
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.
Latest episodes

Oct 2, 2024 • 45min
Episode 157: Mastering the Art of Empowering High-Performing Teams with Catherine Miller
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 growth phases, and her authentic, empowering approach to leadership. If you're an aspiring tech leader, get ready for insights that will inspire you to make a real difference.
Key takeaways from the podcast are:
Passion for using technology can be a huge driver in improving lives, especially when it comes to innovation in healthcare.
Exploring different ways to navigate the evolving challenges of leading through startup growth and into a mature enterprise, with a critical focus on technical debt management.
The gifts that a transparent leadership style gives to your team members. How it becomes a model for others to emulate, invites autonomy while also providing clear direction and constraints.
Our Guest: Catherine Miller
LinkedIn: https://www.linkedin.com/in/catherine-miller-0177142/
Website: https://flatiron.com/
Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

Aug 20, 2024 • 49min
Episode 156: A Conversation on Metadata, Meaningful Work, and Embracing Change with Madalina Tanasie
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 valuable guidance in navigating the tech industry's rapid changes.
Key takeaways from the podcast are:
Embrace change and new technologies. Stay ahead by welcoming advancements, especially AI. Instead of fearing it, integrate AI into your operations enthusiastically and make it a core part of your strategy.
Connect work to meaningful outcomes. Ignite passion in your leadership and team. Ensure that engineering work is tied to meaningful customer results, keeping your engineers motivated and engaged.
Accept failure as part of the process. Focus on moving forward and view failure as a learning opportunity. Embrace setbacks as part of the journey to continuous improvement and problem-solving.
Our Guest: Madalina Tanasie
LinkedIn: https://www.linkedin.com/in/madalina-tanasie/
Website: https://www.collibra.com/
Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

Mar 28, 2024 • 57min
Episode 155: Navigating the Responsible Development of LLMs with Vijay Karunamurthy
Vijay Karunamurthy, Field CTO at Scale AI, brings a wealth of experience from his work on AI and recommendation systems at YouTube. He discusses the future of generative models and the importance of ethical AI development. Key highlights include the necessity of fine-tuning models for real-time applications and the value of direct conversations in gaining fresh insights. Vijay also stresses that robust testing is crucial for ensuring AI systems are safe and effective. Lastly, he reflects on the evolving implications of AI sentience in society.

Feb 26, 2024 • 37min
Episode 154: Architecting Success: Andreas Westendorpf's Vision of Tech as Business Backbone
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, with a focus on the MACH Alliance's contributions to e-commerce. It delves into the significant impact of organizational structure on technology, advocating for empowered, interdisciplinary product teams. Additionally, the episode sheds light on topics like technical debt and the essence of software development, all while underscoring the necessity of empathy in the tech industry.
Key takeaways from the podcast are:
- Empathy is Key in Bridging Technology and Business - Mutual understanding between technical and non-technical teams is crucial for effective collaboration and problem-solving.
- Organizational Dynamics Shape Software Development - The structure of an organization significantly influences its software architecture. Implementing effective team structures and interdisciplinary approaches can lead to more innovative and efficient product development.
- Continuous Learning and Community Engagement are Essential - Engaging with peer networks, podcasts, and tech blogs is vital for staying updated and tackling the complexities of technology leadership.
Our Guest: Andreas Westendörpf
LinkedIn: https://www.linkedin.com/in/westendoerpf/
Website: https://team.emma-sleep.com/
Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

Dec 20, 2023 • 32min
Episode 153: Eco-Innovation in Retail and the Path to Sustainable Business With Adam Siegel
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 product development with market demand, and his unique approach to tech leadership in the dynamic startup world.
Key takeaways from the podcast are:
- Leadership by Example and Service - The effectiveness of leading through personal involvement and prioritizing team support and empowerment.
- Adapting in the Startup Ecosystem - Strategies for managing rapid changes, focusing product development, and keeping teams motivated amidst the unique challenges of startup environments.
- Harmonizing Sustainability with Business Objectives - The importance of integrating sustainable practices into business models to create a beneficial impact on both the environment and the retail industry.
Our Guest: Adam Siegel
LinkedIn: https://www.linkedin.com/in/adammsiegel/
Website: https://www.recurate.com/
Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

