Squared & Settled

Low Ego, High AI: CLM Skeptic to Champion

Rethinking contract management

Squared & Settled

In this episode of Squared & Settled, Sarah Irwin, CEO & Founder of ITGC, joins us to discuss how CLM skeptics become CLM champions with the introduction of agentic AI. Sarah brings a buyer's perspective, plus insights from her community of in-house leaders, to a frank conversation about what agentic AI can handle and where humans still need to step in. If you've wondered how much agentic AI can take off your plate without taking your judgment or oversight with it, this episode gives you a clear and practical answer.

Watch the episode to discover:

  • How CLM grew into agentic AI: Just three years ago, the legal tech conversation centered almost entirely on contracts. Then generative AI arrived, and now agents can take actions and reason for you. Sarah explains why that shift feels equal parts exciting and nerve-racking, and what it means for teams weighing full infrastructure against single-fix tools.
  • Building playbooks that actually get used: Learn why you should pick your single most negotiated contract type, distill the few points that always come up, and build a reusable playbook that agents can apply to your pre-approved positioning with valid explanations alongside.
  • Redlining and negotiation, with you as the final reviewer: Redlining is where AI agents do the heaviest lifting right now. Hear how an agent can recognize a third-party NDA at intake, run your playbook against it, and hand you a first pass to review.
  • The low ego, high self-awareness mindset: Technical fluency compounds like any skill, and Sarah compares it to learning piano one practice session at a time. Her advice starts small: 20 minutes of AI playtime a week, a peer forum, and the humility to admit what you don't know.
  • Evaluating agentic CLM tools: Get Sarah's guidance on how to pressure-test CLM vendors on such things as governance, data privacy, and more. Plus, hear the one question she'd ask every vendor during an evaluation.

Whether you're a GC, run legal ops, or help keep an in-house team moving, this conversation is for you. Get the insights you need to build smarter playbooks, buy with confidence, and give your team room to focus on the critical work that matters most. Watch now!

Featuring

Ashley Jones headshot
Ashley JonesSenior Counsel, LinkSquares
Sarah IrwinCEO & Founder, ITGC

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