Mastering context engineering in conversational AI with Martin Cross, Connect

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Kane Simms

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About this episode

In this episode, we dive into the art and science of context engineering with Martin Cross, President of Connect, a company that empowers enterprises to transform through the use of AI and automation.

Martin shares how most businesses still approach AI with a technology-first mindset, deploying solutions before clearly defining the customer problem they’re solving. He explains why successful AI experiences begin with understanding the user journey, designing the right interaction, and then selecting the appropriate tools, not the other way around.

We explore different layers of context – from session-level to journey-wide to CRM-integrated, and how they work together to transform generic interactions into deeply personalised, proactive experiences.

We also unpack Connect’s acquisition of Elerian AI and why contact centre voice recordings represent an untapped goldmine of training data. Martin explains how fine-tuning models with real-world conversations, including dialects, accents, and customer intents, can dramatically improve AI accuracy and empathy.

Additionally, we reflect on why the industry continues to repeat old mistakes and how businesses can design AI that truly understands and anticipates customer needs.

Show notes

Follow Martin Cross on LinkedIn
Find out more about Connect

Follow Kane Simms on LinkedIn
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Take our updated AI Maturity Assessment
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Kane Simms

A strategic AI advisor who, for the past decade, has helped business leaders and product owners transform customer experience using conversational and generative AI.

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