Winning by Design: An Honest Review from Someone They Trained in 2017

Full disclosure before any opinion: my sales team was one of the first in the Benelux to receive Winning by Design training, back in 2017. The Dutch ecosystem has always had a strong link to them, founder Jacco van der Kooij is Dutch, as was his co-founder, so they were around a lot in the early days. I've followed the company ever since, stayed in contact with people who were there from day one, did their CRO school, and worked through their content. So this is a review from inside the tent, not a drive-by.

This is for the founder, VP of Sales, or enablement lead weighing up whether to buy Winning by Design training, and wondering whether the methodology lives up to the reputation. The short answer is that it mostly does, with two important caveats.

1What Winning by Design Got Right

Let me start with the credit, because it's substantial. When my team was trained, Winning by Design confirmed a lot of what we were already doing well and, crucially, gave us a language to talk about it. Once you can name what you're doing and why, you can improve it deliberately. That's a real gift.

Zoom out and the contribution is bigger than any one team. Winning by Design tried to give the SaaS world a blueprint and a common vocabulary: consistent definitions of an SQL, of the conversion rates between stages, of the customer journey through the Bowtie model. Suddenly things became comparable. Through their work with communities like Pavilion (the old Revenue Collective) and their CRO school, they associated a large number of companies with the methodology and effectively set it as the gold standard for B2B SaaS. That isn't just good for them. It's good for every VP of Sales who can now compare notes with a peer and know they're speaking the same language.

So, net positive, full stop. The rest of this review is about where the standard offering struggles, not about whether the thinking is good. The thinking is excellent.

2The Teaching Problem (Which They've Partly Fixed)

The training I received in 2017 was, in practice, an eight-hour, nonstop download of information and theory with a bit of homework. For me it was great, because I was hungry to learn. But as I heard firsthand from the trainers themselves, it was not very effective at helping the average motivated rep, simply because it was too much knowledge transferred at once.

Credit where it's due: they've since broken the courses into smaller, more intensive sessions focused on individual elements, which is a real improvement. The company's centre of gravity has also shifted, away from one-off seat-based courses and toward in-company trajectories for larger organisations, acting as an embedded enablement and training partner. That makes complete sense for them commercially. It also quietly tells you something about who the standard product is now built for.

3The "Sales as a Science" Over-Engineering

Here's my first real critique. Winning by Design has both captured and amplified a trend: sales leaders increasingly want to treat sales as a science. I'm a supporter of that in principle, I have an academic background, and as Jason Jordan and Michelle Vazzana argue in Cracking the Sales Management Code, the best sales managers have a scientist-like attitude, genuinely hunting for the root cause behind a skill gap.

The problem is the tipping point. Rather than making sure teams can actually sell, a lot of organisations end up running the equivalent of Monte Carlo analyses on every metric, chasing statistical insight about the state of the funnel. It over-engineers the sales-management role to suit a new breed of B2B SaaS manager, a more data-driven, "blue" profile, rather than the people-first manager of old. Data-drivenness isn't bad. You need it. But it's been allowed to crowd out the unglamorous work of skill development.

That's the core risk. The standard Winning by Design program can leave you expecting reps to be fully mature with the least possible investment in their actual skill. The frameworks are the bodywork. The engine is whether your reps can run a real discovery call on a Tuesday afternoon, and that gets built through coaching, not definitions.

4The Price and Alignment Problem

This is where it gets practical for a European company. I paid around $1,250 per person in 2017. Today the open Revenue Academy courses run roughly $2,500 per person, and private, in-company training, what they aptly call shared language and standards, starts around $40,000 per team and goes up from there.

I'm not disputing the expertise behind those prices. My issue is fit. For the average European company, banking on the open courses has two problems. They're expensive on a per-person basis, and, more importantly, they aren't aligned to where your reps actually stand. You get no overview, and no guarantee that what a rep sits through is relevant to them or absorbed rather than experienced as just another webinar.

The private courses solve the alignment problem, which is exactly why I'd advocate for that format. But at $40,000 per team and up, it's hard for an averagely funded European B2B SaaS or AI company to take seriously as an option. So you're caught between an affordable product that isn't aligned and an aligned product that isn't affordable.

5SPICED Is Not the One Framework to Rule Them All

My second critique is about SPICED itself. It's often presented as the single qualification and discovery framework that rules them all, and that's where I push back. SPICED borrows heavily from SPIN selling, with elements of other methodologies layered in to handle the deal-management process. As I argued in my comparison of MEDDPICC and SPICED, SPICED genuinely helps teams through its simplicity, and it's a strong fit for lower-to-mid-range ARR B2B SaaS.

But simplicity has a cost. SPICED lacks nuance on the complexity of pain and impact: it doesn't push reps to assess the novelty of a pain (is this something the buyer hadn't yet framed?) or its altitude (is it an executive priority or a single user's nuisance?). And it's thin on depth elsewhere, on exploring the competitive situation and on identifying the right champion. Presented as the one discovery framework, it quietly under-serves complex deals.

Winning by Design is, in a sense, a slave of its own success. Standardization helps the ecosystem, but the individual company demands far more nuance in its go-to-market than any standardized training can give.

The open courses, by design, don't deliver that nuance. The private courses might. But that takes us straight back to the price-and-fit problem above.

So Where Does That Leave You? Alternatives Worth Weighing

To be clear one more time: I recommend Winning by Design and I commend their thought leadership. But to avoid the Ferrari-with-a-Fiat-motor outcome, you want private-course-style tailoring at a price that's actually viable. That's the lens for considering alternatives.

1. A tailored, baseline-first approach

This is what I do, so weigh it accordingly. I treat every training as a mini consulting project: before teaching anything, I dig into how reps actually run calls, what the KPIs say, and what the outbound emails look like, then build a blueprint I refer back to throughout the training. That keeps the same language as the reps and earns their buy-in, because they see immediately that the topics are relevant to their real week. In the longer sales-coaching (sales excellence) trajectory, I run a baseline analysis of every rep and manager to find the skill gaps holding back win-rate and ARR growth, then set the team-wide training focus on the common denominators and individual coaching on the rest. It's tailored by construction, which is precisely the thing a standardized program has outgrown the ability to do.

2. Winning by Design's own private trajectories

If budget allows, their in-company team training is the version I'd actually choose over the open courses, because it solves the alignment problem. Just go in expecting the $40,000-and-up commitment.

3. Corporate Visions

I'm a fan of their work too. They've taken a similar, science-leaning path, defining the Challenger Sale and Challenger Customer principles with a lot of rigour. But they fall into the same trap as Winning by Design: standardization at the expense of the customization that makes training and coaching actually stick.

A Standard Worth Learning From, Not Always Worth Buying As-Is

Winning by Design earned its reputation, and I'd never tell a team to ignore their frameworks. But frameworks are the easy part. The hard part is turning them into reps who can actually run the call, and that's a coaching problem a standardized course can't solve for you. If you want the tailoring of a private engagement without the enterprise price tag, that's exactly the gap my work is built to fill.