Hiring salespeople: a five-stage process for scale-up founders

85% of salespeople are serial underachievers. Not occasionally. Consistently. If you hired from the available pool at random, you’d be wrong four times out of five. Yet the average scale-up founder puts more thought into their pitch deck than their sales hiring process. Then they wonder why the team can’t sell. I’ve scaled two companies past £30m and spent years working with founder-CEOs on this exact problem. The same mistakes come up every time. Hiring too fast. Interviewing too few people. Deciding on likability rather than capability. The process below eliminates all three. This guide is for founders who already have a sales function and want to build it out systematically. If you’re making your very first sales hire, start with this post instead. The considerations are different and the process should be too. Here is the exact process I use. It’s thorough. It takes time. It works.

Why do scale-up founders consistently hire the wrong salespeople?

The underperformers don’t disappear from the market. HBR research shows they cycle between companies carrying the same habits, and they look perfectly credible on paper. Because their CVs are stuffed with claims nobody has ever bothered to verify. Consider who’s actually available. The top 10% of salespeople aren’t looking for work. They’re not on job boards. They’re too busy making money where they are. You’re rarely competing for the best. You’re competing for the best available. That is a meaningfully different pool. So the process has to do the sorting. You cannot rely on gut feel, a strong interview, or whether someone seemed confident on the day. You need a structured filter that rewards the behaviours you actually want, starting with the very first interaction.

Stage 1: how should you write a sales job advert that filters itself?

A well-designed job advert eliminates weak candidates before you’ve read a single CV. The covering letter test is the simplest filter I know, and it costs nothing to implement. I always ask candidates to send a covering letter with their application, setting out specifically how they’d put their skills and knowledge to work in the role. If I receive a CV without one, I decline it immediately. They haven’t read the advert properly, or they couldn’t be bothered. Either way, they’ve told me something important about how they approach work. Salespeople who read carefully and follow instructions are worth talking to. The ones who spray their CV at every open role without reading the advert are not. They have just saved you a screening call. Before you write the advert, answer three questions honestly. Why would a talented person want to work here? What do you do that’s genuinely better than the alternatives? What are the real development opportunities? If you cannot answer these clearly, you will write a dull advert and attract dull candidates.

Stage 2: what are you actually looking for when you screen sales CVs?

A CV tells you more than experience. It tells you whether someone gives a damn about how they present themselves. Look for clean formatting, no typos, and a specific explanation of why they have applied for this particular role. Vague and generic is a personality trait, not just a formatting issue. Pay close attention to target achievement. Almost every CV claims the candidate hit their targets. Given that 85% of salespeople underperform, most of these claims are either exaggerated or false. The top performers put their actual over-achievement in their CVs. They’re proud of it. They want you to know. Anything vague (“consistently met expectations”, “contributed to team success”) is a warning sign. Look carefully at the organisations they’ve worked in. A salesperson from a large, structured environment with inbound leads, a pre-built playbook, and a support team around them is a different animal from someone who has to create opportunities from scratch. If your business needs the latter, hiring the former will cost you months of frustration. The hamster wheel salesperson can run fast on a track someone else built. That’s not the same skill as building the track. Then check their LinkedIn profile. Is it up to date? Is it professional? Are they active? A salesperson who neglects their own professional presence is unlikely to use it effectively for prospecting. One more thing. Look at what they were selling before. The best sales hires tend to be people whose last product was harder to sell than yours. Someone who succeeded as the number four player in a crowded market, no brand doing the heavy lifting, will find your pitch relatively easy. Someone who coasted on a well-known logo will melt the moment they have to create an opportunity from scratch.

Stage 3: why should you use a video pre-screen before any phone call?

Before you pick up the phone, send shortlisted candidates a brief: record a short video, two minutes is enough, answering the five questions below. Give them the questions in advance. This is not a test of improvisation. It is a test of preparation and professionalism. This approach consistently cuts screening calls by between 50 and 85 per cent. Most candidates will not bother. Of those who do, assess three things: did they actually do it; how have they set up the recording (this is an interview, and the care they put into two minutes tells you exactly how much care they will take with your customers); and the quality of their answers. The candidates who make a real effort: clear setup, considered answers, asking what happens next at the end. Those are your calls. The rest are filtered automatically, without a minute of your time.

