You were good at selling.
Really good, actually. You smashed your number, got promoted, and someone decided you were ready for the big leagues.
So they gave you a bigger quota, told you to chase 6 and 7-figure ARR deals, and wished you luck.
And now you're drowning.
I know, because I was there. I think every single enterprise salesperson has been there.
And not because it's some noble rite-of-passage, but because training salespeople at that level is woefully bad.
Almost everywhere.
The Poison Chalice
Most companies treat the jump from SME to enterprise like a promotion. A reward. Bigger number, bigger opportunity.
What it actually is, is a completely different job. Well, maybe not totally. But it's a BIG difference!
SME sales is fast. You're mostly one-on-one. You pitch, you handle objections, you close. If you lose the deal, there's another one next week.
Just smile and dial, right?!
Enterprise sales is a different animal. Fifteen stakeholders, a game plan that shifts every fortnight, and if you make the wrong call you don't just lose a deal. You lose 12 months, probably end up on 0% of target, and end up looking for a new job.
But nobody tells you that when they hand you the new territory.
Why It Falls Apart
In SME sales, the person you're talking to is usually the person who decides. That's not a small detail. That's the whole game.
Once you're past 250k ARR, you're not selling to a person any more. You're selling to an organisation. And organisations are a hot mess!
Twelve stakeholders, all with their own agendas, and a procurement function that didn't exist in your last role.
There's a business case process nobody walked you through.
There's an RFP you need to manage - create strategy docs and orchestrate an entire bid team.
You're expected to navigate all of this with the same skills that got you through 50k deals.
Really?!?!
What Pisses me off
This isn't a talent problem, mostly. I meet salespeople all the time who are absolutely capable of selling at this level.
They're not failing because they can't. They're failing because no one ever taught them how.
It's not malicious neglect by companies.
The reality is most businesses don't understand sales in the first place, so trying to explain the difference between simple and complex sales is like asking a basic carpenter to create you an ornate carving - related trade, different skill level.
And the skills are not obvious.
How to read a buying committee. How to map political influence inside an account. How to build a business case with your prospect rather than just for them. How to spot when your so-called champion can't actually championing anything. When to go wide across the organisation and when to go deep with a single thread.
Trying to learn this by trial and error is brutal. You don't find out you made a mistake in week two. You find out in month nine, when the deal you've been forecasting all year quietly dies and you can't understand why.
What This Actually Costs
Most businesses don't even clock how expensive the gap is.
They see a missed target and blame pipeline. They see a slipped deal and put it down to timing. They see a heavy discount and assume the market is just competitive right now.
What they don't see is a salesperson who couldn't navigate the buying process. Who couldn't read the room well enough to know the deal was dying three months before it officially went cold.
Familiar?
If any of this feels familiar, whether you're the rep who's out of your depth or the leader watching your team grind through big deals they keep losing, stop pretending the problem is effort.
The skills it takes to sell a 50k deal are not the same skills it takes to sell a 500k deal. And seven-figure deals in regulated industries are another level again.
And if you've read this far, you know what I'm saying is true.
If you want to build those 7-figure skills, there's no magic button, but there are a network of skills you can learn.