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Building a sales team: when and how to hire your first salesperson?

As a founder you do all the selling yourself, and that works until your calendar is full. A first salesperson seems the logical step. Yet that first hire often goes wrong, because everything that works is still in the founder's head. A salesperson who leaves after six months costs you half a year's salary, the time you put into onboarding and the deals that were left untouched in the meantime.

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Are you ready for your first salesperson?

Go through this list honestly.

You can say in one sentence which type of company your product works best for.You have customers who signed without it being a favour.You know how a sales conversation that leads to a deal goes.You know the average deal value and how long it takes to sign.Enough new conversations come in to keep a salesperson busy.You have time to guide that person during the first three months.

The mistakes we see most often

Hiring someone from a big company

A salesperson who worked for years at a well-known brand had a marketing team, a strong brand and a fixed process behind them. In a small IT or software company that person has to do everything themselves. That's a different kind of work, and it doesn't suit everyone.

No playbook

Without an explanation of who the ideal customer is, how a good conversation goes and what you do after each conversation, the new salesperson has to figure everything out themselves. That takes months.

Too few leads, too many expectations

A new salesperson who has to find their first customers themselves in a market they don't know will struggle. Hand over some of the ongoing conversations in the first months.

No goals for the first 90 days

If you're only judged on revenue, you don't know in the first months whether you're on the right track. Work with interim goals: first conversations in month one, proposals in month two, first deals in month three.

1First conversations
2Proposals
3First deals

What your first salesperson needs from day one

A one-page ideal customer profile: industry, size, who decides and what problem they have.
The structure of a good conversation, with the questions you ask yourself and the objections you often hear.
Your pricing logic, and who can give which discount.
A fixed follow-up rhythm after the first conversation and after a proposal.
Goals per month for the first three months.

That's essentially a playbook. It doesn't have to be a thick document. A few pages that are right are enough.

How we help

Step 1

Sales Analysis

In the Sales Analysis we put on paper together how you sell today, and look at whether you're ready to hire someone.

Step 2

90-Day Sales Sprint

In the 90-Day Sales Sprint we build the playbook, help with the profile and the selection, and guide the new salesperson's first months.

Ready for your first salesperson? Take the free sales scan

10questions

3minutes

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Your score straight away
Your 3 biggest levers, with cost and a first step
If you like, a free 45-minute call

Free and with no obligation. Your answers stay with us.

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Frequently asked questions

Should I hire a junior or a senior salesperson?

That depends on how much is already on paper. Without a playbook and ideal customer profile, even a senior will struggle. With a clear approach, a motivated junior can become productive quickly.

Should my first salesperson work entirely on commission?

Preferably not. In the first months there are still few deals, and a salesperson without a fixed income often leaves before they can become productive. A fixed part with a variable part on clear targets works better.

Is a freelance salesperson a good alternative?

It can be, for a fixed period and with clear targets. A freelancer needs a playbook too, otherwise you're paying for someone who has to figure everything out themselves.