Everyone I talk to wants the same two things. They want to win, and they want to make money.

It comes out as one sentence. It's two.

Most of the time they run together and you never have to think about it. Good product, good year, good check.

But they can come apart. And when they do, the money is the part you notice, because you get a number for it every month. Nobody sends you a number for whether you're winning.

So the question isn't whether you're making money. It's whether you get anything out of what you're building besides the check.

A few weeks ago I talked to a seller six and a half years into the only job he's had since school. Founding SDR, then team lead, then AE, now the senior rep on the SMB team. He was there when it was about 20 people and a couple million in ARR. It's roughly 200 people and $50M now.

That's a win. Genuinely. Most companies don't do that, and he was there for the whole thing.

He carries 400K and closes about 500K. He's at 140 percent this year. Average deal, 20 to 25K. He told me his floor to move is 275.

He also told me, without my asking, that he doesn't touch renewals or upsells. He closes new business, hands it off, checks in on the account because he likes to, and that's where it ends. Three-year deals, none of the expansion. His words for his own position were low hanging fruit.

And there's a move on the table, SMB up to mid-market, that he's passing on. Too many mouths to feed up there, the way he put it. He runs the math and lands on more responsibility for less money next year.

Each of those decisions makes sense on its own. Add them up and here's where he stands. The company went from $2M to $50M, he's had a great year, and what he has to show for six and a half years is a stack of 25K deals.

The check clears every month. The other thing you find out about later, when you go looking and see what your record lets you do next.

And there's a way to check where you stand on that, which is your deal size. Not your percentage. Your deal size.

Work backwards from a 250K OTE, which usually sits on something like a million-dollar quota. At a 25K average deal, that's 40 closes a year. At 50K, 20. At 100K, ten. At 250K, four.

When founders describe the seat to me, deal size is usually in the first two sentences. We need someone who's sold six-figure deals into this buyer. I don't get many briefs built around 40 closes a year at 25K.

So a rep closing 500K in 25K chunks has a great year behind him and 25K deals on his resume. Both true. The percentage says he's excellent at the job he has. The deal size is what a founder reads to decide if he can do theirs.

Percentage is a rate. Deal size is a ceiling.

Plenty of reps who close 25K deals could close 150K deals. That's not the problem.

The problem is nobody's going to let you find out on their dime. A founder filling their first sales seat, with runway running out, isn't going to be the place you try it for the first time. They'll hire someone who's already done it.

Which leaves one place you can do it. Where you already are.

The time to ask is while you're over quota. Ask for the enterprise accounts nobody's covering. Ask to work the biggest open opportunity alongside the founder. Ask for the logo everyone wants and nobody has touched. And ask what happens to your accounts after signature, and whether any of it can come back to you.

You don't need ten of them. One or two closed at three times your average changes what a founder sees when they read your record.

The move he's turning down is the deal size move. That's the thing worth arguing about, not next year's W-2.

I place people. My whole week points toward telling you to go get the bigger seat.

Sometimes the money now is just right. Mortgage, kids, a number you need this year. Take the money. Just know that's what you're doing.

And bigger isn't automatically better. Two deals slip and the year is gone.

When a founder gives me the profile and deal size is in it, I look at reps with spotless records, five straight years over quota, real skill, and I don't put them forward. Not because they couldn't do it. Because I can't make the case with what's on the page, and I'm not going to spend a founder's shortlist proving a point.

So I'd rather tell you now, while you're at 140 percent and can still do something about it, than have you hear it from someone like me in two years.

You can get paid very well by a company that's winning and get almost nothing else out of it.

The check tells you about this year.

The size of what you close tells them what you can carry somewhere else.

So go ask for the bigger deal now, while you're the rep they don't want to lose.

This is the kind of thing we get into on the Founding AE call. Second Friday of every month, no cost, no pitch. Reps talking about the stuff you can't take to your manager, like whether the promotion that pays less is worth taking.