4 min read
How Digital Masters Are Preparing for an AI-enabled Future
Philip Ideson : Updated on May 17, 2026
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“Digital masters aren’t just deploying technology. They’re changing the way procurement runs.” - Chris Riley, Partner - Supply Chain and Procurement, Deloitte
Expectations are rising across the business, AI is accelerating the pace of change, and the operating models that carried procurement through the last decade are starting to show their limitations.
What stood out to me in this conversation with Chris Riley, Ryan Flynn, and Jocelyn Mayfield from Deloitte is that the discussion has moved beyond whether AI matters. The answer to that has been obvious to everyone for some time now.
The unanswered question is how procurement leaders should think about redesigning their organizations to create value in an AI-enabled environment. Each team will need to answer that for themselves.
The encouraging part is that procurement has already made significant progress. As Ryan points out early in the discussion, procurement has earned a stronger and more strategic seat at the executive table in many organizations. Now, they have to figure out how to evolve without losing momentum.
Here, in Chris, Ryan, and Jocelyn’s own words, are some of the stand-out moments from our conversation.
Procurement’s Success Story Comes with a New Challenge
“We found quite a bit of success with procurement organizations. We’ve been talking for years about procurement getting a seat at the executive table, becoming more of a strategic part of the business, all these great things. And it seems like, to a large extent, we’ve arrived there. But then you have looming in the background this huge change and uncertainty being driven by AI.” - Ryan Flynn
I think Ryan framed this perfectly. It captures the anxiety many procurement leaders are feeling right now. For years, procurement worked to elevate their influence and prove their strategic value, and in many organizations, that progress is real.
The difficulty is that AI is introducing another wave of transformation. What I see among the most forward-thinking leaders is a willingness to stay uncomfortable. They recognize that previous successes do not guarantee future relevance. The organizations moving fastest are approaching AI with curiosity rather than defensiveness.
Operating Model Design Has Become a Leadership Issue
“The opportunities to add more value are rampant. The harder news story is that they aren’t ready to meet that challenge.” - Jocelyn Mayfield
This is one of the most honest observations in the conversation. Procurement has more access to data, more influence, and more opportunity than ever before. But many operating models were designed for a world centered around process execution and control.
As AI reduces the amount of manual and transactional work required, leaders are being forced to rethink how teams are structured, where value is created, and what skills matter most. Those are decisions that sit directly with human-led leadership, not tools or technology, but many are still struggling with readiness. Organizations know where they want to go, but they may still be trying to use structures and behaviors designed for a very different environment.
The Work Left Behind Will Become More Human
“The work that’s going to remain is going to get more human. Human with stakeholders, human with suppliers. How do we become that orchestrator of those conversations?” - Chris Riley
The value of the procurement skill set is shifting toward judgment, influence, interpretation, and relationship management. Those are all deeply human capabilities.
As more tactical activities become automated, procurement teams will spend less time processing and more time guiding decisions. That changes what leaders should prioritize when developing talent. Technical skills and digital fluency matter, but so does the ability to influence stakeholders, navigate ambiguity, and connect procurement outcomes to broader business priorities.
AI Should Support Better Decisions, Not Old Processes
“Don’t start with AI. Be really clear around what the key decisions are I need to be making as the organization, what do I want the humans to be doing, and really rethink the roles and the processes that we need in the future.” - Chris Riley
I strongly agree with Chris’s perspective here because too many transformation efforts still begin with the tool rather than the outcome. AI can absolutely improve speed and efficiency, but if organizations simply automate existing processes without questioning whether those processes still make sense, the impact will be limited.
Procurement Needs to Lead the Change
“If you wait for someone else in the organization and the executive team to define their new expectation of you and your team, you will have missed that chance to truly be that equal and key influencer at the table.” - Jocelyn Mayfield
This quote stands out because it captures the urgency of the moment. Procurement has spent years asking for greater influence and a stronger voice in enterprise strategy. AI creates an opportunity to redefine how the function contributes, but leadership teams will not wait indefinitely for procurement to decide what that future looks like.
The strongest CPOs I speak with are not waiting for perfect clarity before moving. They are experimenting, testing use cases, investing in talent, and learning in real time. There is risk in moving too slowly, especially when the pace of change across the enterprise is accelerating.
The Future Requires Different Skills and Different Measures
“If we are changing people’s performance management expectations and evaluating them differently and rewarding them differently for outcomes better connected to the new role, the higher value-add role, then I do think it changes the conversation.” - Jocelyn Mayfield
One of the hardest parts of transformation is that organizations often expect different outcomes while continuing to reward the same behaviors. Procurement is no exception. If teams are still measured primarily on transactional execution or traditional sourcing metrics, they will naturally gravitate back toward those activities. Real transformation requires a shift in what leaders value, what they reward, and how they define success. That cultural shift is often harder than implementing the technology itself.
As I reflect on this discussion, what stands out most is that procurement has reached another inflection point. The opportunity ahead is significant, but realizing it will require more than deploying AI tools. It will require procurement leaders to rethink operating models, redefine talent strategies, and become much more intentional about how they create value for the business.
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