech teams? A lot more than you might think.In this episode, Bob Hackney, CTO at PerfectServe, shares how a mission-first mindset translates from the battlefield to the boardroom, delivering results without sacrificing your people. His “double win” approach is all about achieving objective…

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Episode 185: Leading at the Intersection of Technology and Finance with Reinaldo Ynchaustegui 53:46

4M ago53:46

53:46

In this episode of CTO Confessions, we sit down with Reinaldo Ynchaustegui, CTO in the asset management space, for an overview of what it really takes to lead in tech. From dissecting how to automate a tech team’s workflow without losing the human touch to exploring the critical role of emotional intelligence in leadership, Reinaldo shares insights…

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Episode 184: Do Good Leaders Get to the Top? A Discussion with Wes Bailey 1:03:12

4M ago1:03:12

1:03:12

Can good leadership be taught or does it come down to who you are?In this episode, we sit down with Wes Bailey, Founder at Par Not Far, for a refreshingly honest conversation about leadership, bureaucracy, and why some of today’s sacred practices might need to go.If you’re tired of corporate speak and want something real, this is the episode for yo…

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Episode 183: An AI Give-and-Take with Joel Krooswyk 47:40

4M ago47:40

47:40

How can we separate real innovation from hype? In this episode, Joel Krooswyk, Federal CTO at GitLab, joins TC Gill for a thoughtful deep dive into the evolving role of AI in development, hiring, and leadership. Joel brings 25+ years of experience across private and public sectors and this conversation hits that perfect balance of vision and pragma…

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Episode 182: A CTO's Career Guide: Blending Tech and Business with James Long 1:12:07

4M ago1:12:07

1:12:07

What happens when deep technical knowledge meets real-world domain expertise?In this episode, TC Gill is joined by James Long, CTO at Palomar, to explore what it takes to lead with clarity in a high-stakes environment. From modeling risk to building strong, cross-functional teams, this conversation is packed with practical insights for tech leaders…

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Episode 181: Rethinking RTLS: Achieving More with Less Data in the AI Era With Michael Finnegan 43:13

5M ago43:13

43:13

In this episode, we sit down with Michael Finnegan, Chief Technology Officer at Cognosos, to rethink what’s possible with RTLS (Real-Time Location Services) in the AI era.Michael shares how he’s achieving more with less data, offering a fresh perspective on crafting smarter, scalable tech solutions. From reimagining product development to embracing…

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Episode 180: The Secret to Great Customer-Centric Software with Chris Huff 48:31

5M ago48:31

48:31

What makes great software truly customer-centric? In this week’s episode, Chris Huff, former CTO at Rent Group, joins TC Gill to break down the real secret behind building products that actually serve users. Spoiler: it’s not about adding more features.저자 IT Labs

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Episode 179: From Cinematography to Strategic Marketing with Chris Geiser 43:05

5M ago43:05

43:05

From cinematography to the C-suite? Yes, you read that right. In this episode, TC Gill talks with Chris Geiser, CTO at DCG ONE, about an unconventional leadership journey that blends creativity, marketing, and tech strategy.If you’re into leadership lessons with a personal twist, this one’s for you.저자 IT Labs

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Episode 178: Creating Harmony in a Scaling Company Fueled by Acquisitions with Ed Federici 51:26

5M ago51:26

51:26

What happens when a company grows through acquisitions but wants to keep the startup spirit alive?In this episode, TC Gill sits down with Ed Frederici, CTO at Appfire, to explore how to build harmony in a scaling tech company, without crushing innovation. From preserving entrepreneurial culture to building strong, autonomous teams, this one’s packe…

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Episode 177: Building End to End Solutions for Health & Wellness Marketing with Oleg Korenfield 56:00

6M ago56:00

56:00

This week, TC Gill is joined by Oleg Korenfeld, CTO at CMI Media Group, to unpack how technology transforms health and wellness marketing. From traditional media to data-driven strategies, Oleg shares insights on building scalable solutions that deliver real campaign value.Expect stories on innovation, strategic tech adoption, and the evolving role…

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Episode 176: Why Purpose Beats Features: Designing for Outcomes with Drew Morrell 45:06

