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:


What an “AI-first” law firm actually looks like


How Covenant is redesigning legal workflows from scratch


The problem with Big Law’s “too much work, too few alternatives” model


Why reading comprehension is AI’s legal superpower


Building client trust in the age of automation


How AI can accelerate deals — without sacrificing rigor


The difference between a “relationship ramp” and a “SaaS snowball”


The challenges (and advantages) of raising funding in legal AI


Lessons from Robin AI’s struggles — and why clarity of business model matters


Why this is a once-in-a-generation moment for lawyers who want to innovate


Learn More:
Zach – legallydisrupted.com
Jen – https://covenant.co/about
Follow Along:
Zach – linkedin.com/in/zachabramowitz
Jen – https://www.linkedin.com/in/jenniferberrent

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