Your Privacy

This site uses cookies to enhance your browsing experience and deliver personalized content. By continuing to use this site, you consent to our use of cookies.
COOKIE POLICY

Skip to main content
Back to insights

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

In this episode of CTO Confessions, Rob Phillips, the Vice President of Software Engineering at UDig, digs 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 PODCAST:

  • 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.

Digging In

  • Software Engineering

    Building a Consultant in the Trenches: How Playing Offensive Line Shaped My Consulting Career

    People often ask me the same question when they find out that I played college football: “Do you miss it?” On the surface, it’s a bad question with an obvious answer. Yes. However, if I give myself a minute to sit with that question, the answer is more nuanced. Yes, I miss playing football, but […]

  • Software Engineering

    Modernization That Sticks: Why Adoption, Not Just Architecture, Drives Success

    Modernizing a legacy sales platform in a large enterprise isn’t just a technical challenge, it’s a cultural and operational one. On a recent project with a Fortune 500 organization, several past attempts to replace the aging ERP system failed. Why? Because those efforts treated modernization as a software delivery exercise, not an adoption journey. When […]

  • Software Engineering

    Config 2025 Day Two Recap

    It felt as though Config 2025 ended as soon as it began, and I believe those of us that attended are all the better for it. By the end of the day, various inspirational and informative talks had been given by thought leaders and innovators in the product space. Between sessions, we had the opportunity […]

  • Software Engineering

    Inside Config 2025: What’s New in Figma

    Config 2025 kicked off with a bang on Day 1. Figma’s annual conference brings together designers, developers, and all those involved in the making of a product. The 2-day event has a stacked lineup of accomplished speakers ready to share their insights on the world of product building. At today’s opening keynote, the Figma team, […]

  • Software Engineering

    Choosing the Right Modernization Approach

    When organizations decide it’s time to modernize their technology infrastructure, choosing the right approach is crucial. Modernization isn’t merely a technical upgrade; it’s a strategic business move that significantly impacts growth, agility, and long-term success. Here’s how your company can effectively begin to select the best modernization strategy tailored to your goals and challenges. In […]

  • Software Engineering

    TAG Panel: Differentiate Your Customer Experience

    Join the CX and Product Management Societies to hear from our panel of Human-Centered Design experts on the business value of Agentic AI.