AI SDR Learnings, Results, and ROI - with Jacco van der Kooij, Winning by Design artwork

AI SDR Learnings, Results, and ROI - with Jacco van der Kooij, Winning by Design

AI to ROI

March 2, 2026

In this episode, our host Ray Rike sits down with Jacco van der Kooij, founde and CEO, Winning by Design, to discuss the real-world deployment of "Jack" - an AI SDR that has spent the last 12 months redefining the front line of Go-To-Market (GTM) strategy.
Speakers: Ray Rike, Jacco van der Kooij
**Ray Rike** (0:08)
Welcome to today's episode of the AI to ROI podcast. Today, I am joined by Jacco van der Kooij, the founder and CEO of Winning by Design. We'll be covering three main topics with Jacco today. Number one, the catalyst for their AI project within Winning by Design. Some of the initial hypothesis to justify that initial budget. And then we'll be talking about the measurements that Jacco and his team used to say, this was a great investment and here's the ROI. So that Jacco, would you please take a moment to give a brief background of your journey to becoming my guest here in the AI to ROI podcast?

**Jacco van der Kooij** (0:50)
Ray, welcome. How are you? How are you doing? And it is the first time we're speaking in the new year and we should be careful with that because it's already February, Ray. We're already 10% down of the year.

**Ray Rike** (1:01)
It's amazing. Time flies so quickly, especially AI time.

**Jacco van der Kooij** (1:05)
Oh, you better believe it. You know, if anything, what AI does, it makes things go faster. Well, it's a pleasure and a treat. I'm here today because I'm here to share some of our experiences that we had with our AI SDR. And I, you know, like I obviously, you know, embrace the opportunity to share with your listeners that what we go to in the hopes that they can benefit from it in whatever form and shape it serves them.

**Ray Rike** (1:27)
Well, I'm looking forward to this because once upon a time, someone said, Ray, you don't know Jack. And then I'm like, I do know Jack. It's an AISDR that Winning by Design is deployed. So why don't we start at the beginning? Can you tell us a little bit about kind of why you decided to go down this AISDR journey?

**Jacco van der Kooij** (1:50)
Yes. Well, as you know, and as some of your listeners may know, Winning by Design, a company I founded over 15 years ago, we help companies with the GTM motions. In the early, in the mid 2015-16, SDR was the hype, you know, later on it became process and so on. And today obviously AI is where most of the motion is. So we believe that if you deploy a technology like AI, you actually have to use it. We can't recommend it in such a new world if we're not having tried it ourselves. Now we wanted to figure out what role would we do, right? What is the right role to try it out in a customer facing role? And we picked the SDR role because it's the most, arguably, one of the highest risk roles. It leads to first impressions, trust, empathy, all that comes from that. And any form of failure instantly could damage the brand and also our pipeline. So we thought to ourselves, if AI can't work here, then it can't work anywhere. But the opposite is also true. If it can work here, it can work anywhere.

**Ray Rike** (2:50)
Jacco, do me a favor because the AI and ROI audience, it has expanded beyond the B2B tech industry and includes people from financial services, manufacturing, et cetera. Can you just explain a little bit about what that SDR role is and why it's been so critical in the B2B tech industry?

**Jacco van der Kooij** (3:08)
Yeah, the role is so critical because in most cases, it's the first point of contact that a company has with your company in which there is a form of a significant value exchange. For example, the invitation to a workshop or the sending of a reasonable research paper. So it's that first point of contact between the company. Now, the SDR generally is a person earlier on in their career that performs the pre-work needed for a sales call.

**Ray Rike** (3:39)
Great. And in the tech industry, we've been using these sales development representatives for about 10 years. And things like cadence software from an outreach, et cetera, really made it even more popular. But I know that companies are having some challenges with the performance. What were some of those business objectives or challenges that you were trying to address by using AI?

**Jacco van der Kooij** (4:01)
Yeah. Well, the first step is to realize that the ROI on those SDR functions had had starkly declined over the past years. In other words, where previously in SDR would set up about 20 appointments for a seller a month with the certain conversion rate would make it make sense. That drop has significantly dropped over the years to about three to four appointments per month. At which point in time the ROI of an SDR no longer was as valuable as it once was.

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