Tech Teams Today · 2026-05-28 · 41 min
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.
Sr Dir @ OpenGov | How To Cut AI Signal From Noise56 / 100
Dir of Eng @ Mosaic | Over 90% of Their Code Is AI-Generated
Sr Dir @ Twilio | AI, Judgment, and Engineering at Massive Scale
CTO Cube | Coding Got Easier. Engineering Didn't.
AVP GM Financial | Why This Engineering Leader Isn't Worried About AI