Could someone else close your next deal? Not someone brilliant, not someone who has sold for twenty years. Just a good seller, given what you have already got.
If the honest answer is "not yet", the plan to hire five sellers next quarter may be a few steps ahead of where the company actually is.
Founder-led sales is the right way to start. The founder knows the product, the buyer and the awkward questions, and every call teaches the company something. The hard part is knowing when to hand it over, and what you need to have in place first.
Let's Dive In!
The test is not revenue, it is repeatability
A founder who has closed a lot of deals has proved that the product sells. What they have not necessarily proved is that anyone else can sell it.
The clearest sign that you are ready is that you can describe the sale. Who the buyer is, what problem gets them to take a meeting, what the three or four stages look like, what usually kills a deal and how you answer it. Not in a slide, in plain words a new seller could act on.
If you cannot do that yet, the answer is not to hire faster. It is to spend a few weeks writing down what you already do.
Five questions to ask before the first hire
Ask yourself these, and try to answer with examples rather than feelings.
Has anyone other than the founder closed a deal, even a small one? A CS lead, a solutions person or an early employee who ran a deal end to end is worth a lot of evidence.
Do your best customers look alike? If they do, a new seller has somewhere to aim. If every customer is a one-off, they will spend a year finding out.
Can you say why you win, and why you lose? Not "our product is better", but the specific reasons you have heard from buyers.
Is there enough pipeline to keep another person busy? A new AE with no leads is an expensive way to find out that the founder was generating all of them.
Are you ready to let someone else run a deal differently from how you would? This is the one founders skip. If you will step in the moment a call goes off script, the new hire will never learn to run it.
Three or four honest yeses and you are probably ready. Mostly "not really" means the next job is the process, not the hire.
Who to hire first
A common instinct is to hire a VP of Sales, on the theory that a leader will build the machine. It can work, but it is usually the wrong first move. A leader with no team and no defined process spends their first months building both, while the founder waits and the number stays where it was.
More often, the first hire is one or two experienced Account Executives who have sold in a similar environment and can run a process once it exists. They do not need to be famous. They do need to have done the early version of the job and be comfortable without much structure.
A leader tends to make sense a little later, when there are a few sellers who need managing and the founder wants to step away from the day-to-day.
What to write down before they start
Before the first seller arrives, put together a short pack. It does not need to be polished.
The ideal customer and the three questions that tell you whether a prospect is one. The stages of a deal and what has to be true to move between them. The objections you hear most and how you answer them. Two or three recorded calls that show what good looks like, including one that went badly.
That is the material a new seller uses in their first fortnight. Without it, they invent their own version, and you end up with a process that changes with every hire.
The mistakes we see most often
Hiring for the sales team the company hopes to have in two years rather than the one it has today.
Hiring someone from a large, well-known company and expecting them to build their own pipeline, their own materials and their own process at the same time.
Handing over the deals the founder finds hardest and reading the slow start as a performance problem.
Stepping back completely on day one. A better pattern is to stay close for the first few deals, then move from running the call to reviewing it.
Measuring the new seller against the founder's numbers. The founder was selling to friends of friends with the product half-built in their head. The second seller is doing something different, and the target should say so.
So, is it time?
If you can describe how a deal is won, point to a customer profile you trust and see enough pipeline for another person, then yes, it is probably time to start. Begin with a scorecard for the first role: what the person needs to achieve in twelve months, and what they need to be like to do it.
If you are somewhere between "not yet" and "definitely", book a call and we will go through it with you.
