Masterclass: build & manage your (first) sales team
Maarten Laruelle David Du Pré built sales teams at Showpad and Alan. Now he’s co-founder of WARREN (keep an eye on them!). Last night he gave a masterclass at Winter Circus on building your first sales team.
I was there to learn — not because I’m building a sales team, but I’ve been there and wanted to get his take. An interesting parallel with pricing I noticed: most founders are solving the wrong problem at the wrong stage.
Start with belief systems, not playbooks
David opened with a visualization from The Good Ancestor by Roman Krznaric. Fifty thousand years back: all the dead, tiny gray dots. Us, the living: 8 billion people, a small green speck. Fifty thousand years forward: 7 trillion people yet to be born.
His point wasn’t philosophical fluff, it was a hiring filter. A bit abstract I must say, but I get it.
When you tell this kind of story in an interview, some people light up. They get that building something is a vote for a future that doesn’t exist yet, and others roll their eyes. Both reactions are useful information.
The people who light up? Those are your missionaries. The ones who roll their eyes? Mercenaries. And in the early days, you only want missionaries.
Missionaries vs mercenaries
Mercenaries ask these questions in interviews: What’s my territory? Who’s my solution engineer? Who does my demos?
He shared a painful example. He once hired a top performer from the Nordics. First question on day one at the office: “Who’s my solution engineer?”
The wrong person at the wrong stage. That hire was used to a mature organization with support structures. The company wasn’t there yet.
Missionaries are different. They want to sell the future, they build culture as they go and they understand there’s no playbook yet — and that’s precisely why they want in.
The sanity check: where are you really?
Most founders think they’re further along than they are.
David used Mark Roberge’s (HubSpot, Stage 2 Capital) framework, but he added his own twist. Three stages: product-market fit, go-to-market fit, and scaling. Most people in the room thought they were in scaling. David wasn’t convinced.
Product-market fit isn’t about closing your first customers. It’s about retaining them. A lot of founders close 5-10 deals through their network, hit 200-300K in revenue, and declare product-market fit. But if those customers churn within a year, you never had it.
Go-to-market fit means you’ve found repeatability. At least one demand generation channel works. You can explain the process to someone else and they can execute it.
Scaling is when you can actually accelerate. Playbooks are mature. You can afford to hire passengers, not just drivers.
The mistake everyone makes: starting initiatives that belong to a later stage. Running multi-channel campaigns when you don’t yet know why customers stay. Hiring enterprise reps when you’re still figuring out your ICP.
Leading vs lagging indicators
Churn is a lagging indicator, because by the time you measure it, it’s too late.
The question is: what leading indicator predicts churn?
David’s example: if a customer doesn’t log in within six months, or doesn’t activate a specific integration, they’re going to churn. You know this in advance, but if you only measure churn, you only see it when they’re already gone.
This applies to every metric. Find the leading indicator and manage that.
Drivers vs passengers
This was the part that resonated most.
In the early stages, you only want drivers. David described them clearly: they look for problems and solve them. They clarify things that are unclear, even outside their scope. They inject energy.
Passengers wait for instructions. They stick to their defined role. They drain energy.
Later, in the scaling phase, passengers are fine. You have playbooks, you have structure. But in product-market fit and go-to-market fit? Passengers will kill you.
This reminded me of a framework I learned from Jurgen Heyman at SPI: the distinction between eagles, journey people, and laggards. Eagles are the top 16% of salespeople, the ones who far exceed their targets and typically generate 50 to 80% of total revenue. Journey people are the middle two-thirds, good for 20 to 50% of revenue. Laggards are the bottom 10%, barely contributing.
The interesting part is what defines an eagle. It’s not personality type. It’s five learnable attributes: knowledge of capabilities (what they do for the customer, not what they are), situational knowledge, people skills, selling skills, and a collaborative attitude where the buyer’s interests come first.
David’s driver/passenger distinction maps onto this. Drivers are potential eagles. Passengers are at risk of becoming laggards. And the good news from SPI’s research: all of those eagle attributes can be trained. But only if you start with a driver.
David’s advice: look at your current team through this lens. You don’t need to act immediately, but you need to see it clearly.
The three hiring traps
David was transparent about his own mistakes.
First trap: not going deep enough. He once hired three top performers: number one at Box, number one at LinkedIn Benelux, number one at DocuSign Benelux. Killer team, right?
