If I Were Selling Enterprise Software to a CIO Today

If I were selling enterprise software to a CIO or digital leader today, I wouldn’t start with the company history, or the feature-function-upgrade pitch. I’d start with the mess.

Because that’s where they are at. Buried under years of one-off decisions that looked rational at the time.

Every department, every function, every well-meaning executive made a choice. And those choices now compete, conflict, and rarely connect.

So I’d talk about the real thing that’s broken: the enterprise no longer works as a system. It is a broken down body. It works as a set of silos loosely joined by overworked integration teams and apologetic slide decks.

Everyone senses it. The CIO knows this. But software vendors rarely say it out loud. That’s inauthentic.

Instead, the conversation (pitch) is padded with empty buzzwords we’ve taught young sales people to say. Modularity, scalability, configurability. It’s all just shorthand for, “Don’t change a thing, just do the same stuff with our badge on it.”

Buyer autonomy isn’t the problem. “Better with us” isn’t even the problem. Alignment is. And that’s the lightbulb moment I’d push for.

CIO’s are held accountable for an environment they don’t fully own. They don’t pick all the tools. They don’t run all the projects. They don’t control all the budgets. But they’re expected to make it all work. So let’s talk about that.

As I wrote about last week, I don’t think the CIO lost control. I think they were told to hand it over. And they did. System by system, project by project, often under pressure to "empower the business."

The business wants flow, but bought silos. The board wants transformation, but funded tools. The result is that most CIOs don’t choose software anymore. They manage tension. Between speed and control. Flexibility and coherence. Departmental ownership and enterprise design. IT as a function is still expected to make it all work.

The CIO is left staring at a games cupboard full of mismatched puzzle pieces. None from the same set, and none that fit. So I’d ask the only question that matters: how much fragmentation are you willing to live with?

Don’t ask the CIO to undo what the business sees as empowerment. Autonomy has its place. But it is not the same as alignment.

So if I were in that room today, I wouldn’t pretend we were discussing or even debating a tech choice. This is a structural conversation about reclaiming enterprise design. Not to recentralise power, but to reintroduce coherence.

5 Questions

If you are ready to face the real challenge and not just sell another tool, these are the questions worth asking:

1. Who is shaping the logic of how your enterprise actually runs?
   Start by questioning authorship and control. This opens the door to a conversation about design, not tools.

2. What if the real challenge isn’t what’s missing, but what’s misaligned?
   Now you pivot from ownership to coherence. This frames the problem as structural, not functional.

3. What if the problem isn’t that you need more ERP software, but that nothing you already have works together?
   Then you bring it to the ground level, connecting strategy with what’s actually happening in their stack.

4. What if it’s not about adding new ERP, but finding a better way to make what you already have work together?
   This is where you start to offer a pathway forward. Less about procurement, more about orchestration.

5. And is your architecture absorbing complexity, or just amplifying it?
   Finally, you bring it home with a diagnostic question. It challenges them to assess whether their current path is solving or worsening the problem.

Then I would shut up and listen. Because this isn’t about talking over the CIO. It’s about creating space. It is arriving at the place where the real conversation begins. Not about platforms, not about procurement. But about the possibility that someone finally sees it clearly. That the challenge isn’t replacing systems. It is rethinking the logic of how the business runs, and giving the CIO the room to lead that redesign.

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CIOs do not lack vision. But somewhere along the way, we collectively walked away from some of the fundamentals of IT management. Specifically, the discipline of designing and governing the flow of information across the enterprise.

What we once called enterprise architecture has splintered into a thousand local optimisations. Technology is everywhere, but flow is nowhere. Integration is someone else’s job.

The pitch we need is not cloud-first. Not composable. Not future-ready. It is coherence. A shared architecture that restores flow and reconnects intent with execution.

As the conversation deepens, often over several meetings, the weight of legacy starts to press in. Inevitably, someone asks the question: Isn’t this just a battle between ERP and PaaS?

It’s not. That’s a false fight. It’s a comfort zone. As Lee Bolman and Terrence Deal famously stated, “When we don’t know what to do, we do more of what we know”.

The shift most software vendors don’t want to talk about is that ERP can no longer carry the enterprise on its own. It was built for structure, not experience. PaaS was built for movement, not control. One governs the data. The other governs the flow.

It’s symbiotic. ERP vendors need PaaS vendors. Together, they create coherence without regression. And it’s happening whether they admit it or not.

Companies like SAP and Oracle and Workday and Infor and many many more know they can’t win the enterprise alone anymore. That’s smart on their part. They’ve seen what happens when CIOs are forced to stitch everything together without a shared foundation. The result is not transformation. It’s not even entropy. It’s worse. It’s a cancer that ultimately ends in excision.

The sales pitch punchline is that PaaS is the quiet architectural force reshaping the enterprise. It doesn’t compete with ERP. It complements it. It doesn’t rip and replace. It wraps, connects, and orchestrates. It builds enterprise muscle without forcing a rebuild. While others chase composable dreams, PaaS platforms like Servicenow and Salesforce are becoming the connective tissue. Not just between systems, but across workflows, identity, data, and decisions.

But even that’s only part of the story. And one that software salespeople often get wrong. You can’t build a future by disowning the past. You need a vision for what’s next, yes, but you also need a legacy to stand on.

That’s why the “better with us” pitch falls flat. It’s not bold. It’s not new. It’s a tired trope. And it needs to be retired permanently from the toolkit.

The systems that got you here, the ERPs, the custom databases, the long-standing processes, all carry the institutional memory of the enterprise. You don’t just walk away from them. You surround them with better logic. You elevate them. You make them interoperable. You make them matter again.

The smartest CIOs aren’t burning it all down. They’re building forward, with context. Because the future isn’t greenfield. It’s layered.

And the platforms that win will be the ones that understand both sides of the equation: what must evolve and what must endure.

If you're not having that conversation, you don’t actually understand the real-world constraints and dualities CIOs face and you're not in their line of sight.

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If I were selling today, that’s what I’d offer. Not a product. Not a module. I’d sell a way to bring order back to the enterprise. I don’t think that’s old fashioned. I think it’s a way to restore design without sacrificing autonomy.

Because if the CIO has to keep managing chaos, they should at least have a platform that sees the seams of the business, not as flaws to be patched, but as the very places where real value lives.

That kind of thinking isn’t rooted in ERP anymore. It’s being shaped and accelerated by PaaS. Because coherence begins with honesty.

So what’s your opening line? Here’s mine:

“Before we talk about software, can we talk about the mess? Because that’s where every CIO I meet is starting from.”