Question 1: tell me about your best deal

I got this from Jill Garrett, who ran Gallup in Europe. I leave it deliberately open. Best deal could mean the biggest commission, the most complex negotiation, or the most prestigious client. What I’m actually looking for is someone who defines their best deal by the impact it had on the customer. The deal that saved a client money. The one that solved a painful problem. The one where the customer told their colleagues about it afterwards. That’s the salesperson who sells because they believe in what they’re doing, and those are the ones who build relationships and repeat business.

Question 2: walk me through your sales process

Give them a goal: say, a million pounds of gross profit in a year. Ask them to break it down. What’s their model? What stages are in their sales cycle? How do they move prospects through? A salesperson without a defined process isn’t really a salesperson. They’re an extrovert who’s occasionally got lucky.

Question 3: how lucky are you, on a scale of one to ten?

I borrowed this from Robert Richman’s book The Culture Blueprint (2014). Successful people consistently rate themselves as lucky. Unsuccessful ones blame the leads, the product, the territory, the economy. Candidates who give you an eight, nine, or ten aren’t deluded. They’re telling you their mindset. They look for positives in difficult situations. That matters enormously in sales, where rejection is part of every working day.

Question 4: are you in the top 10% of your current sales team?

Almost everyone says yes. That’s the point. Then dig in. Walk me through your numbers. Quota, actual achievement, commission earned, total on-target versus what you actually took home. Good performers know their numbers cold. They’ll give you specific figures and be able to explain the deals behind them. If someone can’t reconcile their own compensation, they’re not in the top 10%.

Question 5: do they try to close you at the end of the call?

This one matters more than the others combined. They should be asking what the next step is, what happens from here, when they might hear back. The best candidates get on the phone with a plan. They know what they need to do to advance to the next round. If they hang up without trying to move the conversation forward, do not take them further. You’ve just seen exactly how they’ll behave with your customers. (function() { var form = document.getElementById(‘ghl-newsletter-cfe4ab65-15f5-44c9-958c-be6cfb20f1b7’); var messageDiv = document.getElementById(‘ghl-newsletter-cfe4ab65-15f5-44c9-958c-be6cfb20f1b7-message’); if (form) { form.addEventListener(‘submit’, function(e) { e.preventDefault(); var submitBtn = form.querySelector(‘button[type=”submit”]’); var originalText = submitBtn.textContent; submitBtn.textContent = ‘Subscribing.’; submitBtn.disabled = true; var formData = new FormData(); formData.append(‘action’, ‘ghl_newsletter_subscribe’); formData.append(‘first_name’, form.querySelector(‘input[name=”first_name”]’).value); formData.append(’email’, form.querySelector(‘input[name=”email”]’).value); fetch(‘https://www.monkhouseandcompany.com/wp-admin/admin-ajax.php’, { method: ‘POST’, body: formData }).then(function(response) { return response.json(); }).then(function(data) { messageDiv.style.display = ‘block’; if (data.success) { messageDiv.style.background = ‘rgba(34, 197, 94, 0.1)’; messageDiv.style.color = ‘#16a34a’; messageDiv.innerHTML = ‘Welcome aboard! Check your inbox for a confirmation.’; form.reset(); } else { messageDiv.style.background = ‘rgba(239, 68, 68, 0.1)’; messageDiv.style.color = ‘#dc2626’; messageDiv.innerHTML = data.data.message || ‘Something went wrong. Please try again.’; } }).catch(function() { messageDiv.style.display = ‘block’; messageDiv.style.background = ‘rgba(239, 68, 68, 0.1)’; messageDiv.style.color = ‘#dc2626’; messageDiv.innerHTML = ‘Connection error. Please try again.’; }).finally(function() { submitBtn.textContent = originalText; submitBtn.disabled = false; }); }); } })();

Stage 4: what exercises reveal whether a sales candidate is really any good?

