Podcast: Breaking Codes and Building Teams

Breaking Codes and Building Teams with Rob Phillips


Mastering Strategic Thinking, Cultivating Experimentation, and Balancing Agility with Data

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. 

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“Understanding and articulating company problems is crucial. It’s not just about identifying issues, but also providing the next step towards their resolution. This ability is key for successful leadership transitions.”  

Rob Phillips

  • 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. 

TLDR: Straight to the point

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Podcast: Leading with Insight: A Tech Odyssey

Leading with Insight: A Tech Odyssey with Robert Matsuoka 


Exploring Robert’s Transformation from Tech Specialist to Visionary Leader

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. 

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Leadership comes first, then tech after that. It’s about being a leader first, with a solid foundation in tech, but not leading with the tech.  

Robert Matsuoka

  • 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.  

TLDR: Straight to the point

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Podcast: Crafting the Future: From Military Precision to Tech Vision

Crafting the Future: From Military Precision to Tech Vision with Alessio Garofalo


Discovering Leadership, Innovation, and the Power of Hands-On Experience

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 leadership, adaptability, and the rapid evolution of technology.

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I think leaders need to be like water, you need to be flexible, you need to adapt to different people that are working with you and, and being humble in a way to adapt yourself to the environment that you have around.  

Alessio Garofalo

  • Hands-On Leadership – Delving one level deeper and understanding the intricacies of tasks can foster better decision-making and team understanding. 
  • Focus on What Matters – In the whirlwind of innovation and tasks, prioritizing core objectives and reducing dependencies can lead to more impactful results. 
  • Complementary Team Dynamics – Instead of seeking like-minded individuals, finding team members with diverse skills and perspectives can lead to a more holistic and effective team. 

TLDR: Straight to the point

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How to Create a Winning Team

How to Create a Winning Team

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Swathi Young

Swathi Young

CTO at Integrity Management Services

Swathi is proud of the fact that she has held every possible position in the technology world. From Software developer, Technology Analyst, Engineer, Product Manager, Director of Engineering, and, more recently, CTO.

At the heart of every role for Swathi is joining the dots’ between the business problem and technology solution. She has helped numerous companies launch new technology products, mentored startups to find product-market fit, and scaled products for the enterprise. And one of the things that become evident in conversations with her is she is a huge proponent of the ‘Lean Startup Methodology.’

Having worked across various industries, including supply chain, Hi-Tech, transportation, finance, and geographies – Belgium, India, and the United States, she has served as a fuel to implement innovative solutions.

“[There is a] convergence of multiple technologies, […] unprecedented in the history of humans.”

As a technologist and life long learner, Swathi entered the world of AI/ML (machine learning), helping organizations with their AI strategy to make sense of their data to drive innovative solutions.

She believes that the intersection of Artificial Intelligence and humanities is essential to focus on as we lay the foundation of AI applications for future generations. Her work currently gravitates around researching the ethical implications of partial data in AI alongside working with the US state department, creating a framework for ethics in AI. 

She is a proud Women in AI crusader, STEM for girls supporter, I aim to bring diversity to the technology table. Building a thriving community of over 2000 members – “DC emerging technologies” with the sole purpose of educating and having conversations around how emerging technologies like Blockchain and AI, can be used by organizations to increase productivity growth.

Swathi is also the Co-author of AI Playbook for federal agencies – https://ai-working-group.github.io/ai-playbook/

Currently leading the Ethical Applications of AI framework for US federal agencies (a collaborative effort between government, industry, and academia)

Swathi’s specialties include:

  • Ethics/Bias in AI
  • Humanizing Big data
  • AI solutions, DataScience
  • Machine Learning
  • Product Management
  • Digital Strategy Web and Mobile Applications (iOS and Android)
  • Agile and Continuous Delivery(DevOps)
  • Public/Private/Hybrid Clouds
  • Product Development
  • Digital transformation

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Eugene Kovshilovsky

Eugene Kovshilovsky

Sr. Vice President of Software Engineering at CarParts.com

Eugene Kovshilovsky is a high energy leader who creates scalable, high-profile, and quality technology solutions thru a sustainable and goal-driven application development process. Highly entrepreneurial with a reputation for finding unique right-fit solutions to hard to solve problems and achieving exceptional results. Can thrive in all environments from startups to large organizations and everything in-between.

Some of his previous positions are: Vice President Of Engineering at EnterpriseAlumni, CTO at SmartCSM, Director of Engineering at Media Temple a GoDaddy company, Vice President of Engineering at HiveWind, Follow him on LinkedIn and Twitter.

“Don’t be afraid to make mistakes and choosing the wrong path, but the right path for the right time. You may decide that you want to build something because you think that it’s the right approach, and then as the industry or your market matures, you may decide that you want to swap it out for something more robust.”

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