#71 Stop with the AI generated cover letters! Hiring Legal Ops in 2025

In this episode, Mary O’Carroll reunites with Anne Kerwin Payne of Kerwin Associates to dig into one of the most misunderstood yet high-stakes roles in legal: in-house legal operations.

If you’re a GC hiring for legal ops—or a candidate trying to land that elusive “head of legal ops” title—this one’s for you. Anne brings decades of legal recruiting insight, a front-row seat to the evolution of the legal ops role, and a refreshingly candid take on what works (and what definitely doesn’t).

In this episode:
What Even Is This Job? Why the role of legal ops is still hard to define—and how that creates hiring gridlock on both sides.
The Strategic Leap: What it really takes to go from #2 legal ops to department lead—and why most people underestimate the soft skills required.
Hiring Mistakes GCs Make: From hiring too junior to skipping overqualified candidates out of fear, Anne shares the missteps she sees most often.
The Resume Trap: How over-engineered CVs, AI-generated cover letters, and fuzzy job histories are derailing great candidates.
Title Chasers vs. Builders: A frank conversation about compensation, career moves, and the difference between a “job” mindset and a long-term career play.
The GC-Legal Ops Chemistry Test: Why your first hire in legal ops needs to be more than a taskmaster—and how to find a true partner.

Whether you're trying to land your first legal ops role, move up the ladder, or finally hire the right partner for your legal team—this episode lays it all out. Mary and Anne cut through the noise with practical guidance and stories that’ll help you make smarter moves in a role that’s only getting more critical.

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DISCLAIMER
This video is for informational purposes only and does not constitute legal advice. If you need personalized legal advice, please contact a licensed attorney.

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