CIO Panel: How Technology Leaders Are Powering Retail’s Planning Transformation

When retail CIOs and CDOs talk digital transformation, they don’t speak in theory—they speak from the frontlines. For Brian King, former EVP and CIO at T-Mobile, and JJ Van Oosten, a veteran digital transformation leader, the journey from legacy to leadership is one marked by vision, persistence, and a deep understanding of both data and people.

In a recent panel discussion, the two reflected on the evolution of the CIO/CDO role, the impact of AI, and the real-world lessons they’ve learned while leading transformation at scale. Their stories reveal not just the technical complexity of modern retail planning but the cultural and leadership shifts that define successful transformation.

Rethinking the Chief Information & Chief Digital Officer roles

The technology leader’s seat at the table has changed radically. Where CIOs once focused on operational stability, today’s CIOs are expected to help drive strategy, identify growth opportunities, and shape the business roadmap.

JJ, a five-time transformation leader, put it simply: “The days of CIOs taking orders are gone.” Today, they’re equal parts technology steward, business strategist, and cultural change agent. He pointed to Decathlon’s CEO, formerly the CDO of IKEA, as a signal of how the C-suite is evolving—technology leaders are increasingly stepping into CEO roles because they understand the full business landscape.

Brian echoed that sentiment, describing the CIO remit as “a third operations, a third transformation, and a third strategy.” It’s a balancing act that requires deep cross-functional collaboration, not just with IT or finance, but with every part of the business. And to deliver real impact, CIOs must also help shape and sometimes challenge priorities, educating business stakeholders on what’s possible and where the real tradeoffs lie.

How to begin

Both leaders emphasized that successful transformation begins with alignment. JJ described the value of objective key results (OKRs) and clearly defined KPIs, calling them “a North Star” that cuts through noise and keeps teams focused on impact. Brian added that when IT is tightly aligned with business goals, it shows in the way stakeholders talk about outcomes, not just tools.

“Have your business partners present IT progress in a QBR,” he said. “It’s the ultimate proof that what you’re building actually matters to them.”

But alignment also requires trust. For JJ, that starts with understanding the P&L—knowing where value is created, not just where costs reside. “It's difficult to increase sales,” he noted. “But if you understand where growth comes from, you can design technology to amplify it.”

The role of AI: promise meets pragmatism

Of course, no discussion of modern transformation is complete without discussing AI. JJ and Brian both expressed optimism and realism.

JJ described touchless forecasting, autonomous replenishment, and closed-loop planning as not just possible, but necessary. The goal isn’t to replace people, but to free them.

Brian agreed, adding that identity is often wrapped up in legacy processes. “When you automate something someone’s done for 15 years, you have to show them how their time is now spent on higher-value work,” he said. “That’s change management.”

GenAI and natural language interfaces also came up as accessibility enablers. When planning and analysis can happen through conversation (not just code) adoption increases. But Brian stressed the importance of pairing GenAI with more mature ML solutions to ensure scale and reliability.

Data strategy: Meccano or Lego?

Perhaps the most memorable metaphor of the discussion came when JJ compared data architecture choices to childhood toys. “You can build with Meccano or Lego,” he said. “But once you choose, you need to educate your colleagues and focus on the use cases that matter most.”

For example, in retail, markdown optimization might start with air conditioners and summer inventory, but once built, that logic can apply to thousands of SKUs. “Reusable data assets are like Lego blocks,” JJ said. “Built right, they can be applied across pricing, planning, forecasting, and more.”

Brian agreed - when data is unified and structured for reuse, teams can operate faster and smarter, without duplicating effort.

What makes transformation stick?

With all this innovation, one question remained: what separates projects that scale from those that stall?

JJ didn’t hesitate. “Start with the chairman. If you don’t have top-down commitment, walk away.” Without sustained sponsorship from the CEO and board, even the best-designed plans can fail.

He also described the shift to a product mindset, one where cross-functional teams are empowered to innovate and solve problems autonomously. It’s not always easy, especially in cultures that prize control and certainty. But for JJ, the rewards are clear: “You become a servant leader. Your job is to remove roadblocks so others can thrive.”

Brian added that when transformation is done right, it becomes self-sustaining. “Continuous improvement beats launch-and-leave,” he said. “You don’t want a one-time success—you want a long-term advantage.”

Final thoughts

In closing, JJ reflected on what separates strong CIOs from great ones. “They’re visionary, empathetic, and brave,” he said. “They’re not just implementing technology—they’re reshaping what’s possible.”

Brian echoed that sentiment, adding that the most successful technology leaders don’t just adapt to change, they inspire it. From architecture to empowerment, from AI to alignment, transformation today is a team sport. And CIOs, more than ever, are playing offense.

o9 Solutions Named a Leader in 2025 Gartner® Magic Quadrant™

For the third time, o9 has been named a Leader in the Gartner® Magic Quadrant™ for Supply Chain Planning Solutions. Learn why and how our AI-powered platform is transforming supply chain planning for global enterprises.

Download now

Learn more