Founders hire a head of sales because they want a line in the sand. They want someone to own the numbers, drive revenue growth, build the sales strategy, run the sales team, and give them a plan.

Sometimes, that’s what happens. But usually it doesn’t. If your sales process isn’t repeatable and understandable yet, you’re not hiring a head of sales to help you scale. You’re simply recruiting someone to be buried in the same chaos that’s currently burying you. Sure, you’ll free some of your time up for other things, but you’ll still be the CEO of a company with a broken sales function.

Stage-appropriate sales leadership

The reason behind this confusion (one I’ve seen many smart, savvy CEOs fall foul of) is that they think a sales leader will create the sales approach from scratch. But that’s actually YOUR job, as the founder. A sales director or head of sales should be focused on doing one job really well. Scaling a sales process that is already teachable and repeatable. They’ll need to help refine and improve those things as the function grows, but they need a solid starting point.

A good sales director candidate will have a proven track record inside a working machine. They can manage sales managers, set sales targets, build dashboards, run forecasting revenue meetings, execute sales strategies, and keep the sales departments marching in the same direction, working towards the same goals.

That’s exactly what you need. The only problem is getting the timing right. Hand that person a broken sales process and ask them to scale it and all you’re doing is making a problem bigger (and harder to unpick).

If you’re still finding product market fit, still refining the pitch, still learning which customers convert, still patching holes in the sales process week to week, then the job is still yours.

The two-rep rule

The best advice I have for hiring a head of sales is often ‘don’t do it’. At least not yet. Wait until you have at least two sales reps consistently hitting their targets.

And I mean consistently, not a lucky quarter where a huge contract dropped into your lap. Not forecasting that two good months in a row will mean we’ll be billionaires by this time next year, Rodney. Two sales reps, hitting their numbers, quarter after quarter, against clear sales targets.

Once you’ve got that, you’ve got proof the sales strategy works. And you’ll always need to own that in the first instance. Once you’ve proved your message is landing with the right parts of the market, once people are responding to it, once you have a sales process that is teachable, then. And only then. Do you have something a sales leader can start to build from.

I know it sounds slow. It sounds like I’m advocating being overly cautious, holding back your potential, limiting your ambition. I’m not. It’s about avoiding hiring the wrong type of sales leader, or hiring them too early, and setting yourself back months or even years as a result.

What if I already have two sales reps but they are not hitting target?

Then you do not need a head of sales. You need to fix the basics.

Is the sales strategy clear? Is the market right? Are you chasing the right customers? Is there a repeatable sales process? Is the sales funnel leaking at the top, or are leads not converting? Is the offer priced correctly? Do your reps have a strong understanding of what you’re offering?

If you’re not sure, that’s the answer. Hiring a head of sales to solve uncertainty is expensive. Build clarity first. Then hire.

The stretch sales director

When you are ready to hire a head of sales, resist the temptation to go after the fully formed sales director archetype with the perfect CV.

Instead, look for what I call the stretch director. Someone in a senior commercial role with a growth mindset who is hungry to prove themselves in a bigger role.

This is someone who is still senior sales talent but is one step below the title you are hiring for. They want the senior role. They have leadership skills, but they still have the scrappiness to do the work. They have enough experience to be credible, but not so much baggage that they will try to import a playbook from their last company.

The seasoned executive director type often comes with a rigid sales methodology. They’ll try to copy and paste it. When it doesn’t work in your market, with your customers, with your pricing, they blame the product or the team. That’s how you end up with expensive churn inside the sales departments.

The stretch sales director is more likely to build with you, not above you. And most importantly, they’re more likely to accept the reality of the role: hands on, close to customers.

The best sales professionals at this stage are often the ones still close to the work. That’s why someone motivated by career growth is often the right sales leader for a scale-up.

The travel test

Here is a simple test I use in interviews for head of sales.

Ask: “What will you do in your first two weeks?”

If the answer is “strategy”, “process”, “territory planning”, or “CRM audit”, then don’t touch them with a bargepole.

You want the sales leader who says: “I’m going to spend my first two weeks with customers.”

Not talking to the rest of the team about the customers, wading through data on existing customers, or intimately reading up on your ICP. Someone who wants to get out there, sit down with the people you currently serve, and ask them what’s working for them (and not working) and how the relationship could improve.

In the early stages, those customer interactions are worth more than any internal process. Your head of sales needs to understand key customer relationships, and what actually works in your market.

That is also how you build the company’s sales success over time. A head of sales who hides in spreadsheets will build an incredible dashboard that just hides the fact that they don’t really understand the customer.

Customer visits first. Process second.

The bag-carrying requirement

Your first head of sales must carry a quota. Full stop. No debate, no negotiation.

A head of sales who refuses to carry a bag is telling you something important. They see the job as managing sales managers and reporting sales data, not as doing the selling.

In a scale-up, that is a problem.

You need to be running a player-coach model, and it is the only model that works at this stage. Your head of sales needs to be in deals, closing alongside sales reps, demonstrating the behaviours they expect from the team.

If your head of sales is not willing to pick up the phone, run a demo, and close a deal, they will not coach effectively. They will track sales metrics and manage activity, but they won’t understand why deals actually close, or have the product knowledge to move deals forward.

The contact book myth

Do not hire a head of sales because they “know all the CIOs” or have “key accounts in financial services” or whatever version of the address book pitch they give you.

Those relationships were built in a different context, selling a different product, at a different company. They rarely convert.

The CIO who took their call when they were at a household name is not automatically taking their call when they are at your company, selling a product they have never heard of.

