On The Record
Temporada 1
Is AI Making Legal Work Harder to Trust? Redlines, Watermarks & CLM
Is OpenAI Coming for Legal AI? Budgets, ROI & the AI Bill
por Gabby Macsweeney and Ruben Miessen
AI can rewrite a contract in seconds. But if the other side has to untangle every change, has anyone actually saved time? In this episode of On The Record, Gabby Macsweeney and Ruben Miessen discuss the gap between producing more legal work and producing better legal work. Starting with Anna Guo's critique of AI-generated redlines, they debate precision edits, negotiation friction and the responsibility to review what AI produces. The conversation moves to hidden instructions in court filings, the debate over watermarking AI-generated text, and whether frontier-model safety announcements signal responsibility, competitive positioning or both. Ruben also shares what he looks for when hiring, explains the thinking behind LEGALFLY's Contract Intelligence, and answers Gabby's question: is LEGALFLY becoming a CLM? They close with the work he delegates to AI and the people decisions he keeps firmly in human hands. Explore Contract Intelligence and join the waitlist: LEGALFLY Contract Intelligence Recorded September 8, 2026.
In this episode of On The Record, Gabby MacSweeney and Ruben Miessen discuss a busy week in legal AI. They cover Gartner’s prediction that legal tech budgets will double by 2028, why buyers should never fully trust polished AI demos, what OpenAI’s move into legal could mean for specialist legal AI companies, and why AI costs, token usage, and ROI are becoming impossible for companies to ignore. They also discuss what is happening inside LEGALFLY, including customer expansion, growth across business teams, and the company’s increasing presence across Europe, the UK, Dubai, the Middle East, and Asia. Topics covered: Legal tech budgets doubling by 2028 Why legal AI buyers need to test products with their own documents OpenAI, Codex Sites, and the future of specialist legal AI Whether companies will discover the AI bill before the ROI Legal AI pricing, LLM costs, and sustainable growth LEGALFLY’s customer success and global expansion The Pope’s comments on AI, responsibility, and human judgment On The Record is LEGALFLY’s podcast on hard news and hot takes in the world of legal and AI.
In this episode of LEGALFLY On the Record, Gabby MacSweeney is joined by Ruben Miessen to unpack the latest stories shaping legal AI. They discuss Aaron Levie’s argument that AI could create more lawyers, not fewer, and why the real shift may be in the volume and accessibility of legal work rather than headcount alone. The conversation also covers whether legal AI is becoming a two-horse race between Harvey and Legora, why law firm workflows and in-house legal workflows require different products, and what Legora’s acquisition of Qura says about the growing importance of trusted legal knowledge. Gabby and Ruben also discuss LEGALFLY’s strategic partnership with Qistas in the Middle East, the importance of local legal context, and why regional legal AI cannot rely on generic models alone. Also covered in this episode: • Why “legal AI” is likely to split into more specialised categories • What CLOC Chicago means for LEGALFLY’s US expansion • The debate around ARR, contracted ARR, and trust in legal tech growth claims • Key takeaways from LEGALFLY’s Legal AI Benchmark report • Why AI adoption is organisational change, not a one-off project • Harvey Specter, Jude Law, Legally Blonde, and the marketing arms race in legal AI LEGALFLY On the Record is a regular series covering real-world news, market shifts, and sharp takes from the world of legal and AI.