By Jeffrey Shear, J Shear Consulting

One of the most common questions I hear from CEOs of growing companies is some version of: "Do we need a CIO?"

It usually comes up at a turning point. A major system decision is on the table, technology spending is climbing faster than revenue, or the board has started asking questions nobody can answer confidently. The instinct is to hire someone.

Having been a CIO for much of my career, my honest answer is often this: you need the judgment, not necessarily the headcount. Those are two different problems with two different solutions.

What "CIO-level judgment" actually means

A good IT manager or managed service provider keeps the lights on: devices work, systems are patched, tickets get closed. That's essential, but it's execution. CIO-level judgment is something else. It's the ability to:

• Sequence and say no. Decide which of the 15 initiatives on the list matter now, which come later, and which should never happen.
• Negotiate from strength. Know what a fair software contract looks like, where vendors have flexibility, and which terms will hurt you in year three.
• Translate technology into business outcomes. Explain to a CEO or board what a decision costs, what it returns, and what the risks are — without jargon.
• Manage risk. Keep cybersecurity, business continuity, data privacy, and now AI governance proportionate to the business.
• Design for where you're going. Make choices today that won't need to be ripped out when you double in size.

Signs you're missing it

You don't need a formal assessment to know whether this gap exists. Look for these patterns:

• Your IT support is responsive, but no one owns a technology roadmap.
• Software subscriptions have multiplied, and nobody is sure what's being used.
• A major decision is coming: an ERP or CRM replacement, an AI initiative, an acquisition, or a new line of business.
• Technology projects routinely run over budget or quietly stall.
• The board or investors ask about cybersecurity or AI, and the answer is "we're looking into it."
• The CEO or CFO is making technology decisions by default, and knows it.

Your three real options

When a full-time CIO is the right answer

Fractional leadership isn't always the answer, and I'd be doing you a disservice to pretend otherwise. A full-time CIO usually makes sense when:

• Technology is core to your product or customer experience, not just a support function.
• You have a sizable internal technology team that needs daily leadership.
• You operate in a heavily regulated environment with continuous compliance demands.
• You're in a multi-year transformation where strategic decisions come weekly, not quarterly.

If most of those describe you, hire the CIO. Fractional support can still help you define the role, recruit well, and bridge the gap until they start.

When fractional leadership fits

For many companies between roughly 30 and 300 employees, the strategic workload is real but not constant. You might need intense involvement during a system selection, then a few days a month to keep the roadmap, budget, and vendors on track. Paying a full-time executive salary for that pattern rarely makes sense. Getting no senior guidance at all is how expensive mistakes get made.

Fractional leadership gives you the experience of someone who has seen the movie before, sized to the work you actually have.

A composite example

Picture an 85-person professional services firm, a composite of engagements I've seen. They were days away from signing a multi-year ERP contract. The vendor proposal was polished, the internal champion was enthusiastic, and nobody on the leadership team had been through an implementation before.

With fractional support — about one day a week — they paused, pressure-tested the requirements, and discovered they were buying modules they wouldn't use for years. They renegotiated to a phased rollout, reduced the first-year contract value by roughly a quarter, and built an implementation plan the team could realistically absorb. Then the advisory engagement scaled back to a monthly roadmap review.

They didn't need a CIO. They needed someone who had sat on the other side of that negotiating table many times.

What enterprise experience brings to a growing company

In large enterprises, good technology judgment is built into the structure: architecture review boards, vendor management offices, formal risk committees. Growing companies can't afford that bureaucracy, and shouldn't want it. But they can benefit from the same thinking, delivered by one experienced person in a fraction of the time.

Getting the most from fractional leadership

• Define outcomes, not hours. A roadmap, a vendor decision, or a board-ready technology plan.
• Give them a seat at the leadership table. Judgment is only useful if it's heard before decisions are made.
• Pair it with execution. Your IT team or MSP does the work; the advisor sets direction and holds the standard.
• Review regularly. Scale the engagement up or down as needs change, including deciding when it's time to hire full-time.

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If you're weighing whether you need a CIO, a fractional advisor, or just a second opinion on a major technology decision, I'm happy to talk it through.