Turning Technology into a Tailwind
IT Leadership for CEOs, CFOs and COOs
In many leadership meetings, technology shows up wearing a slightly uncomfortable label.
It’s often discussed as a cost to be controlled, a risk to be managed, or a set of issues that need resolving before the business can move on to more important things.
That’s understandable. We hear it regularly.
But in organisations that scale well, technology plays a very different role. It doesn’t dominate the conversation - it supports it.
In our experience, the difference isn’t about tools. It’s leadership.
When technology starts to feel more like obstacle than it should
Most mid-market organisations haven’t made “bad” technology decisions. What they’ve done is grow; quickly, pragmatically, and often under pressure.
New systems are introduced to solve immediate problems. Processes adapt around platforms. Responsibility for decisions is shared between finance, operations, suppliers and internal teams.
All sensible. All familiar.
Over time though, we often see the same pattern emerge:
Technology works, but feels more complex than it should
Decisions take longer because trade-offs are hard to assess
Costs are managed, but ROI is difficult to articulate
Senior leaders spend more time involved in technical detail than they’d like
At this point, technology isn’t broken. It’s just no longer pulling in the same direction as the business.
From headwind to tailwind
A headwind absorbs energy. It forces you to compensate. Progress is possible, but it takes more effort than it should.
A tailwind does the opposite. It creates momentum.
When technology acts as a tailwind, it:
Supports growth rather than constraining it
Reduces friction instead of adding complexity
Makes outcomes more predictable
Helps leadership teams move with confidence
We’ve seen this happen many times. And it rarely comes from a single system change or transformation programme.
It comes from clarity.
The leadership shift that changes everything
The most effective leadership teams we work with make a subtle shift in how they approach technology.
They stop asking, “What systems do we need?”
And start asking, “What outcomes are we trying to achieve?”
That change in framing has a powerful effect.
Technology stops being something to manage and starts becoming something to direct.
For CEOs, it brings focus.
For CFOs, it brings predictability and control.
For COOs, it brings stability at scale.
But - and this is the important part - it only works when someone is clearly accountable for making that alignment happen.
What good technology leadership looks like in practice
Turning technology into a tailwind doesn’t require constant innovation or sweeping change. In our experience, it comes down to a small number of disciplines applied consistently:
Clear ownership of technology direction and outcomes
A roadmap that reflects business priorities, not just technical ones
Investment decisions made with commercial context
Risks identified early, not when they surface
Regular review of what is genuinely adding value
When these disciplines are in place, something interesting happens. Board discussions move from issues to progress. Decisions get easier.
Why this matters differently to each leadership role
Although technology leadership sits at C-suite level, its value shows up differently across the team.
For CEOs, it removes noise. Technology stops competing for attention and starts supporting execution.
For CFOs, it brings clarity. Spend becomes intentional. Trade-offs are understood. ROI is easier to see and defend.
For COOs, it enables scale. Processes hold together under pressure. Growth doesn’t introduce fragility.
When technology is aligned properly, it supports all three perspectives - rather than pulling them in different directions.
Accessing the right level of IT leadership
Not every organisation needs the same answer.
Some businesses will justify a full-time CTO, CIO or CISO. Others will rely on strong operational teams and trusted suppliers.
Many sit somewhere in between.
What we’ve learned from working with mid-market organisations is that proportionate leadership matters more than structure. The right experience, at the right level, for the stage of the business.
That leadership can be internal or embedded. Full-time or fractional. Permanent or transitional.
What matters is that someone owns the direction - and is accountable for outcomes.
A useful sense-check
If you’re unsure whether technology is acting as a tailwind or a headwind, a few simple questions often surface the answer:
Are technology decisions helping us move faster - or slowing us down?
Do we have confidence in where we’re investing and why?
Is risk understood and managed early?
Do leadership discussions focus on progress rather than problems?
When leadership teams approach technology with clarity and accountability, it moves from something that absorbs energy into something that creates momentum.
And that’s when it becomes a tailwind.
Book an impartial strategy call
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No pitch. No obligation. Just perspective.