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Watch on YouTube HERE. In the Season One finale of Contractually Speaking, Matt Patel shares two conversations recorded recently on-location in Chicago during the CLAS and CLOC events, with Gabriel Saunders and Jonathan Perkel.
Gabriel explores a challenge every legal technology provider faces: how to prioritize customer requests, feature enhancements and product innovation at scale. He shares how his team uses AI agents to automatically analyze customer conversations, identify patterns and generate actionable product insights — helping product teams reduce duplication, accelerate prioritization and improve responsiveness.
Jonathan focuses on the buyer perspective, reflecting on his organization’s CLM evaluation journey, and breaking down the real-world tradeoffs legal departments face when choosing enterprise legal technology. From integrations and AI capabilities to total cost of ownership, configurability and long-term scalability, he and Matt highlight the
Together, these conversations provide both the vendor and customer perspective on how AI is reshaping legal tech product development, evaluation and adoption.
🔑 Key Topics Covered:
- Using AI agents to manage product requests and feature prioritization
- Balancing innovation with usability and product stability
- Evaluating CLM platforms based on business needs and budget
- The importance of integrations with Salesforce and AI tools
- Configurable vs custom-coded enterprise platforms
- AI-powered contract intelligence and repository analysis
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