When your sales team depends on you

If you’re a founder doing £2–3M ARR and still closing a lot of the revenue yourself, this is usually the point where things start to feel slightly off.

You’re still involved in most of the important deals - you know which ones are real, which ones aren’t, and where things are likely to land.

But if you step out of a deal, it often slows down or stalls.

On paper, the pipeline might look strong but, in reality, a lot of it still depends on you being in the middle of it.

At that point, most teams have a sales function in place. There are AEs, sometimes SDRs, and activity is happening.

However, a meaningful part of the number still relies on the founder stepping in at the right moments to move things forward.

Where founders tend to go wrong

The instinct at this stage is usually to add more capacity.

Hire another AE.
Hire another SDR.
Build more pipeline.

It feels like the logical next step and it can give you a short-term lift, but it also tends to introduce more variation.

Different reps run deals in different ways, so qualification starts to drift. Your pipeline grows, but becomes harder to trust. As a result, what you've created is more activity, but less clarity on what’s actually going to convert. You end up spending more time trying to interpret what’s real, rather than less.

Why adding another AE often doesn’t fix it

The underlying issue usually isn’t that there aren’t enough people. It’s that the way deals are being won hasn’t been transferred yet. A lot of what makes deals convert still sits with the founder:

• how opportunities are qualified
• how conversations are steered
• when to push and when to hold back

Until that’s been properly translated into something the team can run with, adding more people doesn’t solve the problem. It just increases the number of deals that need that same intervention.

So when do you actually need a Head of Sales?

Usually, it’s when you start to notice that:

• deals move at very different speeds depending on who’s running them
• pipeline looks healthy, but outcomes are inconsistent
• forecasting feels more like judgement than something you fully trust
• and you’re still the one deals rely on to get over the line

At that point, it’s less about generating more pipeline and more about making the existing pipeline work properly.

What the role actually is at this stage

The job isn’t to come in and “sell more”.

It’s to take what’s already working, which is often founder-led, and turn it into something repeatable across the team.

That tends to look like:

• bringing consistency to how deals are qualified and progressed
• creating a clearer picture of what a good opportunity actually looks like
• tightening up how pipeline is managed and forecast
• coaching the team in a way that actually changes behaviour, not just activity

Over time, the goal is that deals don’t depend on you being involved in the same way.

Title is less important than fit

Most companies will call this a Head of Sales, but the title isn’t really the point.

At this stage, someone who has only operated inside a well-structured, well-resourced sales organisation often struggles.

The role is closer to building than scaling. It needs someone who can take something that works in parts and make it work consistently.

The question that usually matters more

Most founders ask:

“Do we need another salesperson?”

The more useful question tends to be:

“If I step out of the next few deals, what happens?”

If the answer is that things slow down or stall, then adding more activity around the edges is unlikely to fix it.

Final thought

If revenue still depends on you being involved, it’s rarely just a pipeline problem. It’s usually that what’s working hasn’t been transferred yet. Until that’s in place, another AE often just creates more of the same problem, not less.