As SimpleDocs Acquires Law Insider, Founder Preston Clark Shares the Strategic Vision

Nov 5, 2025

Preston Clark, founder of SimpleDocs and Law Insider, dives into the strategic acquisition that merges AI contract automation with a vast database of contracts. He reveals why both companies were built separately and the unique synergy behind their union. Clark explains how workflow-specific tools can elevate contract automation accuracy. He also shares plans for integrating Law Insider’s data into SimpleDocs and his vision for expanding into new legal workflows, positioning his companies as top contenders in the competitive landscape.

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INSIGHT

Deliberate Dual-Build Strategy

Preston built Law Insider as a public contract database and later created SimpleDocs as an enterprise AI product to pursue a long-term integration vision.
He intentionally kept them separate to preserve different team DNA before reuniting them when AI made the combination compelling.

INSIGHT

Workflow-Specific AI Wins Precision

SimpleDocs aims to differentiate by configuring AI to exact workflows and playbooks rather than offering generic LLM outputs.
Law Insider's precedent data lets SimpleDocs benchmark clauses and contracts against market standards for more precise guidance.

ADVICE

Configure AI To Your Exact Process

Configure AI to mirror your exact process, including approves, fallbacks, and standard comments to gain real ROI.
Use playbooks and workflows to convert AI outputs into reliable, repeatable legal decisions.

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If content is the raw material of generative AI, it only makes sense that an AI-driven contract automation platform would want to acquire the world's largest database of contracts and clauses. That is exactly what happened recently when SimpleDocs, a company with an AI contract drafting, redlining and review platform, acquired Law Insider, which claims to be home to 5 million contracts and 20 million clauses spanning more than 50 languages.

One aspect of this acquisition that makes it particularly interesting is that both companies were founded by the same person – and that person, Preston Clark, is our guest today. In that sense, you might say this isn't a typical acquisition story, but more the deliberate convergence of two complementary businesses that were built separately over more than a decade, each with its own DNA, but always with an eye toward this eventual combination.

In an AI market increasingly criticized for being "just GPT wrappers," Clark and his team are betting that workflow-specific tools powered by real contract data will deliver the precision and ROI that legal departments and law firms are demanding.

In our conversation, Clark walks us through the strategic thinking behind this acquisition and how this combined entity plans to differentiate itself in an increasingly crowded legal AI market. He also shares his vision for the future – one that extends beyond contract drafting and review into adjacent workflows that could reshape how legal teams interact with contracts altogether.

Thank You To Our Sponsors

This episode of LawNext is generously made possible by our sponsors. We appreciate their support and hope you will check them out.

Paradigm, home to the practice management platforms PracticePanther, Bill4Time, MerusCase and LollyLaw; the e-payments platform Headnote; and the legal accounting software TrustBooks.
Briefpoint, eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner).
Eve, taking care of the tasks that slow you down so you can operate at your highest potential

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