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

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

  • Digital Products

    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, […]

  • Digital Products

    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 […]

  • Digital Products

    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.

  • Digital Products

    The Bloated SaaS Era: Paying More for Less While Businesses Wait

    SaaS was supposed to make business faster, smarter, and more efficient. Instead, it’s become bloated, expensive, and painfully slow to change. The platforms we rely on—Salesforce, Workday, SAP, and others—haven’t truly innovated in years. Yet, they demand massive investments in re-implementation, process re-engineering, and data migration just to keep up. It’s time to ask: Are […]

  • Digital Products

    Reid Braswell Joins UDig as Vice President, Software Engineering

    UDig is proud to welcome Reid Braswell as our new Vice President of Software Engineering. With over 13 years of experience in technology consulting, Reid brings deep expertise in digital transformation, modern software engineering, and client-focused solutions. His leadership and passion for solving complex challenges make him an exceptional addition to the UDig team. Reid’s […]

  • Digital Products

    Energy 2025 – Expansion of Fossil Fuels or Carbon Reduction?

    Now that the election is behind us, we have an opportunity to anticipate the possible effects on the energy industry under this new administration. What strategies will be impacted? What will remain the same? What opportunities can we take advantage of in 2025? This blog is meant to dig into these questions and provide some […]