Reimagining CLM: Alistair Maiden on Human-Centered Contracting in the Age of AI

As enterprises continue their digital transformation journeys, contract lifecycle management (CLM) is at a pivotal intersection of technology and user experience. Despite rapid advances in AI-enabled contracting platforms, many organizations still struggle with disengaging, manual processes that frustrate stakeholders. According to World Commerce & Contracting, poor contract management can cost businesses up to 9% of their annual revenue—highlighting the urgent need for change not just in tools, but in mindset.

How can legal and procurement leaders move beyond digital efficiency to design contracting processes that truly serve the people behind them?

In this episode of Fast Track by Icertis, host Bernadette Bulacan welcomes Alistair Maiden, Global Advisory Lead at Consilio and founder of SYKE, to explore the evolution of CLM through the lens of human-centered design. Their conversation delves into the emotional and operational pain points of traditional enterprise contracting and how generative AI, when paired with empathy, can transform the user experience.

Key Discussion Points:

  • Why contracting processes must be intuitive and human-friendly to drive real adoption

  • How AI tools are removing friction from drafting, redlining, and contract intelligence

  • The importance of identifying and learning from real-world AI superstars in legal operations

Alistair Maiden is a former contracts lawyer turned legal tech innovator. He founded SYKE to bridge the gap between legal expertise and digital transformation and now serves as Global Advisory Lead at Consilio. Recognized for his thought leadership in CLM and legal operations, Alistair brings both practical and strategic insight to the intersection of law, technology, and human experience.

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