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 often the difference nobody has designed for, 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 explicitly decided that. But the compensation plan makes it a reasonable choice, and replacing the team may not change it.

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.

Give each deal a row and fill in four columns: who wanted it, who else had to say yes, where it stopped, and how long that stage took. For won deals, use the stage that held things up longest. For open deals, record the time so far. Leave gaps where you don't know.

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

Read the approval column alongside the delays. Compare those with a few normal-sized deals. Ten rows will not establish a cause. They can show you what keeps happening and where to look next.

If the approval path barely changed, look harder at qualification, positioning and seller execution. Hiring may be part of the answer.

If three or four new functions suddenly appear on nearly every stalled deal, you may have changed the buying process without changing how your team sells. That does not settle the question of whether the reps are good enough.

Look at what the champion had to work with. Arguments for each stakeholder? A business case and relevant references? Answers for security and procurement? A clear account of what implementation would involve?

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. The worksheet can point to where the buying process changed and what needs investigating. It cannot prove a single root cause.

If the pattern holds up, “hire better reps” is unlikely to be the whole answer. Work out how the deal gets sold inside the customer: who needs convincing, what they need to believe, and what proof would help. Give security and procurement a named owner. Make implementation clear. Then check whether the sales incentives still make sense for a five-month deal.

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.