This myth is persistent because it feels like certainty. It feels like they’ll bring you a bigger market share simply by walking through the door on their first day, without you having to earn it.

It doesn’t work like that.

You need someone good at building your pipeline by identifying opportunities. Hire the head of sales for their ability to build new customer relationships, not for their address book. Hire for business development skills, not who they say they play golf with.

The energy test

Sales is emotional.

You can pretend it is just process and forecasting revenue, but the reality is that the work is rejection and recovery, all day. That’s why sales leadership matters.

Your head of sales sets the tone of the team.

Be careful about hiring a head of sales who prefers a quiet, polite, “library” atmosphere. They might be brilliant strategists. But sales floors need energy. Noise. Collaborative tension.

You want a head of sales who brings momentum. Someone who builds strong relationships, makes sales reps want to pick up the phone, and celebrates the first meeting booked with the same enthusiasm as the closed deal.

In the early days, culture is created by the head of sales. You cannot fake it.

The right sales leader is a people hire, not just a numbers hire. Yes, they need analytical skills and to understand sales data. But they also need interpersonal skills to help them coach and lead.

The 48-hour rule

Fast, confident decision-making is one of the biggest tells in a head of sales hire. If they can’t make a call on a candidate within 48 hours of an interview, they don’t have the pace you need in a scale-up.

This job is judgement under imperfect information. You’re never going to have the full picture. If they’re waiting for certainty, they may as well not make a decision at all.

And it’s not just hiring. It shows up everywhere: qualifying deals, calling time on dead opportunities, making pricing calls, choosing where to focus, and fixing territory messes. In a fast-paced environment, a sales leader who deliberates endlessly slows down your entire sales function.

Look inside first

Before you spend £30,000 on a recruiter, look at the people already on your team.

Half the time, the best future head of sales is already sitting in your sales team. They’re not the loudest. They’re the one who naturally helps the other reps, tightens the talk track, shares what’s working, and quietly improves the process without being asked.

If you’ve got a renaissance rep who’s already doing that, promoting them into a team lead role is often a safer bet than hiring an external “big gun” who doesn’t know your product, your customers, or your culture.

The killer advantage of an internal move is simple: you already know they can sell your thing, in your market, to your customers. That’s the hardest part to validate in any external hire, no matter how shiny the CV looks. And what’s more, if you’re not offering internal development opportunities, you’ll lose your best people to competitors who are.

Fire fast (again)

The same rule that applies to reps applies doubly to leaders. You’ll know within 30 days whether this is going to work.

Are they in front of customers? Are they coaching reps on real deals? Are they carrying a bag and proving the motion still works when they run it? Or are they building org charts, asking for headcount, and booking “strategy sessions” that produce a deck and no pipeline?

The cost of keeping the wrong head of sales for six months isn’t just their compensation package. It’s the sales team’s morale. It’s the pipeline you didn’t build. It’s the trust you burn with your best reps who watched mediocrity get tolerated at the top.

So hire your stretch sales director. Put them in front of customers on day one. Give them a bag to carry. And if the leading indicators aren’t there within a month, make the call.

After all, what’s worse. Firing someone after 30 days, or explaining to your board in 12 months why the sales function has gone backwards?

How to run the head of sales search without wasting six months

If you are going to hire a head of sales, treat the search like a proper project. Don’t wing it or outsource the thinking to an executive search firm. Use executive search for reach, not judgement.

Here is the search approach I like.

Write the sales leader scorecard first

Before you start the executive search, define what the right sales leader looks like for your stage.

Do it in plain English.

  • Must have carried a quota recently.
  • Must have built a sales function, not just managed one.
  • Must have coached sales reps on real deals.
  • Must have a strong track record in a similar market.
  • Must be willing to travel and meet customers.
  • Must have a proven ability to read market trends and adapt their approach.
  • Must be able to build and develop strategies with imperfect information.

That is the job. That is what you are searching for.

Then, and only then, run the search for the best candidates.

Use work tests

If you want to assess sales leadership, watch them do it.

Give them a real scenario.

Ask them to review your pipeline and explain what they would do next, or to pick three deals and show how they would coach the rep.

Find out how they would use sales data and performance metrics to improve sales performance.

If they can’t get specific, they are not the right head of sales.

Make them demonstrate they can build customer relationships

Do not just ask them about customer relationships. Make them show you.

Give them a shortlist of key accounts in your market, then ask them to draft an outreach plan and talk about how they would open new business conversations without relying on brand.

This is where the contact book myth dies. The right head of sales will build from scratch. The wrong head of sales will talk about who they know.

The founder’s role does not go away

Even with the best head of sales in the world, you are still selling.

You are still the founder. You are still the person customers want to talk to when the deal is big. You are still the person who can move pricing, product, and delivery decisions quickly. You are still the person who carries belief.

Your head of sales makes selling less dependent on you. But you still need to work closely with them on big deals, pricing decisions, and anything that needs founder-level conviction. They do not remove you from the picture altogether.

Your challenge

Before you hire a head of sales,be clear on what, exactly, you are asking them to scale.

If you can’t describe your sales process, you need clarity before you can scale.And if you can describe it, stop hoping a big title will save you. Go and hire someone who’ll carry a bag, spend time with customers, and make a direct impact on your business. Because the fastest way to waste a year is hiring a head of sales to turn chaos into dashboards.

Book a free discovery call with Dominic.

Written by business coach and leadership coaching expert Dominic Monkhouse. You can order your free copy of his new book, Mind Your F**king Business here.