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The CIO’s mandate: Transform legacy into enterprise agility

Ken Stillwell, Accedi per iscriverti al blog

Your competitors are investing millions to modernize. You’re spending even more just to keep legacy systems alive. And here’s the uncomfortable reality: Modernization may feel expensive, but the cost of not modernizing is far higher.

Every year you delay, you’re paying a premium for slow change, brittle integrations, operational risk, and a workforce that’s aging out of your most critical systems. Meanwhile, your competitors are reallocating legacy spend into AI-ready platforms that compound efficiency, speed, and customer satisfaction.

Modernization isn’t the financial burden.

Legacy is.

So the real question is no longer whether you can afford modernization.

It’s how much longer you can afford the status quo.

And this isn’t just anecdotal. In a recent study of 180 enterprise leaders, 75% said legacy systems are significantly impacting their organization’s performance – not in pockets, not occasionally, but across the enterprise. When three quarters of the leadership team is fighting their own infrastructure, you don’t have a technology problem. You have a strategic one.

Every CIO sees the warning signs: flat cycle times, slipping SLAs, and customer systems straining under outdated architecture. These aren’t technical annoyances –they’re symptoms of an enterprise being held back by legacy foundations. And when performance drags quarter after quarter, boards don’t blame the systems. They expect leadership to fix it.

Modernization has shifted.

This is no longer a technology project. It’s a leadership mandate.

Legacy isn’t “stable.” It’s a strategic liability.

Legacy systems don’t quietly sit in the background. They actively shape how your business operates:

  • They resist integration with cloud and AI. 
  • They scatter data across incompatible systems. 
  • They trap teams in manual workarounds. 
  • They drain budgets that should be funding innovation.

Large enterprises now waste $370M+ each year just maintaining legacy systems. That’s not investment – that’s leakage.

And the workforce risk is accelerating. The mainframe engineers, COBOL developers, and custom workflow specialists who know your systems best are retiring in waves. Salaries are soaring as the talent pool shrinks. Recovery times stretch because institutional knowledge is walking out the door.

Modernization isn’t just a technology decision.

It’s a resilience decision.

For CIOs, the cost of delay compounds like debt. Every quarter you extend the life of legacy systems, you increase future cost, future risk, and future constraints.

Why modernization keeps getting deferred

Every CIO has heard the same rationalizations:

“We don’t have the budget.” 

You’re already spending more than modernization would cost.

“It’s too risky right now.”

Standing still is the highest-risk strategy on the table.

“We need a full roadmap first.”

A perfect plan is the fastest path to zero progress.

“The business isn’t aligned.”

Every strategic priority – experience, efficiency, growth – is already limited by legacy foundations.

"Delay doesn’t create stability."

It creates fragility.

Modernization succeeds when outcomes lead and architecture follows

The CIOs who move fastest don’t lead with architecture diagrams. They lead with outcomes:

  • What has to improve in the next 90 days? 
  • Which workflows are blocking performance? 
  • What’s the smallest modernization move that unlocks measurable value?

This flips modernization from an unwieldy multiyear effort into a sequence of targeted wins the business can feel immediately.

When outcomes lead:

  • Alignment improves 
  • Skepticism decreases 
  • Funding gets easier 
  • Momentum builds 
  • Architecture becomes purposeful

This is the approach separating CIOs who modernize from those still planning to modernize.

Where successful CIOs start: Modernize the constraints first

You don’t need a three-year architecture reset. You need tangible movement in the next 6–12 weeks.

Nationwide didn’t start an enterprise redo. They tackled a specific bottleneck: dispute resolution. By modernizing the workflow itself, they moved cycle times from 15 days to two – a change the business immediately felt.

Truist followed the same approach. They defined the outcomes – straight through processing, fewer errors, faster resolution – and architected backward from those goals.

This is the modernization formula that works: Outcome → Microjourney → Architecture → Delivery. It’s fast, targeted, low risk, and builds enterprise confidence.

Modern platforms deliver fast wins and future scale

Big bang rewrites are dead. CIOs now prioritize platforms that:

  • Deliver value in weeks 
  • Plug into existing systems 
  • Reduce technical debt incrementally 
  • Prepare workflows and data for AI

In other words: CIOs choose momentum over monoliths.

The IT modernization flywheel

Modernization should accelerate – not stall – as you move:

  • Consolidate systems → free budget 
  • Automate workflows → free people 
  • Unify data → enable AI 
  • Deploy AI → move from reactive to predictive

Once the flywheel turns, it becomes self-funding. But someone has to start the push.

That someone is the CIO.

The cost of not acting

If modernization stalls:

  • Technical debt compounds 
  • Incident risk increases 
  • Costs rise 
  • Performance drags 
  • AI becomes nearly impossible to deploy

And the numbers back this up: 79% of leaders say legacy systems are blocking their ability to deliver new automation, and 71% say legacy is blocking AI innovation outright.

If your foundation is legacy, your AI strategy is already compromised.

Legacy doesn’t just block today’s improvements.

It blocks tomorrow’s capabilities.

No CIO ever says: “I’m glad we waited.”

Most say: “We should’ve moved sooner.”

The mandate: CIO-led, business-aligned modernization

This isn’t a technology refresh. It’s the architecture for:

  • AI strategy 
  • Operational efficiency 
  • Customer experience 
  • Enterprise speed 
  • Risk management 
  • Growth 

You can’t deliver modern outcomes on legacy infrastructure. You can’t deploy AI on systems built before AI existed. And you can’t delegate modernization and hope it resolves itself.

Nationwide didn’t wait.

Truist didn’t wait.

The CIOs driving these transformations chose to lead.

A Blueprint for CIOs ready to move

The CIOs who modernize fastest follow three principles:

  • Outcome-first Blueprint 
  • Center-out transformation 
  • Rapid test drives

This is how modern enterprises finally break free from legacy: with speed, confidence, and lower risk. It’s the modernization model every successful CIO is now adopting.

Ready to accelerate transformation with speed, clarity, and confidence? Check out the resources below:

  • Fireside Chat: The Real Cost of Legacy. Listen as Ken Stillwell discusses why legacy drains growth and how leaders can break free fast. 
  • Research Report: What 180 Leaders Say About Legacy. Explore the data behind legacy’s true cost and the modernization moves that work. 
  • Retire Tech Debt for Good: A practical, AI-accelerated path to replace legacy in one decisive step.

Tag

Argomento: Legacy Modernization

Informazioni sull'autore

Ken Stillwell serves as Chief Operating Officer and Chief Financial Officer at Pegasystems, where he leads global operations, financial strategy, and large‑scale transformation initiatives. A frequent voice on modernization, AI‑readiness, and enterprise resilience, Ken helps organizations break free from legacy constraints to accelerate sustainable growth. He is a champion of client success, operational excellence, and Pega’s values‑driven culture—guiding leaders to move with clarity, speed, and confidence in an era of continuous transformation.

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