Why moving from controller to CFo is not natural

Let’s talk about something I see all the time in growing businesses.

You’ve got a solid controller. They keep the books clean, close the month, manage cash flow, and make sure everything ties out. They’re smart, loyal, and detail-oriented.

So naturally, as your business grows, you look to them for more.

You start asking strategic questions.
What do the next 12 months look like?
Where should we invest?
What’s the smartest way to scale?

You’re hoping they’ll give you CFO-level thinking—forward-looking, insightful, strategic finance. But you’re getting silence. Or a shrug. Or another backward-looking report.

And maybe you’re frustrated. Confused. Wondering if you need someone new in that seat.

Here’s the thing most founders don’t realize:

Controllers were never trained to think like CFOs.

Not because they’re not smart enough. Not because they don’t care. But because that was never the job.

A controller’s job is to look backward. To make sure the books are right. That everything is accurate, compliant, reconciled, and reported.

A CFO’s job is to look forward. To build forecasts, model out scenarios, guide the business, and help leadership make smarter decisions.

These are totally different skill sets.

In a big company, the gap between the two roles is clear—and there’s a built-in ladder to bridge it. Controllers in large organizations have mentors. They sit in on strategy meetings. They learn from seasoned CFOs. There’s a path, a structure, a system for professional growth.

But in a small or mid-sized business?

They’re flying solo.

No CFO to learn from. No peer group to swap ideas with. No framework to build strategic muscles. They’re on an island, expected to somehow just know how to do a completely different job.

And that’s where things break down.

So the real question isn’t, “Why isn’t my controller giving me forecasts and strategy?”
It’s, “Who’s helping them grow into that role?”

Because here’s the truth: Most of them want to step up. They want to think more strategically. They want to be a bigger asset to the business.

They just don’t know how.

And that’s where I come in.

I’ve sat in that seat. I’ve been the solo finance person, trying to figure it all out. I know how it feels to be expected to lead without the tools, training, or support.

And now, I’ve built a mentorship program specifically to close that gap.

It’s designed for controllers and finance managers in growing businesses who are ready to level up—but need a roadmap. It gives them the strategic toolkit, the coaching, the peer network, and the confidence to move from “head of accounting” to “trusted advisor.”

The best part?

You don’t need to swap out your team.
You just need to support them.

When you invest in their growth, you unlock a whole new level of value—without the disruption of bringing in someone new. You get someone who already knows your business, already understands your numbers, and is now equipped to think like a CFO.

So before you start rewriting job descriptions or scrolling through LinkedIn for your next finance hire, ask yourself this:

What if your controller could grow into the role you really need?
What if the right support made all the difference?

If you’re ready to explore that, let’s talk. Because your controller might be closer to CFO-level thinking than you think—they just need someone to show them how to get there.