Middling with IT: Why CFOs Are Tired of Empty Promises

“Middling with IT” is a series from Safebox LLC focused on helping middle-market companies with $100MM to $1B in revenue leverage IT to drive scalability, profitability, and cost controls.

The Brutal Truth: CFOs Are Done with IT’s Overpromises

It’s that time of year again. Greg, the CFO, sits through yet another overhyped pitch from his CIO about “digital transformation”—AI, automation, a new data infrastructure. It’s the same story: lots of new shiny tech objects, big ideas championed by Silicon Valley, unclear business value, skittish business team support, and poor execution. Greg is fed up. Every year, it’s the same thing: bold ideas that rarely, if ever, enable revenue growth or cost reductions. 

Where are the results? 

Where are the savings? 

Where is the impact on margins? 

The truth? IT’s ambitions are disconnected from financial reality. Greg’s job is to protect EBITDA, and IT spending is bleeding cash. CFOs aren’t looking for feel-good stories—they need measurable results that drive profitability and efficiency. Too often, IT leaders chase the latest tech trends without any clear plan to drive revenue or cut costs. They roll out new tools and expect a pat on the back, but from the CFO’s chair, it’s just another hit to OpEx. Especially in private equity backed companies, this is a death sentence. If any investment doesn’t increase valuation or improve margins, it’s a wasted investment. 

How IT Leaders Can Win Over CFOs: Talk more about ROI and less about AI

If IT wants to win CFOs over, they need to stop talking tech and start talking money. Greg doesn’t care about AI unless it’s going to cut costs, drive revenue, or streamline operations. The message is simple: Show me the impact on the bottom line, or don’t show up with a new ask.

To get CFOs on board, IT needs to drop the jargon and present a business case that hits hard, and to do that, IT can’t work in a silo. IT leaders must ensure that the financial data in their proposals comes from a P&L owner, not just IT. Any project aimed at reducing costs, increasing revenue, or improving margins needs to have its numbers validated by a P&L leader who understands the direct impact on the bottom line. Both the head of IT and the P&L owner must be jointly responsible and accountable for delivering what was promised in the business case that justified the funding. Setting clear success criteria before the investment is made and tracking them together ensures that the results are grounded in financial reality, not just IT-driven projections.

Here’s how to do it:

1. Define the Goal: Are you cutting costs? Boosting revenue? Reducing risk? Get specific.
2. Show Financial Impact: Give them real numbers. How will this save money or drive revenue? Use metrics like operational cost reductions or profit margins.
3. Set Success Metrics That Matter: Focus on cost-per-transaction, time-to-value, or other Key Performance Indicators (KPIs) that CFOs care about.
4. Give a Timeline for ROI: CFOs want to know when they’ll see results. Lay out a clear path for ROI in both the short and long term.
5. Own the Risk: Show how your plan mitigates risks — whether it’s cybersecurity, operational bottlenecks, or financial exposure.
6. Deliver Accountability: CFOs value ongoing transparency. Provide regular progress reports with concrete results so they know IT is delivering as promised.

Moving Forward with Safebox: Where IT Delivers

At Safebox, we help middle-market companies implement IT strategies that drive business results. We make sure IT is lean, scalable, and aligned with financial goals and business strategy. Our approach drives efficiency, boosts margins, and keeps your technology in sync with your business needs.

We focus on three core principles:

1. Hands-On Execution: Safebox gets involved where others fail. We step into the toughest IT challenges—whether it’s a stalled project, a failing system, or a bloated budget—and deliver fast, measurable results. Our approach is action-driven, getting projects back on track and delivering ROI where others couldn’t.
2. Measurable Success: Every solution we build is tied to a measurable financial outcome. We cut costs, enable productivity improvements and revenue growth, and deliver real impact on the bottom line without compromising quality.
3. Collaboration: We work with both IT and finance teams to make sure that every project aligns with financial goals and delivers measurable returns.

If you’re ready to stop wasting money on IT that doesn’t deliver, Safebox can help you unlock the real potential of your IT investments. Let’s get started. Contact us today.