Enterprise software has become one of the most critical (and misunderstood) assets on a company’s balance sheet. It’s the nervous system of the organization, connecting finance, operations, sales, HR, and strategy.
Yet, in my years as an advisor and interim finance leader, I’ve seen how even the most sophisticated organizations can underestimate the role enterprise software plays in shaping financial outcomes. What I’ve seen most often is that companies struggle to pin down the real value of their systems. They know what they’ve spent, but not always what they’ve gained. I’ve watched software create tremendous efficiency, and I’ve also watched it quietly drain enterprise value when it’s misaligned, underused, or poorly implemented. The difference comes down to one thing: whether the investment is truly delivering on what the business needs.
That’s why it’s important to evaluate whether enterprise software is Relevant, Executable, Adoptable, and Lasting. This framework, born out of time in the trenches rather than theory, reflects what I’ve learned from seeing finance teams at every stage of transformation:
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Relevant
Does the software actually solve the business problem it was meant to address?
Software value isn’t what you buy—it’s what you can actually use. In technical accounting terms, enterprise software value often revolves around capitalized costs, impairment testing, or purchase price allocation. But in practice, the real question isn’t “what did we pay for it?” but “what does it enable us to do that we couldn’t before?”
I’ve joined companies that spent millions implementing ERP systems that never quite worked as intended. Data wasn’t clean, reporting was delayed, and finance teams still lived in spreadsheets. On paper, those systems looked like valuable assets. In reality, they were underperforming investments. The inverse is also true: I’ve seen leaner teams unlock enormous value from mid-tier software by optimizing workflows, training staff, and integrating across functions.
- Takeaway: Expand your definition of ROI. Don’t just look at cost or amortization. Ask whether people are actually using the system as intended, whether reporting has become faster or more accurate, and whether leadership has better data to make decisions.
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Executable
Can your organization realistically implement and sustain it?
Implementation risk is valuation risk. Software investments are often made with great intentions but unrealistic timelines. I’ve stepped into multiple interim leadership roles in the wake of major system implementations, and one pattern stands out: no matter how strong the software, its success hinges on execution and capacity.
The finance team is usually juggling month-end close, audits, and new reporting demands while learning a new system. Add in resource constraints or turnover, and you have the perfect storm for missed milestones—and value leakage. When implementation risk materializes, it doesn’t just delay progress; it changes value. Deferred integration, delayed reporting, and manual workarounds create inefficiencies that show up in EBITDA, working capital, and even investor confidence.
- Takeaway: Treat software implementation like any other capital investment. Build contingencies not just for cost overruns, but for the human bandwidth needed to handle day-to-day operations while the core team transitions, for validating data completeness and accuracy, and for post-launch support like training and documentation.
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Adoptable
Are people actually using it—and using it well?
Adoption determines impact, and a system that’s technically sound but culturally neglected can’t drive value. I’ve learned that the real value of enterprise software isn’t what you pay for—it’s what you can actually use. Remember, software is a catalyst, not a cure-all. The organizations that realize the greatest long-term value from their systems are those that invest in their people as much as their platforms.
There have been countless companies where millions were spent on a sleek new ERP, only for the team to retreat back to spreadsheets within months. The problem wasn’t the software, but the lack of buy-in, training, and ongoing reinforcement. The opposite happens, too—smaller organizations with limited resources make mid-tier systems feel world-class because they invested in user education, built champions within finance, and created habits around continuous improvement.
- Takeaway: Adoption doesn’t happen by decree; it happens through engagement. Build adoption plans that start early and continue long after go-live. Identify system advocates within teams, reinforce success stories, and align incentives so people see the system as a tool for empowerment.
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Lasting
Will it scale, evolve, and continue adding value over time?
True software value isn’t defined at implementation. Long-term software value grows only as fast as the organization’s capacity to evolve with it. Every company grows, restructures, and redefines priorities. The platforms that continue to deliver are those that are flexible enough to evolve alongside the business and are supported by teams that treat improvement as part of the job, not a project with an end date. Longevity requires both flexibility and discipline. A system that lasts is one that’s maintained, adapted, and actively led—because durability in finance technology is never an accident.
- Takeaway: Build a cadence for reviewing performance metrics, user feedback, and alignment with evolving goals. Prioritize software partners who keep their systems current and offer scalability without disruption.
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The Big Picture
In my experience, companies often focus too narrowly on the price tag of software instead of the value chain it supports. At WilliamsMarston, we believe enterprise transformation doesn’t have to come at the expense of control or confidence. Our advisors help CFOs and finance leaders bridge the gap between accounting precision and operational agility—so that investments in technology translate into measurable enterprise value. When implemented thoughtfully, enterprise software gives leadership confidence in the numbers, transparency into performance, and the agility to act on insights. Ultimately, enterprise software isn’t just a tool for finance. It’s a measure of how ready a company is for the future.
