There’s a new kind of executive search I keep seeing that inevitably sits open for months.
The title varies — Chief Transformation Officer, Chief Digital Officer, Chief Enterprise Officer. The pattern is the same…a growing company, often founder-led, decides it needs an executive to come in and own “Future of Work Strategy” which includes modernizing the technology backbone (e.g., AI) and redesigning how the company actually works. The search opens. It gets reposted. A year later, it’s still open (or worse, it’s been filled and it’s not going well).
The usual explanation is that the market for that person is tight. My read is different. The search isn’t failing to find the person. The spec is describing two very different people for two entirely unique seats.
Two jobs wearing one title
Read one of these descriptions closely and you’ll find both halves sitting right there in the bullets. The first half is platform ownership: selecting, implementing, integrating and governing the systems the company runs on — finance, procurement, HR, data. Demanding, specialized, permanent work. It never ends, because the stack never stops needing an owner.
The second half is operating-model redesign: changing how hundreds or thousands of people actually do their jobs, across sites, against habit. That is not systems work. It’s authority work. And it requires someone who can tell a peer their function has to change, and make it stick.
Both are real. They call for different people, different backgrounds, and — this is the part that gets missed (and it’s a pricey mistake) — different durations.
Permanent work, temporary work
Platform ownership is permanent. Hire for it permanently. In most companies that’s a VP or a senior director, not a C-suite seat.
Redesign is not permanent. Transformation comes in waves. To grow in a sustainable way, companies must develop the capability to transform repeatedly, but they cannot do so indefinitely without pause. Transformation has an arc.
I’ve held newly created executive seats of this kind more than once, and watched several more from close range. The pattern holds with uncomfortable regularity. The early years are the productive ones — the mandate is fresh, the sponsorship is real, the resistance hasn’t organized yet. Then the redesign lands. And once it lands, the work changes character: from making the new model happen to keeping it running. That second thing is a good job. It is not typically an executive job.
That isn’t a failure. That’s the shape of the work. Transformation mandates concentrate their value in the early years, and then, if they’ve worked, they convert themselves into an operating routine. At the tail end of a successful transformation is an existing team that can seamlessly keep the new normal running without the transformation leader who put it in place. So “success” looks like a transformation seat becoming unnecessary (at least until the next big transformation event, which could be months — even years — away).
This means a company hiring permanently for that half of the “empty executive seat” is making a permanent (and disruptive) decision about temporary work — and usually learning it the expensive way, well after the offer letter.
The objection, which is a good one
Here’s the strongest argument against everything I just said, and it deserves a real answer rather than a wave.
If you split the role, you’ve handed the hard half to someone with an end date. Executive teams are very good at waiting people out. A leader whose mandate expires in thirty months has less leverage than one who will still be in the room in year five, and the functional heads know it. Continuity is leverage.
There’s also the honest observation that transformation doesn’t actually end. There’s always a next wave. AI is the current one, and it will not be the last.
Both points are true. Neither one settles it.
The answer to the first is structural, not personal. A time-bound mandate needs explicit sponsorship, decision rights written down, and a CEO who says out loud that this person speaks with their authority. Companies that skip that step are the same ones where a permanent title has to substitute for real backing — and the title doesn’t work either. If the authority isn’t real, tenure won’t rescue it.
The answer to the second is that “transformation never ends” is an argument for building a capability (which, in my opinion, truly needs to become a core competency for long-term survival today), not for holding a seat. If every wave requires a new C-level hire, you haven’t built anything durable — you’ve built a dependency. The goal is an organization that can absorb the next change without needing a rescuer.
The question I’d ask
If a search like this is sitting on your desk, one question sorts most of it:
In year three (four, five), what does this person do all day?
If you can answer that crisply, and the answer justifies executive compensation, hire the seat. You’re right and I’m wrong for your situation.
If the honest answer is “by then it should be running itself,” you’ve learned something useful — before you spend another “X months” looking for someone who doesn’t exist or invested in an executive seat with a realistic two-to-three year lifespan.
Whole Enterprise™ works with executives and their teams to design for repeatable transformation; to build transformation as a core competency, not an individual function. If one of these searches is open on your desk right now, I’d genuinely like to hear how you’re thinking about it.