I’ve Been on LinkedIn for a Long Time

I've been on LinkedIn for a long time and rarely posted. That’s probably going to change.

For context: I’m Chief Legal Officer and head of HR and other departments at Cennox, operating across the US, UK, and EU. The role sits at the intersection of legal, HR, compliance, and operations, which in practice means dealing with problems that don’t belong neatly to any one function.

Before this, I spent a couple decades across legal roles (ADA, General Counsel, litigation, municipal, corporate), plus teaching IP, Corporate and Cybersecurity law as an adjunct professor at Seton Hall. Useful background, but most of what matters now looks very different from how any of that was originally taught.

Lately, a good deal of my time is spent analyzing and implementing AI and other technology solutions inside legal and HR workflows.

Not just evaluating it. Not just talking about it at a high level. Investigating, building, and deploying it in environments where the margin for error is low and the accountability doesn’t go away just because a model was involved.

The interesting problems aren’t the ones you see in headlines. They’re much more operational:

• Who is accountable for an AI-assisted decision?
• How do you make outputs explainable enough to rely on?
• Where do you add controls including confidentiality and security without breaking usefulness?
• What does “good” even look like when the system isn’t deterministic?

Legal and HR teams are being asked to adopt these tools while also owning the risk they introduce. That tension isn’t theoretical, it shows up immediately when you try to put anything into production.

I don’t have clean answers. I’m not sure anyone does yet.

But working through this, finding what actually works, what fails, and what doesn’t translate from theory to practice, seems more useful than another overly polished take on “AI transformation.”

I’m also currently working through a second LL.M. at LSE, which has been a helpful forcing function to think more systematically about some of this.

I’ll share observations here as I can. Mostly where law, HR, and operations collide, and what it looks like to make decisions in that space with imperfect information.

If you’re dealing with similar problems, I’d be interested in comparing notes.