6M ago45:06

45:06

What makes great tech solutions truly effective? It’s not features, it’s outcomes. In this episode, TC Gill speaks with Drew Morrell, Head of Engineering at Workiva, about why user-centered design, agile thinking, and purposeful product development matter more than feature counts.Tune in for insights that cut through the noise and get to the core o…

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Episode 175: Growing as a Leader by Taking Calculated Risks with Eric Levin 55:42

7M ago55:42

55:42

In this episode, Eric Levin shares his journey to becoming CTO and how taking calculated risks shaped his leadership style, one that's purpose-driven and people-focused.Key takeaways:- Why calculated risks are essential for growth- How transparency can strengthen team dynamics- Why embracing hard, boring tasks matters for leadershipTune in for an h…

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Episode 174: The Power of Technology & AI with Joe Hsy 45:39

7M ago45:39

45:39

In this episode, Joe Hsy shares his approach to leading with innovation while balancing the benefits and risks of emerging tech—especially AI and data privacy. From scaling teams without micromanaging to aligning technology with real business value, Joe offers thoughtful insights for every tech leader.Key takeaways:- Ethical use of data and buildin…

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Episode 173: Systematizing Chaos - The CTO’s Playbook with Rob Molchon 48:38

8M ago48:38

48:38

How do tech leaders build scalable, sustainable systems without descending into chaos? Rob Molchon, CTO of Vestwell, shares his insights on structuring order in fast-moving tech environments. We also take a quick trip down memory lane to see just how far tech has come.Key takeaways from the podcast are: – Clear ownership ensures tasks get done with…

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Episode 172: Bridging the Gap Between Practical Engineering and Academia with Guy Yachdav 43:51

8M ago43:51

43:51

The tech sector can be highly specialized, especially for leaders in biotechnology. In this episode of CTO Confessions, host TC Gill chats with Guy Yachdav, Senior Director at Immunai. Tune in for insights into his leadership journey.Key takeaways from the podcast are: - Academia and tech intersect in exciting ways, like using machine learning to p…

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Episode 171: Servant Tech Leadership in the Realm of Collectors with Dan Van Tran 51:54

9M ago51:54

51:54

In this episode of CTO Confessions, Dan Van Tran shares how AI and tech power the authentication of collectibles, from cards to video games. We explore AI-driven pricing, scaling tech teams, and servant leadership in a unique industry.Key takeaways:- AI’s role in authenticating and valuing collectibles- Why emotions matter in price estimation- The …

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Episode 170: The Intersection of Emotion and Technology with Armen Berjikly 58:25

9M ago58:25

58:25

In this episode, we explore how emotions and technology work together to support employee growth. Tune in for a thoughtful discussion on what happens when technology meets emotions within the context of an organization.Key takeaways from the podcast are:- Aligning executive vision with employee execution fosters a unified direction.- Unstructured c…

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Episode 169: Designing Culture with Data at the Core with Matt Culver & Nomaan Ahmed 59:27

9M ago59:27

59:27

In this episode of CTO Confessions, TC Gill talks with engineering leaders Matt Culver & Nomaan Ahmed from Super.com about how data-driven decision-making shapes both engineering and company culture. They explore the role of data in leadership, team dynamics, and fostering a strong workplace culture.Key Takeaways:- Measuring the right things, even …

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Episode 168: What Makes a Great Tech Leader with Savas Karas 1:00:28

9M ago1:00:28

1:00:28

What makes a great tech leader? Savas Karas, CTO of CAPREIT, believes it starts with kindness, support, and open feedback loops. In this episode of CTO Confessions, he shares how fostering a strong culture helps teams stay motivated, aligned, and unafraid of challenges.Key takeaways from the podcast are: - A shared vision keeps teams focused on mea…

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Episode 167: The Complex Role of Leadership in Tech with Daniel Natic 43:07

9M ago43:07

43:07

In this episode of CTO Confessions, our host TC Gill and guest Daniel Natic dive into the complex role of leadership in tech, exploring the balance between managerial expertise and deep technical knowledge.Key takeaways from the podcast are: - Tech leaders must stay sharp. Keep up with trends, drive change, and understand your team’s decisions.- Tr…

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Episode 166: Strategies for Crafting Educational Solutions with Todd Ellermann 49:30

