Building the AI-First Law Firm: Jen Berrent on Covenant and the Next Era of Legal Services

Zach talks with Jen Berrent, former WeWork executive and founder of Covenant, an AI-first law firm reimagining how deals get done. They dive deep into what it means to build a law firm from the ground up around artificial intelligence — not as a tool, but as the foundation. Jen shares her perspective on why too much work still runs through Big Law, how AI is transforming the middle tier of legal work, and what it takes to balance human expertise with machine efficiency. In this episode: 00:00 – Intro: Zach on the rise of AI-first law firms. 01:53 – Introducing Jen Berrent, founder of Covenant. 02:35 – Defining an AI-first law firm vs. a firm just using AI. 04:46 – How AI impacts the operations, business, and practice of law. 06:49 – Moving beyond summaries to automated legal advice. 08:52 – What legacy tech becomes unnecessary in an AI-first model? 10:44 – Building custom client matter management (CMM) systems. 14:00 – Business model: Transactional fees vs. the billable hour. 15:47 – Why Covenant focuses on private markets and financial institutions. 19:17 – Vertical expansion: Representing LPs and venture investing. 21:04 – The shift toward self-service for in-house legal teams. 24:57 – The "dance" of negotiation and finding win-win points. 30:14 – The future of legal jobs: Judgment over processing. 34:30 – Why AI-first firms are a "once in a generation" shift. 38:34 – Competing with Big Law: Where the AI model wins. 40:27 – The "Relationship Ramp": Trust in the age of AI. 41:54 – Fundraising and execution velocity for new legal tech. 43:37 – Thoughts on the industry landscape (and Robin AI). 47:00 – Jen’s journey from Big Law and WeWork to entrepreneurship. Learn More: Zach – legallydisrupted.com Jen – https://covenant.co/about Follow Along: Zach – linkedin.com/in/zachabramowitz Jen –   / jenniferberrent   #legalai #legaltech #lawyers #legal #legalpodcast #podcast #ai