CKIO Fisher Phillips | How a Law Firm Wins Business with Custom AI

Most engineering leaders know the build vs. buy vs. partner question. Evan Shenkman is living the answer, and it's all three at once. Evan leads knowledge management and innovation at Fisher Phillips, a large labor and employment law firm that's quietly become one of the most aggressive AI adopters in legal.

The playbook is set in legal, but it travels.

*In this conversation, Josh and Evan cover:*
- Why build/buy/partner stopped being a choice and became a portfolio
- How to hire across the AI-ML and domain-expert seam (and which soft skills actually matter)
- The "moneyball" approach: turning years of messy, unstructured expert data into a working tool
- Why the model du jour problem is a feature, not a bug
- How attorney-client privilege becomes a real competitive moat when you build your own tools
- What Evan's path from practicing attorney to AI team lead says about non-linear careers in tech leadership

*About Our Guest*
Evan Shenkman leads the knowledge management and innovation function at Fisher Phillips, a large labor and employment law firm. After ten years as a practicing attorney, he moved into KM, then data analytics, then AI, becoming one of the earliest adopters of generative AI in the legal industry. His firm was a design partner on CoCounsel, the first GenAI tool built for legal work, and now runs an in-house team of ML engineers and former practicing lawyers building custom AI tools on top of foundation models. Evan isn't a coder. His job is making sure the people who are can work seamlessly with the people who practice law.

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