Why Digital Transformation Fails (and How to Fix It): Foundations Over Flash 

Digital transformation is one of those buzzwords that gets tossed around in boardrooms, strategy decks, and investor updates. But for many organizations, the actual experience of digital transformation is far messier—and far more difficult—than the promise of modernizing operations with the latest technology. 

Brittany Greenfield, CEO and Founder of Wabbi, recently unpacked this reality on the Digital Shifts aka Corporate Evolution Tales podcast. Her core message? Successful transformation doesn’t start with tools. It starts with people, processes, and a mindset shift. 

Step One: Start with People and Processes 

Too often, digital transformation efforts are technology-first. A new platform is purchased, a pilot program is rushed out, and leaders expect immediate results. But without aligning the people responsible for executing and maintaining these systems—and the processes they follow—those tools often end up underutilized, misconfigured, or even abandoned. 

🔹 This is especially true in Dev Sec Ops and AppSec, where integration without clear ownership or process alignment leads to security becoming a bottleneck instead of a built-in enabler. 

Transformation needs to begin with a clear understanding of how teams operate today, what workflows exist, and where the real friction points are. Without this context, even the most advanced tool can’t solve the right problem. It just adds another layer of complexity. 

Brittany referred to this as the “shiny object syndrome”—a trap where organizations chase the newest tech trend without first doing the foundational work. This not only slows progress but creates disillusionment across teams when the expected gains don’t materialize. 

Step Two: Embrace the Phases (Including the Hard Ones) 

Digital transformation isn’t a sprint. It’s a phased journey—and every phase has its own challenges. The early stages are often filled with energy and enthusiasm. Teams are excited about moving forward, modernizing, and innovating. 

But that momentum can quickly fade when the hard work begins. Integrating new systems, retraining teams, reworking legacy processes—this is where many initiatives stall. Brittany called this the “trough of despair,” a period where the challenges start to feel overwhelming and the shine wears off. 

🔹 For AppSec and Dev Sec Ops, this is when development and security teams can become misaligned, especially if secure coding practices aren’t embedded into the SDLC from the start. 

Organizations that succeed are the ones that expect this phase and prepare for it. They treat transformation as a long-term initiative, not a one-time project. Leaders remain committed through the setbacks and keep teams aligned around the end goal—even when it gets tough. 

Step Three: Build for Ongoing Change, Not a Final State 

Perhaps the most important shift organizations must make is seeing digital transformation not as an endpoint, but as an ongoing capability. There’s no “done” in transformation—just a constant cycle of improvement. 

To stay competitive, companies need to be able to evolve continuously. That means being willing to phase out old systems, revisit processes, and reinvest in the next generation of technology—even if the current one hasn’t “expired” yet. 

As Brittany noted, “You have to be willing to draw down on the old thing to invest in the new thing.” Organizations that embrace this mindset create a culture of adaptability and innovation, rather than one of maintenance and stagnation. 

🔹 This principle is fundamental to mature DevSecOps: continuous improvement in secure development practices, tooling, and team collaboration—not one-and-done implementations. 

Step Four: Don’t Skip the Foundation 

Imagine building a skyscraper without pouring a proper foundation. It might stand for a while—but eventually, cracks will show. The same is true for digital transformation. A strategy built on unaligned teams, outdated processes, or fragmented systems will eventually crumble under the weight of new technologies. 

Before investing in the next big tool, organizations should take a hard look at their internal landscape. Are your people empowered and trained? Are your processes consistent and scalable? Is your data structured and trustworthy? 

🔹 For DevSecOps success, that foundation must include secure development training, consistent risk management workflows, and centralized AppSec orchestration—not just tools plugged into pipelines. 

Only when these questions are answered with confidence does it make sense to add new technology into the mix. 

The Bottom Line: 

Digital transformation is a marathon, not a magic trick. Without a strong foundation—people, processes, and the willingness to evolve—technology alone won’t deliver meaningful or sustainable change. 

🔹 But when organizations embed DevSecOps and AppSec practices into their digital strategies, transformation becomes more than a project. It becomes a secure, scalable, and competitive advantage. 

🎧 Listen to Brittany’s full conversation on the Digital Shifts podcast for more real-world lessons on what it takes to lead successful change.