It’s a question that every board of directors should be asking, of leaders of organizations large and small.
And it’s a question that too many CEOs can’t answer with conviction.
Who in the organization is thinking strategically about the potential of various technologies for them?
In an era when artificial intelligence can draft a marketing plan, predict customer churn, and even make hiring recommendations before your morning coffee… who’s in your corner thinking not about the technology you have – but the technology you should have?
The answer, for far too many organizations, is no one… And that’s an incredibly dangerous place to be.
The New Strategic Imperative
The pace of change in technology has always been brisk. But in the past three years, it has shifted from brisk to blistering. AI breakthroughs that once seemed decades away are being commercialized in months. Cloud platforms that were once the frontier are now the minimum. And in almost every industry, competitors are not just using technology… They are reinventing themselves through it.
For midsize companies, this isn’t an abstract conversation about “innovation” or “digital transformation.” It’s about survival and growth. In many industries, the companies that will lead five years from now are already laying the digital and AI groundwork today.
If no one inside, or closely aligned to, your organization is scanning that horizon, you’re playing defense in a game where offense wins.
The Risk/Reward Equation Has Shifted
For decades, technology investments for midsize companies were largely framed around efficiency: better ERP systems, faster networks, incremental automation. The risk of falling behind was real, but it was incremental.
Today’s technology stakes are different. AI, machine learning, advanced analytics, large language models, and integrated digital ecosystems aren’t just improvements—they’re multipliers. They have the potential to reshape cost structures, unlock new revenue streams, personalize customer experiences, and open markets you couldn’t enter before.
That’s the reward side of the ledger.
The risk side is equally stark. AI models trained on bad data can drive bad decisions at scale. Cybersecurity threats can escalate from nuisance to existential in hours. And the cost of doing nothing—of sticking with “business as usual” while competitors embrace transformation—can quietly erode your market position until it’s too late to catch up.
This is not a climate where you can delegate “keeping the lights on” to an IT director and call it a day.
The Talent Gap at the Top
Here’s the uncomfortable truth: most midsize companies don’t have a C-level technology leader thinking strategically about IT and AI. Those that do often have someone whose background is rooted in infrastructure, security, or operations—a critical skill set, but not the same as a forward-looking strategist who sees the business through both a commercial and technological lens.
As a result, conversations about AI, automation, or new digital platforms often never make it to the boardroom. Or, when they do, they’re framed as tactical decisions rather than strategic bets.
The absence of a true technology strategist at the leadership table leaves CEOs to navigate a high-velocity, high-stakes environment without a seasoned guide.
Why “Wait and See” Is the Wrong Strategy
For some leaders, the default approach is to wait and see. After all, every technology wave comes with hype—and not every tool will be relevant for your business.
But here’s the flaw in that thinking: AI and advanced digital capabilities aren’t single products or platforms. They’re enablers. The companies that are winning today are those that are experimenting early, learning fast, and building capabilities before they’re urgent.
“Wait and see” in 2025 means you’ll be evaluating options in 2027, implementing in 2028, and realizing impact in 2029—while your competitors are already reaping benefits and moving on to the next wave.
In other words: by the time it’s “safe” to adopt, the competitive advantage is gone.
The CEO’s Role: Appoint a Strategic Technology Mind
The solution is straightforward in principle but challenging in execution: ensure that someone with deep, strategic technology expertise is actively engaged in shaping your organization’s future.
This person may be:
- A full-time CIO or CTO with proven strategic chops
- Good ones are not cheap, but can make ALL the difference
- A seasoned virtual CIO or fractional CIO with experience in your industry
- A senior advisor aligned with your leadership team on a regular (we suggest weekly) basis
What matters is not the title – it’s the mandate. This person must have a seat at the table when growth strategies are discussed, acquisitions are considered, or new markets are explored. They must understand the technology landscape deeply enough to see how emerging tools can be leveraged for your unique business model.
And they must be empowered to connect the dots between tech opportunity and business outcome.
Thinking Beyond Efficiency: The Top-Line Opportunity
Many CEOs (and sadly, some IT leaders), subconsciously frame IT’s purpose as enabling efficiency – reducing costs, streamlining operations, automating repetitive tasks. That’s necessary, but it’s only half the story.
The real opportunity in today’s environment is to use IT and AI as growth engines.
- Data-Driven Revenue Models: Using analytics to identify profitable niches or personalize offerings at scale.
- AI-Enhanced Products: Embedding intelligence into your core offerings, making them more valuable to customers.
- Strategic Automation: Elevating the human intelligence in your organization out of repetitive tasks and onto activities with high ROI.
- Market Expansion: Leveraging digital channels and predictive modeling to enter geographies or verticals you could never serve before.
- Service Innovation: Reimagining the customer experience in ways that create loyalty and pricing power.
hese aren’t hypothetical. Midmarket players in manufacturing, financial services, healthcare, logistics, and many other industries are already deploying these strategies, and they’re winning market share from incumbents who underestimated them.
The Cost of a Blind Spot
The irony is that midsize companies are often more agile than Fortune 500 firms, but they squander that advantage when they lack strategic technology leadership.
Without it, they tend to:
- Over-invest in legacy systems while ignoring emerging platforms
- Miss timing windows for market-shifting innovations
- Make reactive, fragmented IT decisions instead of coordinated, strategic ones
- Treat AI as a side project rather than a core business capability
And because these mistakes are cumulative, by the time a CEO recognizes the pattern, the damage is often significant.
The Clarion Call to Action
If you’re a CEO, the question isn’t whether technology will change your industry; it’s whether you’ll be the one driving that change or reacting to it.
Ask yourself:
- Who is scanning the horizon for technologies that could fundamentally change our business?
- Who is mapping those possibilities to concrete efficiency- and revenue-driving strategies?
- Who is ensuring that our data, systems, and processes are ready to support tech-driven transformation?
If the answer to any of those questions is not super strong, you have a gap. And in 2025, that gap is more than an inconvenience – it’s a strategic vulnerability. Bringing in a strategic technology mind (whether full-time, part-time, or advisory) is no longer a luxury. It’s a safeguard against irrelevance and a catalyst for growth.
The companies that will dominate the next decade are making those moves now. The only question is: will yours be one of them?