The face-to-face stage is where you go beyond what candidates say about themselves and start to see how they actually operate. You also run through all five questions from the video pre-screen again in person. Three exercises do the rest of the sorting.

What does the drawing exercise reveal about a candidate?

Give them a blank sheet of paper, some coloured pencils, and ten minutes. Ask them to draw what motivates and inspires them. This sounds odd. It works. If the picture is flat and lifeless, the person probably is too. If it’s rich, specific, and tells you something about what they genuinely care about, that’s a very different candidate. I’m not looking for artistic ability. I’m looking for the energy someone brings to things that matter to them. Be wary of candidates whose primary motivator is money. As Ray Kroc said: “If you work just for money, you’ll never make it. But if you love what you’re doing and always put the customer first, success will be yours.” A salesperson who’s purely money-driven will sell the wrong product to the wrong customer if the commission justifies it. That’s not someone you want representing your business. What you’re looking for is missionaries, not mercenaries. Missionaries care about what they’re selling and who they’re selling it to. Mercenaries care about the commission. Mercenaries can hit a number. Missionaries build a business. This is also why commission-heavy compensation plans tend to attract the wrong people. For more on that, read why we don’t pay sales commission.

Which psychometric tests should you use when hiring salespeople?

Run the Gallup Strengths Finder to understand whether the candidate has intrinsic drive and self-motivation. In a scale-up environment, you need people who get on with things without being supervised every day. A verbal and numerical intelligence test is also worth running. It’s a quick, objective check on whether they have the cognitive capability the role requires.

How should the presentation test work in a sales interview?

Set a deliberately bland brief: why this company, and why you as an individual? Ten minutes. You’re not looking for a polished deck. You’re looking for someone who has practised, manages their time, doesn’t bore the room, and can present with energy and clarity. I’ve interviewed people who couldn’t use PowerPoint, people who talked for fifteen minutes when I asked for ten, and people so flat I had to stop myself checking my phone. Those people are unlikely to walk into a client meeting and make a compelling case for your product.

How do you assess whether a salesperson will keep improving?

Ask how they’re getting better at sales. Are they reading? Listening to podcasts? Taking courses? Mastery is one of the core drivers of sustained motivation. If sales is their profession, how are they pursuing it? Great salespeople are always working on their craft. Mediocre ones just turn up and hope for the best. See also: why Simon Sinek is fundamentally wrong. A useful counterweight to the usual motivation frameworks.

How do you test whether a candidate is coachable?

Give some feedback on their presentation mid-interview. Ask them to redo part of it incorporating what you’ve said. Can they absorb advice quickly and act on it? This is one of the clearest signals of future performance you’ll see inside an interview room.

Stage 5: how do you make the final decision between sales candidates?

Before making an offer, let your finalists spend time with the team they would be joining. The candidate sees what they are actually walking into. The team forms a view. And you get another set of eyes on someone who is going to be in that room every day. Do not skip this. Some people interview brilliantly and land badly. The most important rule: never hire after seeing only one person. See at least three at the final round. You do not know what great looks like until you can compare. Every time I have broken this rule, I have regretted it. Every time I have run a proper comparison, I have made a better decision. No exceptions. Before extending an offer, I apply a 50% rule: every hire must beat at least half of your existing sales team. If they cannot, you are not maintaining quality. You are making a deliberate decision to reduce your average talent density. Own that choice, or pass on the candidate. When your team is fewer than five people, hold a harder standard still: the hire should be better than your current best. At that size, a single person reshapes the entire culture and average. If you would not back this person to outperform 50% of the room, do not hire them. One final gut check: would you buy your own product from this person? Forget the LinkedIn profile. Forget where they worked. If you watched them through this process and thought “I would trust them with my leads, my customers, my best deals”. That is your green light. If you are uncertain, that is your answer. This process might feel involved for a single hire. It should. This is the person who is going to make you money, or cost you it. The time you invest upfront is a fraction of the time you will spend managing a bad hire out. As W. Clement Stone put it: “Sales are contingent upon the attitude of the salesman, not the attitude of the prospect.” Jeanne DeWitt Grosser, who ran Stripe’s go-to-market for nearly a decade, put it this way: “Yeses are great, nos are great. Maybes will kill you.” That applies to candidates as much as deals. If you finish the process and you are not sure, the answer is no. Get the hiring process right and everything else becomes easier. Get it wrong and no amount of training, territory planning, or sales ops will save you. For more on building a high-performance commercial function, read why we do not pay sales commission. Hiring right is step one. Getting the incentive structure right is step two.