10M ago49:30

49:30

In this episode of CTO Confessions, we explore the dynamic relationship between educational standards, student engagement and the role of artificial intelligence. Listen to Todd Ellermann’s perspective on how these elements intersect and how they are shaping the future of EdTech.Key takeaways - EdTech companies must understand state-specific standa…

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Episode 165: How to Structure a Growing AI Company with Yaron Inger 48:08

10M ago48:08

48:08

On this episode of CTO Confessions, our host, TC Gill, is joined by Yaron Inger, Founder of Lightricks, who reveals the unfiltered story behind scaling an AI-driven company. Yaron shares the lessons learned during their growth, emphasizing the importance of managing cashflow, deciding to change their business model and navigating all major growth c…

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Episode 164: The Art of Organizational Transformation with Conlath Alcock 55:47

11M ago55:47

55:47

In this episode, our host, TC Gill, sits down with Conlath Alcock, Client CTO at T-Systems, to explore how understanding an organization’s current state and learning from the past can set the stage for a strong foundation and successful transformation.저자 IT Labs

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Episode 163: Humble Leadership in Practice with Tim Vasil 59:00

11M ago59:00

59:00

In this episode of CTO Confessions, host TC and Tim Vasil, CTO of LeanTaaS, explore humble leadership, discussing Tim’s journey from solo contributor to leading high-performing teams, his approach to feedback, building a human-centric culture, and knowing when to delegate.저자 IT Labs

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Episode 162: The Human Side Of Tech Leadership With Ivan Kusalic 46:37

11M ago46:37

46:37

In this episode of CTO Confessions, host TC Gill chats with Ivan Kusalic, CTO of green tech organization Enpal. Ivan’s diverse career has shaped his unique approach to tech leadership, rooted in curiosity, empathy, and a commitment to transparency and growth. He shares candid insights on leading in the renewable energy industry, inspiring tech lead…

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Episode 161: A Fintech CTO's Playbook for Driving Sustainable Innovation with Skyler Nesheim 56:36

12M ago56:36

56:36

In this episode, TC, our CTO Confessions host, and Skyler Nesheim, the CTO of Dwolla, discuss the strategies and mindsets that have propelled his career in the competitive and dynamic world of FinTech. A hidden world that we all use without knowing it.Key takeaways from the podcast are: Develop a framework to prioritize core, unique technology that…

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Episode 160: Confessions of a Tech Maverick with Jeremy Hodges 45:42

1y ago45:42

45:42

In this episode, we sit down with Jeremy Hodges, the CTO of Live Oak Bank, a digital-only small business bank. Jeremy shares his passion for customer-centric technology, his approach to balancing innovation and compliance, and the importance of addressing organizational weaknesses. Hear how Jeremy cascades his audacious vision throughout the compan…

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Episode 159: Cracking the Code of Tech Leadership with Farzona Pulatova 46:04

1y ago46:04

46:04

In this CTO confession session, we get insights from a VP of Engineering on Building High-Performing Teams. Join us as we dive into the mind of Farzona Pulatova, a seasoned tech leader who has navigated the industry’s complexities with grace and innovation.Key takeaways from the podcast are: - Farzona emphasizes the importance of creating a transpa…

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Episode 158: Confessions of a Tech Turnaround Titan with Misha Makara 54:11

1y ago54:11

54:11

In this session of CTO Confessions, we get an unvarnished look into the trials, tribulations, and hard-won wisdom of a tech leader who’s stepped into the arena of huge challenges and turned things around. Key takeaways from the podcast are:- Misha's key message is that mistakes and failures are inevitable, but they are also your greatest growth opp…

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Episode 157: Mastering the Art of Empowering High-Performing Teams with Catherine Miller 44:39

1y ago44:39

44:39

In this episode, our host, TC Gill sits down with Catherine Miller, the Chief Technology Officer of Flatiron Health. Catherine shares her passion for using data and technology to improve cancer treatment and drug development - a truly purposeful mission. We dive into Catherine's journey to the CTO role, the challenges of leading through different g…

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Episode 156: A Conversation on Metadata, Meaningful Work, and Embracing Change with Madalina Tanasie 49:03

