Ken, Jessica, and Jenny Hamilton, CLO of Exterro, discuss AI’s potential in the legal profession. They dive into their favorite tools and how to apply them, as well as the importance of human oversight to ensure accuracy and compliance. Jenny also shares strategies for driving adoption within her team and making sure new tech meets the needs of her team.

Tune in to hear personal experiences, practical insights, and expert opinions on AI’s transformative potential and its challenges in legal.

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02:20 - About Ken

03:49 - About Jenny and Exterro

05:05 - What’s exciting, what’s scary about AI?

09:28 - Helpful tools

17:58 - Driving adoption

23:23 - How to be a new adopter

26:18 - Advice for entry level associates

37:39 - How AI disrupts the law firm model

46:25 - Keep or redline

49:46 - Final takeaways

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Sandy MacDonnell, Head of Legal Ops at DocuSign, and Krysta Johnson, Senior Legal Ops Evangelist at DocuSign, highlight the importance of metrics, data, and AI in transforming the legal profession from cost center to strategic, growth-oriented role. Sandy and Krysta both stress the need for adaptability at a time of rapid tech changes, as well as best practices for implementing new legal technologies.

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SANDY:  I think this is true about the rest of the industry as well, is that, you know, it's really seeing legal and putting legal in that more strategic kind of role and being that partner to the business, and being that department of yes and like, how does the legal team help our sales team sell more, not just tell them how they can't do things. So I think that's been a really fun evolution of, of the legal operations function. Um, and I'm just excited because I think it's opening up a lot of career opportunities for folks who've been in these types of roles. It's much more creative, much more kind of fun and, like forward looking, I guess I would say.

SANDY:  I think if there's anything I've learned in legal operations, it's like things change all the time, right? You had like one thing you were running towards and the next day the GCs like, Hey, actually I wanna go chase this other thing. Being flexible, being, uh, adaptable, continuously learning, right?

Like in this world today that we're living in with ai, we're seeing, you know, like the legal landscape always changed quickly when I think about technology. But today it's changing so much more rapidly. So if you have some, you know, if you're hiring someone to do legal operations for you, that person better be super excited about change, about, you know, learning the new technologies, what's coming down the line, how are we gonna reshape our department to, to adopt those new technologies. Just so essential.

KRYSTA:   We operate currently in most of the corporate world, in these very, somewhat isolated silos. Yes, there's some cross-functional collaboration, but I think the idea of these silos is what really kind of stifles a lot of change that could move a lot faster.

And I think we're going to see more centralized operations functions where there might be a, like dedicated people that support legal operations, but they will sit in a more dedicated operations function under say, the COO versus sitting within the legal team. As you said, Sandy, like there is a lot of democratizing of technology and like ability to educate yourself.

And I think just like we've seen changes in the past 20 years in the legal, like the legal field itself, we, we'll see that change in operations as well where you, you don't have people doing a lot of the more menial work.

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Todd Smithline, CEO of Bonterms, describes the importance of developing skills that go beyond your legal expertise. Salesmanship, project management, and information synthesis all lend themselves to adaptability in both legal and non-legal roles. He describes the value of feedback, how to offer value to your clients, and how to stay positive.

Bonterms is the two-sided negotiation platform built on Standard Agreements. We solve contracts for Procurement and Sales, while keeping Legal happy. Average negotiation times on the Bonterms Platform are measured in minutes. Bonterms is lawyer-led and funded by XYZ Capital and Wilson Sonsini.

“ So I learned how to create a brand, how to create a product. Because even as lawyers, we are selling a product. I learned how to price a product, how to market a product, how to get a customer. How do you get a recurring customer? … I made the full step, the crazy step, the completely off the pier and into the bay step of stopping being a lawyer altogether. But even after that last leap, I took all my friends with me. I created this committee of 100 lawyers. I had a relationship with my prior firm. I was able to leverage the next step.”

“The one piece of advice I think I'd give lawyers who are interested in doing this: Sometimes I see this thing on LinkedIn where people say "Recovering lawyer" or "Former lawyer" or something like that. And I think I read that differently maybe than it's intended because I read it as them distancing themselves from that expertise and that experience. Whereas I think one of the easiest ways to make this move as a lawyer is to build on it, right? I think that all three of us did that, right? We didn't desert our former expertise, our relationships. We used them to spring to the next thing.”

“ I think the highest prized skill right now, across companies, is the people who can synthesize disparate information. And communicate it well, but at the same time deal with complex situations and nuance. This is something a lot of lawyers are trained to do. One of the skills that we really develop with lawyers is concentration. Paying attention to the details, pulling together disparate facts, and synthesizing information. So I think that is really going to be the coin of the realm going forward.”

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01:12 - Meet David Wang

03:27 - Meet Todd Smithline

10:25 - Taking the leap away from legal

18:02 - Ensuring success in any role

27:47 - Non-legal roles to pursue

34:29 - How to approach law school

54:32 - Defining your value

55:52 - Keep or redline

57:45 - Where to find Todd

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