PwC’s Reggie Walker Shares Proven Strategies for Digital Transformation Success

“State the problem in words as clearly as possible.”

That dictum was among the many pieces of occasionally cryptic advice in the Oblique Strategies card deck that emerged in the 1970s. The product of music producer Brian Eno and collaborator Peter Schmidt, the strategies were created to help overcome creative roadblocks.

But the principle applies equally well to the vague and frequently enigmatic notion of digital transformation, which often poses its own challenges. While organizations of all stripes are spending vast sums on such efforts, few of them are resoundingly successful. A Forbes analysis shows that seven out of ten digital‑transformation initiatives fail to reach their goals. Yet, in the long run, organizations that do not transform risk becoming obsolete. Complicating matters further is the sheer number of initiatives that fall under the digital‑transformation rubric, ranging from AI to IoT to custom Salesforce applications.

One expert uniquely qualified to speak on these themes is Reggie Walker, PwC’s chief commercial officer. In an interview at the Salesforce Dreamforce event, Walker cut through the jargon to offer a clear perspective on digital transformation and the challenges that often accompany it.

Many vendors are promoting the concept of digital transformation. What sets PwC apart?

Walker: “We’ve been in business for a long time, and we’ve tackled large, challenging, transformative changes. Recently, we’ve driven a lot of transformative change within our own organization. It ultimately comes down to walking the talk. For us, that means learning through our actions internally and applying that experience to clients.”

In large‑scale digital transformations, Walker says there are a few key elements that often get overlooked:

• Executive sponsorship that is active, visible and engaged, not just a statement of support.
• Clear ownership of the digital‑transformation strategy, with senior leaders providing both sponsorship and adequate funding.
• Alignment of technology investments with the organization’s strategic vision.

“If you don’t see senior leaders fully engaged, that’s a major red flag,” Walker warns. “It’s a common pitfall when the initiative becomes a side project rather than a top‑down priority.”

Who sets the tone at PwC for internal digital transformation?

Walker: “It was our chairman, Bob Moritz. He not only set the vision but drove daily cadence updates. He would ask, ‘Where are we?’ ‘What do we need to do?’ and led by example.”

How do you drive that vision throughout the organization?

Walker: “You can’t buy technology for technology’s sake. Every investment must be tied to a specific business outcome and clearly communicated across the organization.”

He emphasizes the importance of defining roles so everyone understands how their work supports the strategic vision.

How should changes in strategic vision affect employees’ day‑to‑day work?

Walker: “Digital transformation isn’t just about a dedicated team; it’s about changing how all employees work. Upskilling is essential, but so is redefining what people should stop doing. Many organizations deploy new technology without removing legacy processes, which undermines adoption.”

He gives the example of replacing spreadsheet‑based workflows with AI. “If people can still use spreadsheets, they’ll revert to them.”

“PwC found that by upskilling staff and redesigning processes, we forced teams—including management—to abandon old habits,” Walker explains.

What other advice do you have for companies embarking on digital transformation?

Walker: “Make it fun. We use gamification to engage employees—point systems, contests, and even company‑wide challenges. For instance, we incentivized Salesforce usage by awarding points for specific actions and celebrated collective achievements with a week off on the Fourth of July.”

What does it mean to be a Salesforce leader at PwC?

Walker: “I wear two hats. I lead the U.S. marketing, sales and external communications organization and oversee our internal Salesforce implementation. Globally, I head the Salesforce practice, ensuring our capabilities align with the platform’s direction and enabling our clients to transform through Salesforce.”

“My dual perspective—both as an internal customer and as a consultant—gives me a unique advantage in advising clients.”

What are the biggest challenges that cause digital transformation initiatives to fail or stall?

Walker: “Each organization is different, but we’ve seen that many firms neglect the human side. PwC, with 250,000 employees worldwide, had to digitally train staff to stay competitive. We learned that being a world‑class provider internally is a prerequisite for helping clients excel.”

He concludes: “Successful transformation starts with an organization that has already transformed itself.”

— End of conversation —