CTO Confessions Brought to you by IT Labs

CTO Confessions Brought to you by IT Labs

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.

Episodes

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

July 1, 2025 • 48 mins
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.
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Episode 179: From Cinematography to Strategic Marketing with Chris Geiser

June 24, 2025 • 43 mins
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.
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Episode 178: Creating Harmony in a Scaling Company Fueled by Acquisitions with Ed Federici

June 17, 2025 • 51 mins
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 packed with insight.
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Episode 177: Building End to End Solutions for Health & Wellness Marketing with Oleg Korenfield

June 10, 2025 • 56 mins
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 of marketing tech leaders.
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Episode 176: Why Purpose Beats Features: Designing for Outcomes with Drew Morrell

June 3, 2025 • 45 mins
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 of what product teams should focus on.
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Episode 175: Growing as a Leader by Taking Calculated Risks with Eric Levin

April 25, 2025 • 55 mins
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 leadership Tune in for an honest look at leadership in action. Important Risk Information: GCM Gros...
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Episode 174: The Power of Technology & AI with Joe Hsy

April 23, 2025 • 45 mins
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 building trust - Balancing AI’s potential with its risks - Leading without micromanaging...
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Episode 173: Systematizing Chaos - The CTO’s Playbook with Rob Molchon

March 26, 2025 • 48 mins
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 without constant oversight. – Strong foundations start with the right team in the righ...
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Episode 172: Bridging the Gap Between Practical Engineering and Academia with Guy Yachdav

March 20, 2025 • 43 mins
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 predict the unpredictable. - Leadership in both fields means helping individuals t...
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Episode 171: Servant Tech Leadership in the Realm of Collectors with Dan Van Tran

March 12, 2025 • 51 mins
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 challenges of scaling and leading with transparency Our Guest: Dan Van Tran L...
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Episode 170: The Intersection of Emotion and Technology with Armen Berjikly

March 6, 2025 • 58 mins
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 company survey language reveals emotions and intent, now decipherable with techno...
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Episode 169: Designing Culture with Data at the Core with Matt Culver & Nomaan Ahmed

February 19, 2025 • 59 mins
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 intangibles like happiness, helps build a strong organizational foundation. - Lead...
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Episode 168: What Makes a Great Tech Leader with Savas Karas

February 17, 2025 • 60 mins
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 meaningful goals. - Honest feedback leads to better decisions and stronger teams. - ...
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Episode 167: The Complex Role of Leadership in Tech with Daniel Natic

February 14, 2025 • 43 mins
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. - Treat tools as resources, set aside ego and focus on efficiency. - Challenge the s...
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Episode 166: Strategies for Crafting Educational Solutions with Todd Ellermann

February 7, 2025 • 49 mins
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 standards to succeed in U.S. K-12 education. - Engaging students used to TikTok-like co...
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Episode 165: How to Structure a Growing AI Company with Yaron Inger

January 23, 2025 • 48 mins
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 challenges while staying humane and making difficult decisions. Key takeaways from th...
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Episode 164: The Art of Organizational Transformation with Conlath Alcock

January 10, 2025 • 55 mins
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.
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Episode 163: Humble Leadership in Practice with Tim Vasil

December 27, 2024 • 59 mins
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.
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Episode 162: The Human Side Of Tech Leadership With Ivan Kusalic

December 20, 2024 • 46 mins
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 leaders of all levels. Key takeaways from the podcast are: Curiosity and empathy: Drive...
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Episode 161: A Fintech CTO's Playbook for Driving Sustainable Innovation with Skyler Nesheim

November 28, 2024 • 56 mins
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 drives your business while leveraging SaaS solutions for non-core needs to enabl...
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