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

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.

Episode Summary

Winning by Design set out to prove that if AI can handle the high-risk, high-empathy role of an SDR, it can work anywhere in GTM. Over the course of a year, their AI agent, Jack was built on a foundation of 1mind logic and Clay enrichment. The agent evolved from a simple chatbot into a trained GTM operator.

Key Highlights:

• 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.

The Do's

• Design the value exchange first: Ensure the AI provides something useful to the buyer before asking for information
• Earn the next step: Focus on providing enough value to merit the next stage of the conversation
• Anchor the agent in your GTM system: AI should scale a pre-designed, structured system rather than an improvised process.
• Start narrow, then expand: Focus on one specific motion and one outcome before attempting to scale.
• Iterate weekly: Small, frequent changes to the system drive the most significant gains in performance.
• Focus on the buyer's journey: Design the experience to help the buyer buy, rather than just helping the seller sell.

The Don'ts

• Treat AI like a chatbot: Avoid unstructured "chatting," as it kills conversion rates; focus on industrial-scale qualification instead.
• Chase volume over quality: Remember that activity is not the same as a healthy pipeline.
• Hide the AI behind humans: Be transparent about using an AI agent to build trust with the buyer.
• Deploy without ownership: AI implementation is a Go-to-Market responsibility, not just an IT project.
• Expect AI to fix a bad process: AI will not fix poor GTM design; it will only expose and amplify existing flaws.
• Point AI at unstructured data: Do not simply point the AI at a massive folder of research; start with specific, high-quality training materials.

If you are considering deploying agentic AI into your Sales organization and process, this episode is full of great insights, experiences, and measurements for your AI investment in Sales.

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