How to Buy Legal AI
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Legal teams have more AI software options than ever before. Choosing between them has never been more complicated.New legal AI companies are emerging quickly. Established legal technology vendors are releasing new AI products and capabilities. And the technology itself continues to evolve, making vendor evaluation feel like a moving target.
In How to Buy Legal AI, Preston Clark and SimpleDocs CTO Jordan Trevino will walk through a practical framework for evaluating legal AI software—from defining requirements and assessing vendors to building the business case and running an effective pilot.
Preston brings the perspective of both a former in-house counsel and a longtime legal technology founder, while Jordan will address the technical, security, data, and implementation considerations that increasingly shape legal AI purchasing decisions.
What We’ll Cover
Defining the problem first
How to identify the work you actually want to automate or accelerate before evaluating technology.
Choosing the right evaluation framework
Why a focused AI tool designed for a narrow task should be evaluated differently from software intended to support broader legal workflows.
Evaluating vendors and technology
How to think about capabilities, integrations, data privacy, security, technical architecture, and vendor maturity.
Building the business case
How to connect legal AI investments to measurable improvements in efficiency, quality, capacity, and business outcomes.
Designing trials and pilots
How to structure an evaluation that tests real workflows, produces useful data, and gives stakeholders confidence in the decision.
Making decisions in a rapidly changing market
How to compare emerging AI-native vendors with new products and capabilities from established legal technology companies.
The goal is not to identify a single “best” legal AI product. It is to give your team a repeatable framework for determining which technology is best suited to your requirements, budget, risk profile, and workflows.
About the Host
Preston Clark is the CEO and co-founder of SimpleDocs, an AI-powered contract automation platform that helps legal and business teams draft, review, and manage contracts more efficiently. He is also the co-founder of Law Insider, the world’s largest public contract and clause database, serving thousands of legal and business professionals worldwide.
With more than 15 years of experience at the intersection of legal operations, software, and AI, Preston has built and scaled products focused on modernizing how contracts are created, negotiated, and managed. Prior to becoming an entrepreneur, he held leadership roles at several venture-backed startups and served as Assistant General Counsel at the University of Miami.
Jordan Trevino leads product and engineering for SimpleDocs, used by large multinationals and public companies. His goal is to reduce friction, cost, and cycle time in high-volume legal workflows while preserving control, auditability, and security.
Based in San Francisco, Jordan is a successful entrepreneur and software developer. He leads a team of highly skilled engineers and designers in Mexico City