Hiring your first salesperson too early

The most expensive hire a founder makes is usually the first salesperson, and not because of the salary. It is expensive because when it fails, it takes a year to find out, it costs the founder confidence, and it usually produces the wrong conclusion: that salespeople do not work here.

Almost every time I see it go wrong, the same thing happened. The founder hired someone to solve a problem the founder had not solved yet.

The one question that decides it

Can you describe, in specific terms, a sale that has worked more than once?

Not "we've sold to fifteen customers." Fifteen customers who each bought for a different reason, through a different route, at a different price is fifteen one-offs. It looks like traction and it does not transfer.

What transfers is a pattern: this type of buyer, with this trigger, tends to move through roughly these steps, in roughly this time, at roughly this price, and here is what they object to on the way.

A first salesperson scales a sale that works. They cannot invent one.

Signals you are ready

• You can name the trigger. You know what is happening in a buyer's business in the weeks before they start looking.
• You have lost deals for reasons you understand. Predictable losses mean you can see the shape of the thing. Random losses mean you cannot.
• Your pricing survives contact. You are not renegotiating the model on every deal.
• You are turning work away or dropping balls. There is more demand than you can personally serve.
• You can say what the first 90 days look like for a new seller, in detail, without making it up on the spot.

Signals you are outsourcing a problem

• "We need someone to get us leads." If you do not know who to sell to, a salesperson will not find out faster than you. They will guess, and their guesses are worse than yours.
• Every deal you have won came from your own network. That is a relationship business, not a repeatable one, and a new hire has none of your relationships.
• You are hoping the hire will tell you what the product should be. That is a founder job wearing a sales badge.
• You cannot say what they should be paid for. If you cannot define the target, you will end up measuring activity, which measures nothing.

What "good" looks like at this stage, and it is not who you think

Founders reach for the impressive CV: someone senior, from a bigger company, with a big-name logo behind them. That person often struggles, because their skill is running a machine that already exists. You have no machine.

At the first hire you want:

• Comfortable with ambiguity. They will have to write things down that do not exist yet.
• Genuinely curious about the customer's world. Technical enough to hold a conversation with your buyer without you.
• Prepared to do the unglamorous half. Prospecting, CRM hygiene, follow-up. There is nobody else to do it.
• Able to take coaching from someone who is not a salesperson. That is you, and it is a real requirement.

Hire for the stage you are at, not the stage you want to be at.

Set them up so you can tell what happened

Give them three things before day one, or you will not be able to read the result:

• A written target. Who to go after and, just as usefully, who to leave alone.
• Your qualification rules and your decision rights. What they can decide without asking.
• A 90-day expectation that is not revenue. If your sales cycle is four months, judging them on closed revenue at 90 days tells you nothing. Judge the leading things: qualified conversations with the right profile, second meetings, deals reaching an agreed process.

The cheaper experiment first

If you read the signals above and you are honestly in the middle, do not hire yet. Spend a month selling deliberately instead of instinctively - same target, same pitch, written down, tracked - and see whether a pattern appears. It usually does, and it usually costs you nothing but attention.

Then hire, and hire into the pattern.

So before you write the job ad: could you hand someone one page tomorrow that tells them who to call, what to say, and what a good deal looks like?