Frequently asked questions about hiring salespeople

How do I verify whether a salesperson actually hit their targets?

Ask them to walk you through their numbers in detail: their quota, their actual achievement, the commission they earned, and their total on-target earnings versus what they actually took home. There is almost always a gap between what candidates claim and what the payslips would confirm. Good performers know their numbers cold. They can tell you exactly what they sold in Q3 last year, why Q4 dipped, and what they changed in Q1 to recover. They give you specific deals, specific customers, specific figures. If someone gives you vague answers, rounds everything up, or can’t explain the gap between their headline number and what they were actually paid, treat it as a significant red flag. The follow-up that separates top performers from pretenders: ask them to explain their worst quarter. Top performers have a clear account of what went wrong and what they did differently. Average performers blame the leads, the territory, or the economy. The pattern you’re looking for is ownership of outcomes, good and bad. Numbers don’t lie. Evasive answers about numbers reveal everything.

Should I hire an experienced salesperson or develop someone from scratch?

For most scale-ups, the better option is to hire someone with the right mindset who you can develop, rather than paying a premium for experience built in a very different environment. The top performers from large, structured sales organisations often struggle when they need to create opportunities rather than work a pre-built pipeline. They’ve been running on a track someone else laid. In a scale-up, you need someone who can lay the track. Look for genuine drive, intellectual curiosity, and the ability to learn quickly. They typically cost less, adapt faster, and you can shape them around your process rather than spending months trying to undo habits they’ve spent years building elsewhere. The signals to watch during the hiring process: do they ask good questions about your business, or are they reciting a pitch they’ve used everywhere else? Do they know their numbers in precise detail? Have they had to build anything from scratch, even early in their career? A new graduate who built a side business from zero is often a more interesting candidate than a seasoned rep who relied on a well-known brand to open doors. The question is always: can they create, or can they only convert what’s handed to them?

What is the most important thing to look for when hiring a salesperson?

Mindset. Specifically, a growth orientation combined with genuine customer focus. A salesperson who defines their best work by the impact it had on the customer, rather than what it earned them, is far more likely to build the long-term relationships that generate repeat business and referrals. Skills can be taught. Product knowledge can be acquired in weeks. The underlying attitude is far harder to change once they’re through the door: how someone thinks about customers, how they approach their own improvement, whether they define success by the commission or by the outcome for the person they sold to. Every question in this five-stage process is designed to surface that attitude. The luck question is the quickest proxy for mindset you’ll find. Candidates who score eight or above almost always have a growth orientation. They look for positives in difficult situations. They own their results. Candidates who score below six are telling you they attribute their results to external factors. The drawing exercise does the same work differently: what someone draws when asked to show what motivates them is more revealing than anything they say in an interview. The energy in that drawing is a direct read of the energy they will bring to your customers. The founders who follow this process hire well. The ones who short-cut it know exactly where they went wrong.

Four ways to take this further

Book a call. If you keep hiring salespeople who underperform, the process is the problem. Grab the book. Mind Your F**king Business covers the full commercial playbook: how to hire, develop, and structure a sales team that doesn’t depend on one or two star performers. Subscribe to the newsletter. Free tool every week. The kind of practical interview process detail in this post, straight to your inbox. Download the toolkit. The full toolkit includes a job scorecard template, a high-converting job advert guide, a CV scoring framework, and Topgrading interview questions tailored to sales roles. Free. Download it here. Your move. Build the filter. Run three candidates through it before you make the call. You’ll wonder how you ever hired without it.