The commercial technologist gap

JR
Jake Rose Technology Executive Search Partner
June 2026
5 min read

There are a lot of brilliant technologists who can’t draw a line between what they’ve built and what it’s worth in terms of value to a business. And a lot of businesses who’ve never had someone in the technology seat who could show them what that function is capable of producing commercially. This common disconnect is where I’ve seen most technology leadership hires go pear shaped!

This is the problem we founded Innova to solve.

The gap

On one side, you’ve got technologists who are talented and often have the highest IQ in the business. They build impressive platforms, lead strong teams, build enviable cultures engineers want to be a part of and modernise complex estates. They’re not bad at what they do. Ask them what it delivered for the business, though, and you usually get architecture decisions, not commercial outcomes. They’ll tell you about the migration, not about the margin it protected. They’ll talk about the team they built, not about what that team produced in terms the board could measure.

I’m not saying technical depth doesn’t matter. It’s the baseline. But the leaders who plateau are the ones who never fully grasp that commercial outcomes come first at this level. They can’t bring the SLT on the journey with them. They can’t translate what they’re building into terms a CFO or a PE operating partner understands (or cares about!). That limits how far they go, and it limits what the business gets out of them.

The businesses are the mirror image. They have treated technology as a cost centre for so long they don’t know what a commercially grounded technology leader looks like. They have never had one. The brief describes the technical function because that’s all they’ve seen the role do. They hire for what they know, get the same result, and assume that’s what technology leadership is. It’s a self-fulfilling prophecy.

I’ve watched both sides misread each other for years. That is partially what makes it so satisfying when it goes right.

Effort is becoming a commodity

What’s different now is that effort and process are becoming a commodity. A lot of what justified technology headcount and budgets over the last decade, the sheer volume of work, the complexity of managing it, the process around delivery, is being compressed by tools that didn’t exist two years ago. The organisations that understand this are already asking harder questions about what their technology function is actually producing.

In that world, you can’t hide behind good process or time and materials or the amount of work done. The value a technology leader creates has to be obvious. Not buried in a roadmap or justified by activity. Connected to something the business can point at.

This isn’t a future problem. It’s happening now, and the technology leaders who haven’t made the transition from technical operator to commercial operator will find the market less forgiving than it was.

Where idealism becomes a risk

Purpose and commercial grounding are not mutually exclusive. Some of the strongest technology leaders I’ve placed care deeply about the quality of what they build and can also tell you exactly what it delivered commercially. That combination is what makes someone senior.

What I am saying is that idealism without commercial grounding is a risk at this level. If someone’s definition of success is a well-built platform rather than a business that’s worth more because of what they delivered, they’re the wrong hire for most of the businesses we work with. It doesn’t make them a bad operator. It makes them a bad fit for a situation where outcomes have a dollar number attached to them.

The culture question

I push back on one assumption a lot. Commercial intensity does not mean toxic culture. PE-backed businesses, fast-growth environments, places where people work hard and move fast, these get a bad reputation. And some of it is earned to be fair. But the best versions of these environments are places where people are energised by the pace, where there’s a shared outcome everyone’s pulling toward, often equity-based, and where the scrappiness is the point, not a symptom of dysfunction.

That’s the sort of place I’d want to be in. Not a slow-moving enterprise with layers of bureaucracy where nothing gets decided. The people who thrive in the environments we work in are people who get out of bed because the work matters and there’s a clear end goal. When it’s done right, everyone’s pulling in the same direction. That’s not toxic. That’s alignment, and it’s great to be a part of.

What we test for

Saying you place commercial operators is easy. Building a process that finds out whether someone is one is the harder part, and it’s where most searches miss.

The way I assess technology leaders throughout a search is built around this gap. I’m probing for the link between what someone built and what it delivered. I’m looking for battle scars, the evidence that they’ve operated under pressure, made hard calls with resources they didn’t have, and come out the other side with outcomes they can point to. Good theory doesn’t cut the mustard. I need the specific moments where it was difficult and they made it work anyway.

The candidates who come through that process well are the ones who have already made the transition from technologist to commercial operator. They don’t need to be taught to think commercially. They’ve been doing it, and the evidence is in how they talk about their work, not just in their CV.

Frequently asked questions

It’s the gap I run into on most of my searches. On one side, technology leaders who build good work but can’t tell you what any of it was worth to the business. On the other, companies that have treated technology as a cost for so long they wouldn’t recognise a commercial technology leader if one sat in front of them. The market keeps putting those two together, and that’s where the hire goes wrong.
No, and I push back on that whenever it comes up. The best technology leaders I place care a lot about what they build and can still tell you what it returned. The problem is only ever having one side of it. Deep technical skill with no commercial instinct gives you impressive work that doesn’t move the business. Commercial talk with no technical credibility, and the team stops trusting you. You need both, and people who have both are rarer than you’d think.
I ask them what they built and what it did for the business, then I listen to which language they reach for. The ones who’ve made the shift go straight to the outcome, the margin, the revenue, the hard call they made under pressure. The ones who haven’t stay in the technology, the team, the process. Both are fair things to talk about, but only one tells me they’ll think commercially when it counts.
JR
Jake Rose
Co-Founder & Technology Executive Search Partner, Innova Search
Jake partners with investors, boards and CEOs on critical technology leadership hires across private equity, ASX-listed and high-growth businesses.

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