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:

Follow Along:

The origin story of Harvey and how it became the “Dallas Cowboys of Legal Tech”

Lessons from the early days of AI at Google Brain and DeepMind

Why the real opportunity isn’t automation — it’s amplification

How top law firms are already using AI for high-level strategic work

The emerging hybrid model of AI + human legal reasoning

Why firm size and structure could shift dramatically in the next decade

Rethinking ROI: morale, retention, and client trust as key performance drivers

How Harvey is helping firms pitch, collaborate, and win new business

The future of AI-first law firms — from pricing models to client partnerships

References:

https://www.artificiallawyer.com/2025/09/03/eudia-opens-ai-augmented-law-firm-for-ma/

In this episode, Zach interviews Tara Waters, founder of TLW Consulting and former Chief Digital Officer at Ashurst, who led the firm’s rollout of Harvey. They discuss Harvey’s meteoric rise in legal AI, Tara’s firsthand experiences adopting Harvey within a global firm, and how legal teams evaluate AI tools. The conversation explores why lawyers initially gasped at Harvey’s capabilities, how expectations have matured, and what true digital transformation in law might require. Tara emphasizes that law firms should rethink their entire business model and workflows rather than just choosing a tool.