"I have a concern about this VP of Sales hire. Not because he isn't talented. Just... not the right timing," I said.

She didn't love hearing that.

The candidate she'd found was genuinely exceptional. VP-level background. Came out of a company that had just sold for over a billion dollars. Well-respected in the industry. The kind of baller hire where you send the offer letter and your whole team pops bottles. Finally. Now we can grow.

I understood the instinct completely. Revenue had stalled. The sales team wasn't converting at the rate she needed. She'd done the work to find someone real... and she had. He was real.

The problem wasn't the hire. The problem was what he was going to walk into.

This was a high-ticket coaching program making a little under $10M a year.

Good company. Solid product. A team that genuinely cared.

But underneath the surface... disorder.

Not chaos, let me be clear. The company was running… okay. But "running okay" and "ready to scale" are two different places, and the founder was about to pay $450K a year to find out the difference.

The coaches were the sales team. Great at coaching, okay at closing. They were taking inbound calls — a couple dozen a week — and doing their best. No dedicated sales function, no SDRs, no CRM that anyone actually trusted. Revenue operations was essentially a spreadsheet and a prayer.

The founder had diagnosed this as a leadership problem. She would need someone to come in and own sales, build a team, develop training.

She wasn't wrong. She would need that person.

Just not yet.

She needed the leader. But she hadn't yet built the thing for the leader to lead.

Most founders don't have a Growth Operator embedded in their company who can say, "Yo. Sorry. Bad idea to hire right now."

That's why the data looks like this:

If your fulfillment process failed 40% of the time and cost 5x to fix, you'd shut the whole thing down. Executive hires get a shrug and a LinkedIn post about "a learning experience."

Because the failure is quiet. There's no moment where everyone agrees why it went wrong. It just slowly becomes "not the right fit."

Why do these roles fail so often? It depends.

But I can grab my crystal ball and tell you how the first 6 months would have played out if this VP of Sales was hired into this environment that wasn't ready for him:

Weeks 1-6: He's excited. New role, new challenge. He sits down with the team, asks to see the pipeline. Someone pulls up the CRM. Records are incomplete. Half the leads don't have source data. There are automations nobody's touched in eight months. He asks what the close rate is. Three people give him three different numbers.

Six weeks in, he still doesn't fully understand what he's working with. The "sales team" he was hired to lead are coaches who take inbound calls when they're not coaching. Good people. Not closers. He's spending most of his days doing RevOps work... cleaning records, mapping lead flow, building a single source of truth.

This is not what he signed up for. He doesn't say that out loud.

Month 3: The infrastructure is cleaner. He's got a better picture of what's working now. But the call volume hasn't changed — still a couple dozen a week. You can't build a sales team on that. You can't train closers who don't have calls to close. You can't move revenue with a top-of-funnel that marketing hasn't scaled yet.

He starts raising the marketing dependency in leadership meetings. Things get a little tense.

Month 6: Revenue hasn't moved meaningfully. The founder is frustrated. The hire is frustrated. The board (if there is one) is asking questions. Everyone's looking at each other wondering what went wrong.

And here's the thing — nothing went wrong. He walked into a system that was never ready for him. The conditions that make a VP of Sales effective simply didn't exist when he arrived. He didn't fail. He just inherited an environment destined to.

This is why the sequencing matters as much as the person.

It's like hiring a world-class boxer before you've built them a ring.

Early in my career, I was at an exec company where the founder had expensive taste.

Private jets to speaking gigs. A beautiful new office. A culture of big moves and bold bets. From the outside, it looked like a company on its way somewhere.

From the inside, I was writing marketing copy because we “couldn't afford” a $3,000/month copywriter. I'd look at the P&L, then look at the flight receipts, then back at the P&L, and genuinely wonder if I was losing my mind.

But that wasn't even the part that stuck with me.

What stuck was watching them hire. Every six months, a new senior person would come in. Always someone real — experienced, credentialed, exactly the profile you'd want. And every time, the same sequence. They'd spend the first few months trying to orient. Start raising concerns. Things would get tense. Then they'd leave, or get pushed out.

And the story would become: we just haven't found the right people yet.

I was in the room. The people were fine.

The environment wasn't.

It's never fun to be the wet blanket on a decision a founder is excited about. So before I recommended holding off on this VP of Sales hire, I asked myself:

Could this person actually move the primary needle in their first 90 days?

For a VP of Sales, that comes down to one thing above everything else: is there enough qualified call volume that a closer can close? Everything else — the CRM cleanup, the attribution work, the RevOps foundation — can be built around the edges. But if marketing isn't producing enough pipeline to build a sales team on, no amount of leadership changes that. You're asking someone to drive a car that doesn't have an engine yet.

At this company, the honest answer was no. So the hire would have spent its first 90 days creating the conditions it needed to succeed... instead of doing the succeeding.

The founder sees a revenue problem. The sales team sees a sales problem. Nobody in that room is positioned to ask whether the environment is actually ready for the solution. That's usually how I end up in the room.

Most $3M-$10M companies have a version of this in their future.

Revenue stalls. The instinct is to hire. The hire gets made. The system doesn't support them. They can't produce. Everyone's confused. Another expensive exit. The founder decides they have a talent problem.

You don't have a talent problem.

You have a conditions problem.

If you're thinking about making a senior hire right now... ask yourself the question I asked before recommending she hold off:

Could this person actually move the primary needle in their first 90 days? And if not... what has to be true before they can?

If you can't answer that specifically, you're not ready for the hire. You're ready for the work that comes before it.

—Chris Piper
The Growth Operator