As companies grapple with tighter budgets and shorter executive tenures, many flashy tech initiatives have failed to evolve into lasting business capabilities — prompting a rethink focused on speed, impact and alignment with core enterprise goals.
Whether this emerging reality is chalked up to factors like the President Donald Trump administration’s tariffs and economic uncertainty, or the specter of institutional inertia, for organizations finding themselves stuck in neutral, or even reverse, the imperative now is not to reignite transformation for transformation’s sake, but to architect an approach that ultimately can turn digital initiatives into digital and back-office capabilities.
A decade ago, digital transformation promised reinvention like new business models, superior customer experiences and operational efficiency. Initial momentum surged as organizations adopted cloud technologies, invested in analytics and embraced agile methodologies. But over time, the deepening levels of investment began to falter in back offices across the United States.
Many buzzy transformation initiatives can remain siloed, tech-led and detached from core business strategy. What often begins as a sprint toward modernization can deteriorate into an ongoing cycle of pilot programs, tool adoption and change management fatigue.
To bring the mojo back, companies and their C-suites can consider building not just for today’s challenges, but for tomorrow’s possibilities, in part by reorienting around capabilities, shortening time-to-outcome, and re-embedding digital into the organizational DNA.
Read also: For CFOs, the Tech Stack Is the Business Strategy
The New Decision Matrix Equals Time-to-Outcome Plus Business Value
The greatest barrier to progress isn’t always technology. It can often be the culture and structure of the enterprise itself. Many large organizations struggle with institutional inertia like rigid hierarchies, conflicting key performance indicators and entrenched workflows.
Add to those internal hurdles the external macro environment. New findings from the PYMNTS Intelligence May 2025 Certainty Project report revealed that 8 in 10 product leaders said tariffs have forced them to redirect their focus to short-term fixes over long-term strategies. This operating context frequently builds to a bottleneck.
Meanwhile, the turnover of chief information officers, chief digital officers and chief financial officers — many with tenures under three years — can disrupt continuity and weaken accountability.
At the same time, the capabilities of enterprise technology have never been advancing faster. The world is moving fast, which means enterprises need to keep up.
“This is an unprecedented time in history,” WEX Chief Digital Officer Karen Stroup told PYMNTS in April. “[AI] technology is evolving every six months. In general, organizations change on five- or six-year cycles. And so, the technology is outpacing us.”
“I think about it in terms of cost-benefit,” Stroup added. “If you’re going to experiment with agentic AI or any type of AI solutions, you want to focus on two things. One is the areas where you’re most likely to have success. And two, is there going to be a good return on that investment?”
See also: The M&A Files: You Just Had an Acquisition — Now What?
Reviving the Vision by Moving From Initiatives to Capabilities
The classic return-on-investment model in many ways may no longer suffice in today’s environment where agility and speed can make or break competitive advantage. A revised decision framework might include time-to-outcome (TTO), or how quickly the initiative can deliver a measurable result, and strategic value alignment (SVA), or how closely the initiative supports core business priorities, as key matrices.
Projects with shorter TTOs, for example, can build confidence and free up resources for longer-term bets. SVA projects that are tied to customer retention, cost reduction or regulatory compliance often score higher.
By plotting initiatives on a 2×2 matrix — short/long TTO versus high/low SVA — leaders can better allocate resources and sequence transformations logically. High SVA/short TTO efforts, like automating invoice processing or enhancing digital onboarding, can take precedence.
The PYMNTS Intelligence report “Smart Spending: How AI Is Transforming Financial Decision Making” found that 68% of CFOs are willing to invest in real-time spend visibility.
Another enabler of momentum can be taking a fresh look at the enterprise tech stack. Legacy systems are no longer just a technical liability — they are strategic impediments. A digital platform, in this context, isn’t just a tech solution — it’s a strategic foundation that supports continuous innovation. The magic lies not in the tools, but in the tenacity to use them wisely, combined with the clarity to measure what truly matters.
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