1+ y ago49:03

49:03

Madalina Tanasie, CTO of Collibra, shares her insights on AI governance, data intelligence, and SaaS evolution. She highlights how advancements in AI have democratized technology and emphasizes the need for solid data governance. Tanasie also stresses the importance of meaningful work for engineers to drive innovation. Her perspectives offer valuab…

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Episode 155: Navigating the Responsible Development of LLMs with Vijay Karunamurthy 56:33

1+ y ago56:33

56:33

Vijay Karunamurthy, Field CTO at Scale AI, joins CTO Confessions to discuss his career in AI and the future of generative models. Vijay shares lessons from early neural network research and his time at YouTube, where he helped build recommendation systems. He explains his role translating customer needs to product roadmaps and ensuring ethical, tra…

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Episode 154: Architecting Success: Andreas Westendorpf's Vision of Tech as Business Backbone 37:14

1+ y ago37:14

37:14

In this insightful episode of CTO Confessions, listeners are treated to an in-depth exploration of technology and leadership through the experiences of Andreas Westendörpf, CTO of Emma. His journey, from a budding software engineer to an influential technology leader, is a central theme. The episode covers the crucial role of good architecture, wit…

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Episode 153: Eco-Innovation in Retail and the Path to Sustainable Business With Adam Siegel 31:44

2y ago31:44

31:44

TC Gill converses with Adam Siegel, co-founder of Recurate, a trailblazing retail tech startup. Siegel discusses his transformative journey from early computer enthusiasm to pioneering sustainable solutions in the retail sector. Listen in as he shares insights on creating a remote-first, mission-driven company culture, the challenges of balancing p…

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Episode 152: Breaking Codes and Building Teams With Rob Phillips 34:35

2y ago34:35

34:35

In this episode, TC engages with Rob Phillips, the Vice President of Software Engineering at UDig, a Richmond-based consulting company. Phillips delves into his journey from a passionate technologist in his youth to a seasoned leader in the tech industry. He shares valuable lessons on transitioning to senior leadership, the importance of understand…

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Episode 151: Leading with Insight: A Tech Odyssey With Robert Matsuoka 42:03

2y ago42:03

42:03

Join us in a compelling conversation with Robert Matsuoka, where he unveils his transformative journey from a tech-centric role to a strategic leadership position. In this episode of CTO Confessions, Robert delves into the art of delegation, the dynamics of building effective teams, and the criticality of nurturing talent. He also sheds light on ma…

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Episode 150: Crafting the Future: From Military Precision to Tech Vision With Alessio Garofalo 20:36

2y ago20:36

20:36

In this enlightening episode of CTO Confessions, Alessio Garofalo, the CIO/CTO of Oxagon at NEOM, delves deep into his multifaceted journey from the NATO military fields to the forefront of tech innovation. Drawing from his rich experiences in defense, tech giants like Amazon, and his entrepreneurial ventures, Alessio shares invaluable insights on …

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Episode 149: Mentorship, Systems Thinking, and Embracing the Unique in Tech With Michael Jones 30:30

2y ago30:30

30:30

Michael Jones is a seasoned technology leader with a rich history in steering digital transformation and scaling platform businesses, especially within PE and PLC landscapes. As Chief Technology Officer at uSwitch, Michael was pivotal in navigating the company through three significant exits: an MBO to LDC, a £190m trade sale to Zoopla, and a monum…

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Episode 148: Leading Beyond Titles: The Tech Visionary's Guide With Pierre Arman 32:38

2y ago32:38

32:38

In this episode of CTO Confessions, TC Gill welcomes Pierre Arman, a Partner – Global Tax SaaS Go-to-market Leader at EY, based in Dubai. Pierre dives deep into his role at EY, discussing the intricacies of tax technology, particularly in the realm of VAT and GST automation. As the conversation progresses, Pierre shares his insights on leadership, …

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Episode 147: The Future of Law: Automation and Expertise with Alex Bazin 25:32

2y ago25:32

25:32

In this episode of CTO Confessions, the conversation dives deep into the intersection of technology and the legal realm. Featuring insights from Alex Bazin, listeners are granted a look under the hood of the legal world, revealing the transformative effects of AI and tech innovations. Bazin's candid discussion offers listeners invaluable leadership…

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