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 right positions. – Change is inevitable; managing it wisely is key. Our Guest: Rob Molcon LinkedIn: https://www.linkedin.com/in/rob-molchon-2160652/ Website: https://www.vestwell.com/ Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

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 transition, fostering self-leadership, and easing onboarding. - Rapid tech changes demand easy-to-adopt tools and opportunities for hands-on learning. Our Guest: Guy Yachdav LinkedIn: https://www.linkedin.com/in/gyachdav/ Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

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 LinkedIn: https://www.linkedin.com/in/dantran/ Website: https://www.collectors.com/ Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

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 technology. - Encouraging risk-taking empowers employees to experiment and grow. - Balancing uniqueness with shared experiences enhances relevance and appeal. Our Guest: Armen Berjikly LinkedIn: https://www.linkedin.com/in/armenb/ Website: https://www.betterup.com/ Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

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. - Leaders must listen, adapt, and embrace feedback to avoid blind spots and poor decisions. – Hiring for cultural alignment and fostering organic team connections strengthens the workplace. Success depends on a team-driven mindset, the ability to pivot, and a shared vision. Our Guests: Matt Culver & Nomaan Ahmed LinkedIn: https://www.linkedin.com/in/mattculver/ & https://www.linkedin.com/in/nomaanahmed/ Website: https://www.super.com/ Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

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. - Embracing failure encourages innovation and growth. - Kindness builds trust, the foundation of great leadership. Our Guest: Savas Karas LinkedIn: https://www.linkedin.com/in/savaskaras/ Website: https://www.capreit.com/ Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

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 status quo. Streamlining operations is key; change is inevitable, lead it. Our Guest: Daniel Natic LinkedIn: https://www.linkedin.com/in/daniel-natic/ Website: https://finquery.com/careers/ Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

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 content is a growing challenge. - AI in assessments sparks debates on integrity, skills mastery, and EdTech’s role. Our Guest: Todd Ellermann LinkedIn: https://www.linkedin.com/in/toddecus/ Website: https://www.imaginelearning.com/ Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

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 the podcast are: - Drive meaningful transformation by anchoring your efforts to clear, purpose-driven goals rather than change for its own sake. Prioritize initiatives that align with the business’s strategic vision to avoid unnecessary disruptions and ensure resources are allocated effectively. - Begin with a deep understanding of what the business needs to achieve. This clarity is much needed to inform the design and implementation of the supporting technology. - Examine past actions and learn from the experiences of other organizations. Many valuable insights are hidden in previous efforts, offering opportunities to drive transformational change by leveraging what has already been tried and tested. Our Guest: Yaron Inger LinkedIn: https://www.linkedin.com/in/yaroninger/ Website: https://www.lightricks.com/ Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

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.

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.

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 innovation and connection. Transparency: Encourage feedback and learning from mistakes. Tech alignment: Bridge tech and business effectively. Our Guest: Ivan Kusalic LinkedIn: https://www.linkedin.com/in/ikusalic/ Website: https://www.ivankusalic.com/ Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

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 enable responsible, sustainable growth. Utilize thoughtful questioning, such as "What problem are we solving?" and "What are we optimizing for?" to align teams, challenge assumptions, and drive better decision-making. Emphasize the value of documenting decisions, potential second-order effects, and leveraging mental models to improve collaboration, knowledge sharing, and future problem-solving abilities. Our Guest: Skyler Nesheim LinkedIn: Skyler Nesheim | LinkedIn Website: https://www.dwolla.com/ Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

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 company and empowers his teams to drive real impact. This is a must-listen for any tech leader looking to elevate their leadership game. Key takeaways from the podcast are: Jeremy’s unwavering focus on delivering technology that truly serves the customer’s needs is a masterclass in putting the user first. His team’s deep dive into the voice of customer research – a model all tech leaders should emulate. Navigating the complex regulatory landscape of banking is no easy feat, but Jeremy has found a way to enable his teams to innovate within the guardrails, keeping roadblocks at bay. Jeremy’s willingness to confront the “shadows” in his organization, both at the individual and team level, demonstrates a level of self-awareness and courage that all leaders should aspire to. Our Guest: Jeremy Hodges LinkedIn: https://www.linkedin.com/in/jrmyhdgs/ Website: http://www.jeremyhodges.com/ Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

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 transparent, empathetic work environment where teams are empowered to focus on what matters most, fostering high performance and innovation. - Farzona's insights on ruthless prioritization and embracing change equip leaders with strategies to navigate uncertainty, modernize systems, and position their organizations for sustainable growth. - Farzona's passion for mentoring women in tech and addressing systemic inequities inspires us to act and create a more inclusive, equitable future for underrepresented groups in the industry. Our Guest: Farzona Pulatova LinkedIn: Farzona Pulatova Website: https://www.earnest.com/ Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

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 opportunities. Lean into the lessons your missteps can teach you. - Misha emphasizes the critical importance of deeply understanding your customer's needs and designing intentional experiences rather than getting caught up in the latest shiny new technology. - Misha advocates for creating a work environment that encourages small, low-risk experiments to test hypotheses and iterate rapidly towards product-market fit. Failure is fuel for progress. Our Guest: Misha Makara LinkedIn: https://www.linkedin.com/in/mishamakara/ Website: https://www.mishamakara.com/ Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

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)

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)

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, transparent AI development. The conversation explores AI's potential to enhance understanding of complex issues through multimodal interfaces. Vijay offers advice on entrepreneurship and gaining new perspectives through direct conversations. Key takeaways from the podcast are: Fine-tuning AI models for real-time use cases like robots and self-driving cars will democratize access to AI. Leveraging direct conversations with customers, researchers, and experts will help you gain new perspectives and challenge assumptions. Testing is paramount as it will determine how safe, usable, and effective AI will be in the future. Our Guest: Vijay Karunamurthy LinkedIn: https://www.linkedin.com/in/vjkaruna/ Website: https://scale.com/ Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

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)