Dec 6, 2023 • 35min
Episode 152: Breaking Codes and Building Teams With Rob Phillips
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 understanding and articulating company problems, and the art of empowering teams for high performance. The conversation also covers the challenges of remote leadership, the balance between data-driven insights and business goals, and the importance of hiring competent team members. With a blend of personal anecdotes and professional wisdom, this episode is a must-listen for leaders and aspiring leaders.
Key takeaways from the podcast are:
- Doer to Strategist Shift: Embrace the shift from task execution to strategic thinking and decision-making, focusing on broader organizational challenges.
- Fostering Innovation and Safety: Create a culture where experimentation is encouraged and learning from failures is valued, promoting innovation and adaptability.
- Data and Agility Balance: Achieve a balance between data-driven insights and organizational agility, making informed yet swift decisions in line with company goals.
Our Guest: Rob Phillips
LinkedIn: https://www.linkedin.com/in/rophilli/
Website: https://www.udig.com/
Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

Nov 22, 2023 • 42min
Episode 151: Leading with Insight: A Tech Odyssey With Robert Matsuoka
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 managing remote teams and establishing meaningful rituals in today's distributed work environments. Packed with practical insights, this episode is a must-listen for those navigating the intricate balance between technology and leadership.
Key takeaways from the podcast are:
- Leadership Over Technical Expertise: Matsuoka emphasizes that being a tech leader is more about leadership skills than technical prowess. He acknowledges the importance of having a solid technical foundation but stresses that the primary role of a tech leader is to guide, inspire, and manage their team effectively, rather than being the most technically proficient person in the room.
- The Art of Delegation and Organizational Building: A significant part of Matsuoka's leadership philosophy revolves around effective delegation and organizational structuring. He highlights the importance of understanding team dynamics, recognizing the varying levels of talent within a team, and strategically delegating tasks to ensure optimal productivity and growth for both individuals and the organization.
- Adapting to Remote Work and Cultivating Culture: Matsuoka discusses the challenges and strategies of managing remote teams, emphasizing the need for creating new rituals and practices to maintain a strong organizational culture. He advocates for intentional interactions and structured meetups to foster collaboration and connection among team members spread across different geographies.
Our Guest: Robert Matsuoka
LinkedIn: https://www.linkedin.com/in/bobmatnyc/
Website: https://www.tripadvisor.com/
Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

Oct 4, 2023 • 21min
Episode 150: Crafting the Future: From Military Precision to Tech Vision With Alessio Garofalo
Alessio Garofalo, CIO/CTO of Oxagon at NEOM, shares insights on hands-on leadership, prioritizing core objectives and diverse team dynamics. Advice for aspiring tech leaders, books and movies for self-discovery, and reflections on writing a book and wishes for leadership and technology. Final key takeaways include being hands-on, focusing on what matters, finding complementary team members, and subscribing to CTO Confessions and IT Labs newsletter.

Sep 26, 2023 • 31min
Episode 149: Mentorship, Systems Thinking, and Embracing the Unique in Tech With Michael Jones
Tech leader Michael Jones discusses mentorship, systems thinking, and embracing uniqueness in tech. He shares his journey to tech leadership, his egalitarian leadership style, and the challenges tech leaders face. Explore the concept of systems thinking and the importance of embracing uniqueness in IT Labs services.

Sep 20, 2023 • 33min
Episode 148: Leading Beyond Titles: The Tech Visionary's Guide With Pierre Arman
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, the importance of authenticity, and the challenges and rewards that come with leading a team. With a passion for practical solutions through technology, Pierre emphasizes the significance of being proactive, taking risks, and the profound satisfaction of seeing team members succeed.
Key takeaways from the podcast are:
- Leadership is an Attitude - Leadership isn't about titles but is fundamentally an attitude. True leaders fill gaps, take initiative, and are proactive.
- Value of Authenticity - Being genuine and consistent in leadership builds trust. Leaders should be ready to give credit and take blame.
- Nurturing a Team's Growth - Despite challenges, the satisfaction of seeing team members succeed is unmatched. Most will reciprocate trust and guidance tenfold.
Our Guest: Pierre Arman
LinkedIn: https://www.linkedin.com/in/pierrearman-saas-leader/
Website: https://www.ey.com/
Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)