Have you started sentences with "once we've got a VP Sales in" more than twice this quarter?
Is the founder still on every deal that matters?
And when somebody asks what the VP would actually do in their first ninety days, does the room go a bit quiet?
That last one is the useful question. Most businesses know roughly when they want a sales leader. Far fewer can say what the leader is meant to fix, and that gap is where most of these hires go wrong.
The Honest Test: Do you have a motion, or do you have a Founder?
There's a version of this hire that works, and it starts from something specific. You have two or three Reps carrying quota. At least two of them are hitting it. And you can explain, without hand-waving, why the deals that close, close.
That's a motion. A motion can be scaled, and scaling it is a real job for a real Leader.
The other version is the one where the Founder is the best salesperson in the business by a distance, nobody has written down why, and the plan is to hire someone who will "work it out". That person exists, but they're rare, they're expensive, and they are almost never the person on the shortlist you're about to look at. Far more often you hire a good scaler into a builder's job. They spend six months looking for the playbook that doesn't exist, then they leave, and everyone concludes the market is thin.
The market isn't thin. The brief was.
Builder or Scaler - pick one out loud
This is the single most useful conversation to have before you speak to a Candidate.
A Builder writes the playbook. They'll sell personally for a year, work out the ICP by getting it wrong a few times, and hire the first proper team off the back of what they've learnt. They tend to be comfortable with mess and less interested in a big org chart.
A Scaler takes something that already works and adds people, process and predictability to it. They're brilliant when there's a machine to tune. They're miserable when there isn't one, because their whole toolkit assumes a baseline that isn't there yet.
Very few people are genuinely strong at both. The ones who are usually don't want the job you're offering.
Say which one you need, out loud, in the first meeting with your board. If the Founder says Builder and the Board says Scaler, you've just saved yourself four months.
Don't skip the layer underneath
The pattern we see most often is an expensive one.
A Business goes from three reps to eight, decides it now needs Leadership, and hires a VP. The VP arrives and discovers they're running eight one-to-ones a week, doing all the deal coaching themselves, and rebuilding the forecast from scratch every Monday. They're not leading. They're first-line managing with a VP title.
Sometimes what you actually need is a strong Head of Sales or a first-line manager, and a Founder who stays close for another two quarters. That's a cheaper hire, it's a faster hire, and it buys you the time to build the motion properly before you ask someone senior to scale it.
We've told people this and lost the fee. We'd rather do that than place a VP into a job that was never going to work.
VP Sales or CRO? The Titles aren't interchangeable
A VP Sales owns the sales team and its number.
A CRO owns the revenue line - which usually means Sales, Customer Success, Revenue Operations, and often Marketing, all reporting in.
The titles get swapped around a lot, sometimes for fundraising optics, and that causes real problems in a search. Advertise a CRO role that's really a VP Sales scope and you attract people who'll be frustrated inside six months. Advertise a VP Sales title for genuine CRO scope and you lose the people who could have done it, because they read the title and assume the remit is smaller than it is.
Candidates ask about scope early. A vague answer reads as a warning sign to the good ones, not as flexibility.
Should you promote your best AE?
Sometimes. Just be clear about what you're rewarding.
Closing brilliantly and leading well are different skills. Building a forecast you'd bet on, coaching a rep through a bad quarter, saying no to a deal that would land this month and unravel next - none of that shows up in a personal quota attainment number.
Some of the best sales leaders we've placed were solid rather than spectacular reps who happened to be unusually good at making other people better. And some of the strongest closers we've met were quietly relieved when someone gave them permission to stay in the seat.
If you do promote internally, treat it as a genuine change of job. Give them the support that deserves.
What to write down before you start
Four things, on one page, agreed by whoever has a vote:
- The number, and what it's made of. New logo, expansion, or both.
- Builder or Scaler.
- Scope - does CS report in, does Marketing, does the Founder still own the top ten accounts.
- What they're allowed to change in the first six months. If the honest answer is "not much", you want a manager, not a leader.
That page is worth more to the search than any long list of candidates. It's also the thing that stops a board and a founder discovering they disagree at offer stage, which is the most expensive place to find out.
So - When?
When there's a motion to scale, a layer underneath to lead, and a written answer to what the job actually is.
Not when the deck says you should have one by now.
If you're somewhere between "we probably need a VP Sales" and "we're not sure what we need", that's a good time to talk.
We recruit VP Sales and CRO roles for B2B software companies across the UK, the US and Europe, and we'll happily tell you if the answer is not yet.
