The signature moves upstairs

Before hiring enterprise reps, look at who had to say yes

The company decides to move upmarket. Deals worth 5k become deals worth 60k.

Six months later the pipeline is full and nothing closes. The explanation is ready before anyone asks for it. Our reps can't sell at that level. Too transactional. No presence in a steering committee. We need people who have done enterprise.

Any of it can be true. I have seen each of those be true.

But all of them describe the seller, and none of them describe the deal. They rest on one premise, and nobody tests it: that this is the same sale, only bigger.

That premise is worth one morning before the job ads go out.

A bigger deal is not the same deal

At your usual price, the person with the problem signs. They hold the budget, they decide, and the conversation is one conversation.

Above a certain number — it is different in every company, and every company knows its own — that person can no longer sign. They become a champion: someone who now has to sell your product internally, to people who do not have the problem. Finance, who reads a cost. Security, who reads a risk. Legal, who reads an exposure. Sometimes an IT team, who reads work. Sometimes a committee that meets once a month.

Your deck was written for the person with the problem. Nobody has written the one for the four people who decide now, and your champion carries it alone into a meeting you are not in.

That is the whole difference, and it appears nowhere in the CRM. What appears in the CRM is: stalled.

There is a second mechanism, quieter. A thirty-day cycle becomes a five-month cycle. A rep paid on the quarter does the arithmetic and goes back to selling the small thing. Nobody decided that. The compensation plan decided it, and it will keep deciding it after you have replaced the team.

I learned this from the comfortable side

At SAP I closed large deals and thought I was good at it.

There was a bid desk. A legal team who had seen those redlines a hundred times. Someone who answered the security questionnaire in two days. A reference programme. An internal business case, already written, for the finance director on the other side of the table.

I saw none of it. I saw myself closing.

It took a much smaller company for me to find out how much of what I had credited to myself was infrastructure other people had built. The first time a deal sat for weeks inside a security review that nobody owned, I understood what SAP had been doing for me.

That is not modesty for effect. It is the reason that when a company tells me its reps cannot sell enterprise, I look at the approval path before I look at the reps.

You can check this in a morning

Take the last ten deals meaningfully above your average — won, lost, or still open.

For each one, write down two things: who wanted it, and who else had to say yes. Names or functions, whatever you have. Then where it stopped, and how long it took.

Do not interpret yet. Put the ten side by side.

Now read the third column top to bottom, and compare it with what that column looks like on a normal-sized deal.

If it holds the same one or two people, your sellers are the variable, and hiring is a reasonable answer.

If it holds three or four functions you have never met, and the same one appears on almost every row, you are not looking at a selling problem. You are looking at a deal that requires an internal case your company has never written, handed to a champion holding a deck built for somebody else.

Hiring an enterprise rep solves the first. It does not write the case.

On your last ten large deals, who else had to say yes — and what did you give your champion to convince them?

What I can’t do : I can't tell you from a table whether a rep can sell enterprise. Nobody can. What I can see is where the approval path changed, which function keeps appearing on the rows that stall, and what your champion was given — or never given — to get past them.

Isn't this an excuse for reps who can't sell big?

No. The table cannot tell you whether someone can sell. It tells you whether the approval path changed and whether anyone equipped the team for it. A weak seller and an unequipped deal produce the same forecast, and they need opposite responses.

We already hired an enterprise rep and it still doesn't close.

Then the table is worth more, not less. An experienced enterprise seller usually knows exactly where the deal stops. Ask them for the ten rows rather than the CRM — it will be faster and more honest.

How is this different from a sales audit?

An audit produces a document and a proposal. This produces ten rows you fill in yourself, and either a repeating pattern or no pattern at all. If there is nothing in it, there is nothing, and I will say so.