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

🎙️ Episode Overview

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. Jacco shares the "AHA" moments and hard truths discovered while moving beyond human constraints like slow response times and inconsistent qualification. Discover how treating an AI SDR (agent) as a "system" rather than a "product" initially led to 2,030 conversations, 100% CRM capture, and a $200,000 deal.

📊 Key Topics Covered

• Breaking Human Constraints: The project addressed critical issues like burnout, limited global coverage, and poor CRM hygiene that even the best human reps struggle to maintain.

  
  

• The "AHA" Moments: Jacco details how the team realized Jack shouldn't just "chat" but perform industrial-scale qualification while supporting buyers in their buying journey.

  
  

• The Power of Iteration: Initial surprises, such as a low 8% email capture rate, were overcome by designing a better "value exchange" rather than just tweaking prompts.

  
  

• Tangible Results: After refinement, email capture jumped to 20%, MQL conversion rose by 36%, and the system successfully captured nearly 9,000 SPICED answers.

  
  

• The Ultimate Do’s and Don’ts: Success requires anchoring the agent in a GTM system and iterating weekly; failures stem from treating AI like an unstructured chatbot or deploying without clear ownership.