What happens when you've built AI infrastructure inside one of the world's top law firms and then step back to see the whole market?

In this episode, Andrew Baker, Chief AI and Data Strategy Officer at Entegrata, explains why the gap between frontier firms and everyone else is wider than most people realize. Andrew shares what looked different the moment he crossed from Simpson Thacher to the platform side, and how the variety in how firms approach AI surprised him more than he expected. His thesis: applications are transient, but data is the pinch point that everything runs through. That belief shapes how Entegrata is building both products and services to support firms at every stage of their journey.

He gets honest about what's being oversold to firms right now, why partners are coding their own AI apps on weekends, and why "nothing is off the table anymore" is something even he finds unsettling to say. Andrew also unpacks what AI-ready data actually means, why perfect is the enemy of good in data strategy, and why the first move for any firm feeling behind is simpler than they think.

Timestamps:

(00:00) Intro

(01:37) The market is more varied than expected

(04:53) Building product and services at Entegrata

(06:23) The gap between frontier and lagging firms

(08:32) Where AM Law firms are stuck today

(10:59) What's oversold vs undersold in legal AI

(14:02) Nothing is off the table anymore

(15:25) Data as the real pinch point for 2027

(18:22) What AI-ready data actually means

(29:52) The smallest first move for firms that are behind

Connect with our guest:

• Andrew Baker on LinkedIn: https://www.linkedin.com/in/andrewmichaelbaker/

Connect with Tom:

• Tom Baldwin on LinkedIn: https://www.linkedin.com/in/tombaldwin/
• Learn more about Entegrata: https://www.entegrata.com

What actually happens to marketing when a firm's data lives in a central lakehouse instead of a stack of disconnected systems?

In this episode, Jason Kennedy, CEO of Choate Frazier, makes the case that modern legal marketing requires a marketer who can speak the language of IT, knowledge management, and innovation. Jason shares his journey from CMO to marketing ops to data strategist at Holland & Knight, and breaks down how Big Law firms are rethinking their MarTech architecture to move past fragmented spreadsheets and second copies of the truth. He argues that you can’t prove marketing value when your team spends all its time putting out data fires. That philosophy shapes everything from how firms evaluate CRM options across the Am Law 200 to why headless CRM is gaining traction.

He explains why lakehouse architecture gives marketing unfettered access to governed firm-wide data, why data silos are giving rise to expensive AI sprawl, and why finding your North Star is key to earning a seat at the table. Jason also gets honest about why measuring ROI is so hard when partners act as the sales force, and how data helps you tell a partner why a prospect is a waste of time.

Timestamps:

(00:00) Intro

(01:51) The struggle to define marketing ROI in professional services

(02:46) Discovering the power of legal data

(04:03) Crash course in data architecture at Holland & Knight

(06:54) What is a data lakehouse architecture?

(08:52) Differences between a data lake, warehouse, and lakehouse

(10:19) Why traditional CRMs become a second copy of the truth

(12:49) The reality of being data-driven in Big Law marketing

(25:36) Evaluating the Am Law 200 CRM landscape

(29:19) Exploring headless CRM options in legal tech

(34:49) Avoiding the hidden trap of AI sprawl across MarTech

(37:16) Practical first steps for data-driven marketing

Connect with our guest:

• Jason Kennedy on LinkedIn: https://www.linkedin.com/in/jmkennedy/
• Learn more about Choate Frazier: https://www.choatefrazier.com/

Connect with Tom:

• Tom Baldwin on LinkedIn: https://www.linkedin.com/in/tombaldwin/
• Learn more about Entegrata: https://www.entegrata.com

What does it actually take to get 70-80% of attorneys using AI every month? In this episode, Tim Fox, Chief Data and AI Officer at Ogletree Deakins, makes the case that adoption isn't a byproduct of a great tool - it's a strategy in itself.

Tim shares his journey from mailman to litigator to C-suite AI strategist, and breaks down how Ogletree Deakins moved past the hype cycle to hit usage numbers most firms only dream about. His thesis: if people aren't using the tool, it wasn't worth building. That philosophy shapes everything from how they evaluate vendors to how they staff their AI program.

He explains why AI requires dedicated people (not just platforms), why early adopters can only carry you so far, and why the buy-vs-build debate misses the real question - which is whether anyone will actually show up to use what you deploy. Tim also gets honest about what attorneys really think about time savings, and why "five hours saved" doesn't land the way technologists expect it to.

Timestamps:

(00:00) Intro

(01:50) Mailman transitioning to legal AI leader

(06:09) Transforming firm data into strategic advantage

(07:45) Settlement data extraction insights

(09:09) Leveraging external data for competitive advantage

(10:32) Four key barriers to AI adoption

(15:31) Training staff for effective AI usage

(18:55) Buy and build AI strategy explained

(21:33) How to run vendor demos successfully

(25:36) Managing legal tech ecosystem sprawl

(36:27) Regulatory data insights for labor law

(39:10) Sequencing data strategy and governance

Connect with our guest:

• Tim Fox on LinkedIn: https://www.linkedin.com/in/tim-fox-legal/
• Learn more about Ogletree Deakins: https://ogletree.com/

Connect with Tom:

• Tom Baldwin on LinkedIn: https://www.linkedin.com/in/tombaldwin/

Learn more about Entegrata: https://www.entegrata.com