Questions we answer Hiring and headcount

Should I hire another salesperson?

Only once you know whether the constraint is demand, conversion or capacity. Another salesperson adds capacity; it does not on its own create a pipeline or fix a way of selling that is not working.

Start from this question

Free · a few minutes · starts from “I think we need another person”

The short answer

Add a salesperson when the pipeline is genuinely larger than the current team can work, when the sales process is understood well enough for someone new to follow it, and when you know what a new person would own. Do not add one to fix a conversion problem, an unclear proposition or a process that only works when the founder runs it — a second person will reproduce the same result twice, and the cost of finding that out is a year of salary.

Sales headcount is easy to justify and easy to get wrong. A second or third salesperson multiplies whatever the first one is already doing — which is good news if the way you sell works, and expensive news if it does not.

The useful test is what is actually scarce. If the people selling have more qualified conversations than they can hold, capacity is the constraint. If they have time on their hands and nothing worth spending it on, the constraint sits upstream of them.

Is it really this?

Worth checking before you spend anything. These are the signals that tend to tell the two apart.

Signs it is

Qualified leads are going unworked, or being picked up too late to matter.
The people selling are meeting their numbers and the constraint is hours in the day.
There is a way of selling that can be taught, and somebody with the time to teach it.
The founder is doing the selling and it is crowding out work only they can do.

Signs it's something else

The salespeople you have are not hitting target, and a second person is more likely to repeat that than to fix it.
Most of the day goes on proposals, CRM updates, scheduling and chasing rather than talking to buyers.
Leads are plentiful but poorly qualified, so the time goes into conversations that were never going to close.
Nobody can describe how a deal is actually won, so there is nothing to hand over.

What's usually behind it

A revenue target that arrived without a plan for how it would be met.
One salesperson at capacity, where nobody has separated the selling from the admin around it.
A thin pipeline, where more activity feels like the obvious answer.
Founder-led selling that has worked so far and is now taking the founder's whole week.

What people usually get wrong

Recruiting a salesperson to create demand when the gap is marketing, and then judging them on it.
Expecting a new hire to build the sales process and work it at the same time, against a quarterly number.
Handing a new salesperson the leads nobody else wanted, and reading the result as a verdict on them.
Setting the ramp expectation from the founder's own numbers, which were earned with authority and relationships the new person does not have.

The options, and when each one fits

In no particular order. Which of these fits depends on your situation, not on the question you typed.

Recruit another salesperson
Qualified demand is going unworked, the sellers you have are at capacity, and the way you sell can be taught.
Take the admin off the sellers you have
They sell well but spend much of the week on proposals, scheduling and keeping records straight.
Fix the pipeline before adding to the team
There is capacity to sell and not enough qualified conversations to fill it.
Bring in a specialist for a stretch
You need the sales process designed, or a new market tested, before committing to a permanent seat.
Develop someone already in the business
Someone in account management or delivery already holds the relationships and wants the role.

When doing nothing is the right call

If the pipeline is thin and nobody can yet say why, a quarter spent finding out is cheaper than a hire made on a guess. Set the date now, decide what you will measure — qualified conversations, not activity — and look again then.

What the diagnostic asks

What a new person would mainly add: capacity, a missing skill, or both.
How long the need has been there and whether it is growing.
Who owns the work today, and how much of how you sell is written down.
Whether a permanent hire is realistically fundable, and how soon this needs sorting.

“I don't know” is always an answer. Nothing is assumed on your behalf.

The routes it weighs

Every diagnostic weighs all ten routes. These are the ones that tend to matter for this question — a description of the rules, not a promise about your answer.

Recruit
Recruit a new person for a durable, sizeable need that is central to the team.
Process improvement
Change how the work flows — remove steps, name an owner, fix the hand-offs.
Develop
Build the capability in someone already in the team, with time and support.
Specialist support
Bring in a freelancer, consultant or specialist for a defined piece of work.
AI Assist
Keep a person in charge and give them AI for drafting, summarising, checking or analysis.
Do nothing yet
Record the issue, set a revisit date, and decide what would change your mind.

What changes the answer

A repeatable, documented way of selling makes a hire far more likely to work; an undocumented one points at writing it down first.
Qualified demand that is already going unworked strengthens the case for capacity.
A target that depends on new demand rather than more conversations points somewhere other than sales headcount.

Get your own read

A handful of short questions, then the strongest route for your situation, what's also credible, what we still don't know and what would change our view. No account, no setup.