The mistake isn't hiring the wrong person. It's hiring the right person for the company you used to be.

I spent 14 years at one company.

Same company. Same logo. Same mission.

I watched it go from Series A through years of growth and ultimately through a PE acquisition.

But the people we needed at year 2 were almost unrecognizable from the people we needed at year 12.

I didn't understand that at first.

Early on, we needed people who could operate without a map.

There weren't many processes. There wasn't much specialization. Half the time, we didn't even know what the job would look like six months later.

So we hired builders.

Generalists. Scrappy operators. People who could walk into a mess and figure it out.

That was exactly right for that stage.

Then the company changed.

Revenue grew. Teams got bigger. Customers got more sophisticated. The cost of mistakes went up.

And I made a mistake of my own:

I kept hiring for the company we had been, not the company we were becoming.

The profile that had worked brilliantly at $5M didn't necessarily work at $50M.

What had once looked like resourcefulness could become lack of process.

What had once looked like speed could become inconsistency.

What had once looked like being a generalist could become a lack of depth.

The company hadn't just gotten bigger.

The job had changed.

That's the part nobody talks about.

VC-stage hiring and PE-stage hiring can have the exact same job title and require completely different people.

At the earlier stage, you're often hiring for:

Range. Speed. Ambiguity. Building.

At the later stage, you're increasingly hiring for:

Depth. Scale. Repeatability. Accountability.

Neither profile is better.

They're better for different moments.

And PE creates another inflection point.

A company can have a perfectly capable leadership team and still need a different one for its next value-creation plan.

The CEO who built the company to $100M may not be the person who can take it to $300M.

The VP of Sales who built the first sales organization may not be the person who can build an enterprise GTM machine.

The Head of Product who successfully launched the platform may not be the person who can lead the company through an AI transformation.

That doesn't mean the people are bad.

It means the company changed.

AI is making this happen even faster.

This is what I'm seeing now across PE-backed software companies.

AI isn't simply creating new technology.

It's changing:

• What companies build

• How teams operate

• Which capabilities matter

• Where leverage comes from

• And ultimately, which leaders are required

And I'm seeing an interesting gap emerge.

Companies that grew up alongside AI are often building around it from the beginning. Companies that have spent years building successful organizations are having to adapt leadership teams that were designed for a different operating model.

That's a fundamentally different challenge.

We recently spent 18+ months embedded with a PE-backed software company going through an AI transformation.

We ultimately recruited 25+ people, including 15+ Director/VP-level leaders across Product, Engineering, AI, Revenue and Operations.

We didn't start with a plan to make 15 leadership hires.

The organization kept changing.

A new capability created a new constraint.

The constraint required a new leader.

That leader changed what became possible.

Then the organization evolved again.

That's how I think about hiring now.

Not:

"Who's the best person for this job?"

But:

"What is this company becoming, and what kind of leader does that version of the company require?"

That's a fundamentally different question.

And it's the biggest lesson I took from 14 years inside one company:

The biggest hiring mistake isn't hiring a bad leader.

It's hiring a great leader for the company you used to be.