Total failure.
He’d asked the right questions. “Do you like outbound?” Yes. “What percentage of your deals were outbound-sourced?” 90%.
But he forgot one question: “How many calls did you have to make to get one qualified opportunity?”
At LinkedIn: 20-30 calls. At Showpad: 100+ calls for maybe one opportunity.
The calibration was completely off. Within three weeks, the new hire called: “This isn’t working.”
Second trap: hoping things will work out. You see orange flags but ignore them because you like the person and are convinced you can coach them.
It doesn’t work.
Third trap: speed over quality. If you need the hire to meet your capacity plan, you will fill the seat with the wrong person.
Everyone knows this is expensive and most of the time more expensive than not hiring, but still everyone does it anyway.
The 12-month failure question
This was David’s most powerful hiring tool. He shared it publicly for the first time.
“Imagine 12 months from now, we both agree our collaboration isn’t a success. If we asked the people who know you really well, what would they say was the main reason?”
Why does this work? They have to think on their feet. It’s not “what are your weaknesses,” but it feels like it. They become vulnerable in a way they didn’t expect.
The red flag: if they externalize the reason. If it’s the company’s fault, or the market’s fault, or their manager’s fault. That tells you they’re a passenger, not a driver.
David’s tip: ask this question to your current team too. You’ll learn things you didn’t know.
Functional fit vs emotional fit
This was the example that hit hardest from a pricing perspective.
David worked with Henchman, the legal drafting tool. They always sold on “productivity gains” and “time savings.” Functional fit.
The problem: the pain wasn’t sharp enough to accelerate deals.
They changed one question: “Can you explain why you’re looking into a solution like this, and how it links to your business priorities?”
The answer surprised them.
A law firm explained: “We grow in two ways. We add practice groups, or we do M&A. When we acquire a company, we want them to draft contracts in our signature style. We struggle with that. We’re looking at tools like Henchman to solve this problem.”
Suddenly the conversation wasn’t about features. It was about a blocker in their M&A strategy.
The impact: higher contract values, faster deals, deeper relationships with large law firms.
David didn’t frame this as a pricing insight, but I couldn’t help seeing it through that lens. When you sell on functional fit, you’re essentially selling features. Time savings. Productivity gains. The problem is that features are comparable. Your competitor can match them, often within months. And when features are comparable, you’re in a commodity game. Price becomes the deciding factor.
Emotional fit is different. When you connect your product to a business priority, something specific to that customer’s situation, you’re no longer selling a tool. You’re selling an outcome. And outcomes are hard to compare. How do you put a price on removing a blocker in your M&A integration process? You don’t compare it to what other drafting tools cost. You compare it to the cost of the problem itself.
That’s where pricing power comes from. Not from having better features, but from being connected to something the customer actually cares about at a strategic level.
The M System
David closed with his own framework, what he calls “The M System.” It’s a matrix that maps four elements across the three stages.
Mobilizers, Movement, Multipliers, Moat. Each one means something different at each stage.
In product-market fit, you’re the mobilizer. Your signal is founder-led. The movement is a learning motion. Your multiplier is network leverage. Your moat is you, the founder.
In go-to-market fit, you have a codified playbook. The movement becomes repeatable. You go deep in one channel. You’re building toward a real moat.
In scaling, you own the category. The movement is segmented execution. Multipliers become force multiplication. The moat compounds.
The homework he left us with was simple:
One: Write your belief system in a few sentences. Not the mission statement. The real one. The thing that makes a missionary say yes immediately and a mercenary feel nothing.
Two: Do you know where you are? Are you doing the right things, or doing things right?
Three: Look at your current team. Driver or passenger? Missionary or mercenary? You don’t need to act today. But you need to see it clearly. Ask the 12-month failure question.
I walked out thinking about how much of this applies beyond sales. The distinction between functional and emotional fit is a pricing problem. The distinction between drivers and passengers is a team-building problem. The distinction between leading and lagging indicators is a metrics problem.
But underneath all of it is the same question: are you solving the right problem at the right stage?
David Du Pré is co-founder of Warren and was previously VP Sales at Showpad/Alan and advisor at Henchman and many others. This masterclass was at Winter Circus in Ghent.
Selling on emotional fit but still pricing on features? Let’s talk.