This week we talk with Ross Guberman, founder and CEO of BriefCatch, and Heather Rodriguez, the company’s enterprise account executive. Ross built BriefCatch to put the lessons from his books and workshops in front of lawyers while they write. It started as a rules engine that flagged everything from typos to sentence flow. He admits he was never a coder, and says he would have looked for a technical co-founder if he had known the term existed. Today BriefCatch pairs that original engine with generative AI to review whole briefs, motions and judicial opinions for persuasiveness and consistency. The company has spent much of 2026 on checking how accurately briefs describe cases and statutes.
That leads to RealityCheck, BriefCatch’s citation verification tool. Heather explains that it checks whether the cited opinion supports the proposition, pulls up the relevant language and flags potential problems. An experienced lawyer can disagree with its reading, and the lawyer still owns the argument. Ross adds that running RealityCheck on briefs from the 1990s through the 2010s turns up plenty of case law errors, so the problem predates generative AI. The talk then turns to how alike AI prose sounds, and Marlene warns she may lose her mind if she reads “it hits differently” one more time. Heather describes how BriefCatch offers choices the attorney can accept or reject. Ross gives the example of lawyers who use “indicate” for everything; the tool suggests more precise verbs such as specify, convey or reflect. On Anthropic’s plan to watermark text written by Claude, Ross praises the accuracy of the AI detector Pangram. He hopes the profession will start asking a better question about AI-assisted work: was it a good brief?
Heather then describes where enterprise adoption stands. The Legal Technology Hub map has grown so crowded you need a magnifying glass to read it. Firms now ask whether a product is the best fit for a specific use case and whether it can replace tools they already own. Workflow fit, ROI and security reviews dominate the conversation, and she has seen firms that love a product spend months in security and procurement. Ross credits his reputation in legal writing with helping BriefCatch earn trust, though the company still answers the same questionnaires as every vendor. He walks through the WordRake acquisition, closed in January, which brought Gary Kinder’s conciseness and plain language technology and a new customer base to BriefCatch, and he hints that more acquisitions may follow. BriefCatch is also expanding past its Word plug-in into web apps, Outlook, an admin platform and PDF reports for courts, while Ross notes that most lawyers still do their real work in Word. When Greg asks about an MCP integration with Claude or OpenAI, Ross says one could arrive before the end of the year.
Marlene asks what is true today that wasn’t a year ago. Heather says AI has become a normal part of legal work, and hands-on experience has taught lawyers what the tools do well and where they fall short. Ross calls the weekly stream of new possibilities energizing and overwhelming, for founders and customers alike. Looking ahead, Heather expects firms to build their own AI ecosystems and pick the right tool for each stage of the work. Ross predicts that courts, which are quietly experimenting with generative AI, will use it far more within a year. Once courts signal their approval, he expects lawyers to stop debating whether to use these tools and start choosing which ones. Marlene drops off near the end with technical issues, so Greg wraps up the conversation with both guests.
Transcript
