On this episode of The Vertical SaaS Podcast, host Gavin Savage sits down with Simon McCarthy, VP of Enterprise Transformation at ContractPod AI, to unpack what’s broken in Contract Lifecycle Management and what’s coming next.

With over 150 CLM implementations under his belt, Simon shares a brutally honest take on why most platforms fail, the myths around CLM as a “legal” tool, and how AI is reshaping the contract stack. From post-signature ROI to the rise of agentic contracting, he offers sharp insights into where legal tech is headed and how operators can actually get it right.

We explore:

• Why half of CLM projects fail and how to avoid becoming a cautionary tale
• The true cost of doing nothing in contract management
• What makes vertical SaaS fragile in the era of AI
• Whether “intelligent contracting” is just rebranding or something deeper
• The line between tools and platforms, and how AI could redraw it

Whether you’re scaling a legaltech product or rethinking your enterprise contract stack, this one’s packed with hard truths, practical wisdom, and a hopeful look forward.

Key Takeaways:

• Simon has led 150+ CLM rollouts across major enterprises
• Change management, not tech, is the CLM killer
• CLM is a cross-functional platform, not just for legal
• Bad implementations can cost millions in sunk value
• AI + agentic tools are transforming the CLM stack
• Real value lies after the signature, in tracking, obligations, and outcomes
• Adoption hinges on integration and user behavior, not features
• The future is modular, intelligent, and AI-native

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