The Legal + AI Handshake

In this session, we summarize:

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_00:30 Sabrina sets the stage for a real-world case study on implementing AI in-house, grounded in lived legal experience rather than theory.

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_01:58 Charlie explains joining Credit Spring as the first legal hire and inheriting a contract landscape with no visibility, ownership, or documented process.

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_02:54 How the legal tech evaluation process quickly became overwhelming, and why Credit Spring narrowed focus to just two clear, outcome-driven criteria.

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_04:21 Sabrina highlights a critical lesson: defining use cases upfront helps legal teams cut through a crowded, feature-heavy legal tech market.

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_05:10 Charlie walks through running a controlled pilot, avoiding “perfect demo contracts,” and testing the tool against real, messy agreements.

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_06:18 Why Credit Spring kept the pilot legal-only, launching quietly to prove value before introducing the tool to the wider business.

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_07:53 The biggest early wins came not from AI features, but from workflow automation: centralized intake, triage, approvals, and audit trails.

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_08:24 Moving away from emails, Slack pings, and desk walk-ups to a single source of truth dramatically improved visibility and efficiency.

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_09:07 Playbooks enabled faster first-pass reviews, helping legal surface risk earlier and guide business teams before deep negotiations began.

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_10:02 Sabrina reframes ROI beyond time and cost savings, highlighting how uncovering previously hidden contractual risk delivers real business value.

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_10:56 Charlie explains how AI and structured workflows shifted legal’s role toward being more data-driven and impact-focused.

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_11:33 Measuring risk reduction over time allowed the legal team to quantify value that was previously invisible to the business.

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_12:21 Addressing the fear of AI replacing lawyers, Charlie emphasizes AI as a support system that removes low-value churn, not legal judgment.

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_13:04 By accelerating routine work, AI created “more thinking time” for complex, high-impact legal matters.

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_14:33 Demonstrating ongoing ROI helped rebuild business confidence after initial slowdowns caused by introducing proper legal processes.

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_15:52 Charlie explains why contract speed initially dropped, and how transparent data helped reset expectations and show long-term gains.

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_17:29 Self-serve templates and tiered workflows enabled low-risk contracts to move faster while preserving legal oversight.

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_22:09 A key takeaway: don’t buy a tool that does everything: buy a tool that solves your most painful problem well.

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_23:00 Charlie reflects on implementation challenges and the importance of responsive vendor support to drive successful adoption.

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_24:30 Closing reflections on how introducing structure and tooling helped legal move from reactive to trusted business partner.

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“AI hasn’t replaced legal judgment; it’s removed the low-value churn so we have more thinking time for the work that actually matters.”

- Charlie Cairns, Head of Legal, Creditspring
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