A letter about your first sales hire

Hiring your first salesperson is the biggest bet you will make, and the odds are worse than you think.

Around seven in ten first VP Sales hires are gone inside twelve months, and fewer than half of account executives hit quota. If you're running on eighteen months of cash, and the median Series A now goes to companies at around $2.5m of ARR, then nine months spent on the wrong hire is half your runway gone and no closer to the bar. I've watched it happen enough times to want to write this down.

Before anything else, work out what this bet actually costs you.

I'd rather you saw your own number than one I made up. Put in what you've really budgeted and change anything that doesn't match your situation. Every default has a source under it, including the nine months: that's roughly how long average ramp runs without structured onboarding, according to the Sales Management Association, which is about how long it takes before a bad hire is undeniable.

The candidate is almost never the reason it failed.

Everyone blames the person anyway. The founder does it first, quietly, then blames themselves later. Look at what actually happens, again and again:

• They interview brilliantly, because interviews test how well someone sells themselves. They cannot test whether someone can sell your product without you in the room.
• The impressive one from the big company arrives and cannot hunt, because they have only ever sold with warm leads handed to them.
• The honest post-mortem, when it comes, sounds like David Roy, writing about his own first sales hire: "The first salesperson I hired lasted three months. Not because they couldn't sell... because I couldn't tell them what actually worked."
• And with nothing written down, the ramp eats a quarter of the year's revenue, and you get pulled back into selling anyway.

None of that is a talent problem. When the community that has watched this a thousand times rules on it, the verdict is always the same two words: hired too early. What they mean is that the process was still in your head. Nobody can be hired into your head.

So you go looking for help, and this is what the market offers you.

The book on your desk is good, and it hands the writing back to you, which is the one thing you haven't got time for. The recruiter sells you a person on a refund window that closes around day ninety, while the Bridge Group put average ramp at 6.2 months: the guarantee expires before the answer arrives. The fractional sells you a quarter of strategy, and the playbook turns up at the end, if it turns up at all. And the playbook your chatbot wrote reads beautifully right up to the moment a stranger has to sell from it.

The step everyone skips is getting what you know out of your head.

You instinctively do a few things which helped you open up your market. How you position your product, who you sell it to, how you introduce it, how you respond to objections, what a serious buyer looks like, what's a valuable trade for you: all these, and many more, live inside your head. Some survive the transition from you doing them to someone else, some don't.

This is the Sales Extraction Audit. I study how you've unlocked revenue and produce the artefacts that make it possible for a stranger to come into your company and succeed at selling.

You end up with five documents, and they're written in your language.

Each one has a job, and each has to pass its test before I call it finished: a researcher who's never met you should be able to build a hundred-name prospect list from your ICP document alone, and a stranger should be able to send your second email. On top of them you get the two things you actually decide with: a written hire-readiness verdict, and the eight-week ramp plan for the person you hire.

• The ICP specification. Who you sell to, in observable criteria a stranger could apply: title, company shape, trigger events. The test: they could build your prospect list without asking you anything
• The outreach playbook. How you reach them: sequences, scripts and cadence, written so someone who has never sent your second email could send it
• The discovery framework. The questions in order, what a qualifying answer sounds like, and the red flags that mean walk away
• The objection library. What buyers actually say, what each objection really means, and the answer that works
• The closing process. Proposal, presentation, negotiation boundaries, and the handoff into onboarding

Here's what changes for you and the person you hire.

For you: You interview against something. The question becomes whether they can run your discovery framework in a role-play without you rescuing them, rather than whether they seem impressive in a room. When you finalise a hire, you have a structure to ramp them and manage their performance. And if by week four they can't get meetings, you can look objectively at where they need help. This is the gate we call Activate: interest becoming real conviction, and today it only clears when you're the one in the room.

For them: Their first week is reading rather than shadowing, so by day two they can build a prospect list without booking time with you. They know what a good conversation sounds like before they have their first one, and when a buyer pushes back they reach for your answer instead of improvising their own. They can tell whether they're on track without having to ask you. And when they do need you, it's for the judgement only you have, not for the thing nobody ever wrote down.

And who am I to be telling you this?

I've spent the last thirteen years selling enterprise software, and the four before that building a company of my own to 80 staff. I have done the zero-to-one multiple times, across industries, continents and solution types. I have carried the number, established partnerships, hired, fired and run teams… This audit is me sharing the lessons I learnt the hard way in the field. The full history, numbers and all, is on my LinkedIn.

There are three ways to do this, depending on how far in you want me.

Handover ends on purpose. By month three you have the content, the tools, and a quarter of supervised practice: the difference between a technical founder and a manager of salespeople. If it needs to run longer, we're having a different conversation about a different engagement.

If you're about to make your first sales hire, or you made one and it didn't work, we should talk.

The Sales Extraction Audit may be the hedge that protects your next hire and your runway. Fifteen minutes, no deck, no pitch. You tell me where the deals actually come from, and I'll tell you honestly whether this is the right thing for you right now, and which of the three versions fits. If it isn't right, I'll say so and point you at what is.