E33 - 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:

• 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