The Future Of Digital Transformation Leadership
Bill Hineline is Field CTO for Chronosphere and previously led observability for United Airlines.
For years, the conversation about digital leadership has focused on one question: Should CIOs become chief digital officers (CDOs)? The argument was simple—businesses needed a leader to drive digital transformation, and many saw the CDO role as the natural evolution of the CIO.
But that debate misses the bigger picture. The real challenge isn’t about job titles—it’s about impact. Businesses don’t just need technology leaders—they need leaders who can drive digital transformation, measure its success and continuously align technology with business objectives.
I’ve seen this shift firsthand. While working at a large Fortune 100 company, I watched us undergo a dramatic transformation as we invested heavily in the cloud, AI and digital modernization. The goal wasn’t just modernization for the sake of technology—it was to enhance customer experience, improve loyalty, generate revenue and differentiate our products in a highly competitive industry.
With significant resources, we could invest in cutting-edge technology, automation and new digital experiences. But even at that scale, one of the biggest challenges wasn’t building new capabilities—it was ensuring those investments delivered measurable business value.
This transformation isn’t unique—in 2024, “90% of all organizations [were] undergoing some kind of digital transformation.” Global investment in digital transformation is projected to reach $3.9 trillion by 2027, underscoring the rapid pace at which businesses are adapting to the digital era.
Digital Transformation Looks Different At Every Scale
At the same time, I was leading a very different kind of digital transformation as board chair for a nonprofit crisis line serving runaway youth. The organization had a fraction of the budget and resources, yet its need for digital transformation was just as urgent.
When the pandemic hit, we had to make a rapid shift to remote operations to continue serving vulnerable youth. Unlike a Fortune 100 company, we didn’t have the luxury of multi-year digital roadmaps or enterprise-wide technology budgets. Every decision had to be highly strategic, maximizing efficiency while minimizing cost.
Our digital transformation focused on:
• Enabling remote services while maintaining operational continuity
• Reducing manual processes to increase efficiency with a small team
• Ensuring long-term sustainability with scalable, low-cost technology
Unlike large enterprises, where digital transformation is often about driving competitive advantage, for nonprofits and smaller organizations, it’s about survival and operational efficiency. Sixty-three percent of nonprofit leaders reported that Covid-19 accelerated their digital transformation efforts, forcing them to adapt quickly. Meanwhile, 45% of nonprofits reported improved service accessibility due to online operations.
Why Measuring Digital Investments Matters More Than Ever
Across both experiences, one thing was clear: Digital transformation is no longer optional, but without measurement, it’s impossible to prove its success.
For large enterprises, investments in the cloud, AI and automation must be continuously evaluated to ensure they align with business goals, whether that’s improving customer experience, increasing revenue or enhancing productivity. Observability plays a key role here, providing transparency into how technology investments perform during and after implementation.
For smaller organizations, measurement is just as critical. Every dollar spent on digital transformation must drive tangible impact, whether through cost savings, improved operational efficiency or expanding reach.
The difference isn’t whether digital transformation happens but how organizations approach it, execute it and measure success.
The Role Of Digital Technology Leadership In 2025 And Beyond
The businesses thriving today aren’t debating whether they need a CIO or CDO—they’re ensuring their digital technology leadership is fully integrated into corporate strategy.
This means:
• Proactively shaping business priorities, not just reacting to them
• Using measurement and transparency to validate digital investments
• Aligning digital technology initiatives with measurable business outcomes
• Ensuring technology is seen as a value generator, not a cost center
Leaders who succeed in this space aren’t defining their value by their job title—they’re proving their value through continuous alignment, measurement and business impact.
Final Thoughts
The conversation about CIOs versus CDOs is outdated—what matters now is who’s driving digital transformation effectively. Technology organizations that fail to prove the value of digital initiatives will find themselves back where they started: underfunded, undervalued and at risk of being outsourced. The companies that win in the digital age will be the ones whose digital technology leaders can tie innovation to business success—and measure it.
Is your digital technology leadership proving its value or just delivering projects?
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