CTO Confessions Brought to you by IT Labs

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)

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)

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.

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.

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)

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 insights and communication strategies. For those aspiring to climb the tech leadership ladder, this episode is packed with actionable advice, book recommendations, and perspectives that challenge conventional thinking. Key takeaways from the podcast are: - AI Streamlining - AI and technology are streamlining legal processes, enhancing accuracy and eliminating mundane tasks for junior staff. - Leadership Balance - Effective leadership balances trust with communication, avoiding micromanagement yet maintaining alignment. - Business First - Successful tech leadership prioritizes business needs, leveraging diverse tools to address specific challenges. Our Guest: Alex Bazin LinkedIn: https://www.linkedin.com/in/alex-bazin/ Website: https://www.lewissilkin.com/ Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

In this enlightening episode of CTO Confessions, TC Gill dives deep with Benny Keinan, VP of R&D at Windward, a tech veteran who's seen the evolution from Commodore gaming to leading the R&D at Windward, a maritime tech giant. Benny shares his passion for startups, the transformative power of APIs, and the importance of people in any tech journey. He emphasizes the strength in admitting what you don't know and the value of continuous learning. Join us as we sail through Benny's tech voyage and gather pearls of wisdom from his vast experience. Key takeaways from the podcast are: - The Power of APIs - how they can be really transformative, especially when they're flexible and powerful. They allow for innovation on top of innovation, opening up possibilities that even the creators hadn't imagined. - People Over Everything - The right team can make or break a project. It’s important for oneself to be surrounded with individuals who prioritize doing the right thing over politics or personal gain. - Strength in Admitting Ignorance - The power of saying "I don't know." Is immense. It's a sign of strength and confidence, paving the way for continuous learning and growth. Our Guest: Benny Keinan LinkedIn: https://www.linkedin.com/in/bkeinan/ Website: https://windward.ai/ Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

Jon Santee, Senior Director of Information Technology Operations at iRhythm Technologies, discusses the evolving concept of work-life flow, challenges of security in tech, and transitioning to a leadership role. Highlights include authentic leadership, ownership and humility, and knowing when to pivot.

In this episode of CTO Confessions, TC Gill welcomes Casper Rasmussen, CEO, CTO, and co-founder of Monta, a company building software for electric vehicle charging. Casper shares his journey from gaming to programming, his passion for road biking, and the evolution of his leadership style. The conversation dives into Monta's growth, the challenges of onboarding customers, and balancing current problems with future planning. Don’t miss out on Casper's insights into transitioning from a technical to a business leader and the importance of mentorship and asking questions! Key takeaways from the podcast are: - Emphasize Onboarding and Understand the Purpose: Properly onboard team members and ensure alignment with the company's mission. Understanding and communicating the core mission will align individual efforts with broader goals, fostering development and customer-centricity. - Iterate and Don’t Fear Failure: Don't wait for the "perfect" idea to start. Choose a market you believe in and begin iterating. Initial ideas may evolve, and that's normal. Embrace failures as learning opportunities and continuously adapt for success. - Balance and Charisma in Leadership: Cultivate charismatic leadership while recognizing the importance of work-life balance. The ability to "switch off" from work emphasizes the need for balance in leadership, contributing to sustained success and personal well-being. Our Guest: Casper H. Rasmussen LinkedIn: https://www.linkedin.com/in/casper-h-rasmussen-63b13922/ Website: https://monta.com/ Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)

In this captivating episode of CTO Confessions, host TC Gill sits down with Paul Dorney, CTO at BOSSCAT an inspiring tech leader, to delve into a remarkable journey filled with startup experiences, both challenging and triumphant. Paul's unwavering passion for problem-solving and servant leadership shines through as he shares invaluable insights on building a collaborative and inspiring work environment. Join them as they explore how Paul's team at BOSSCAT is revolutionizing the home ownership experience, leveraging technology to simplify maintenance and renovation tasks. Discover how they empower homeowners and contractors alike to save time and enhance productivity. Key takeaways: - Foster Open Communication: Cultivate a culture of open communication and idea sharing among team members. Stay connected to the team, encourage asking questions, and seek input from diverse perspectives to fuel innovation and creativity. - Cultivate Servant Leadership - Be a leader who values and supports the team's growth and excitement. Find intriguing projects and problems for them to tackle, fostering a collaborative and engaged environment. - Build Strong Foundations - Tackle growing pains in companies by implementing robust systems and thorough documentation. Maintain meeting discipline in Agile practices, focusing on concise and effective sessions for increased efficiency and communication. Our Guest: Paul Dorney LinkedIn: https://www.linkedin.com/in/pauldorney/ Website: https://bosscathome.com/ Intro and background music: Craig MacArthur - Power Shutoff (www.youtube.com/watch?v=x74iB_jtauw)