Artificial intelligence is transforming the practice of law in countless ways, as I’ve explored in this podcast and newsletter. Thus far, I’ve focused mainly on AI’s implications for lawyers and law firms. But how is AI affecting clients, what they expect from their firms, and the attorney-client relationship?
Sabastian Niles, the president and chief legal officer of Salesforce, tackled these topics in an open letter he published last month, “How Law Firms Can Lead the Agentic AI Era—And What Clients Now Expect.” After reading his letter, I thought he’d be the perfect guest to help me explore these critical subjects.
We began our conversation by covering Sabastian’s path from mock trial champion to Wachtell Lipton M&A partner to CLO of one of the world’s leading technology companies. We then turned to AI in legal—discussing what “agentic AI” actually means, how Salesforce evaluates outside counsel on AI adoption, and why Sabastian believes that trust and innovation, far from being in tension, go hand in hand.
Thanks to Sabastian for speaking with me—and thanks to him for his invaluable insights into the future of law and the legal profession in the age of agentic AI.
Show Notes:
Sabastian Niles bio, Salesforce
How Law Firms Can Lead the Agentic AI Era—And What Clients Now Expect, by Sabastian Niles for Salesforce
Sponsored by:
NexFirm helps Biglaw attorneys become founding partners. To learn more about how NexFirm can help you launch your firm, call 212-292-1000 or email careerdevelopment@nexfirm.com.
Three quick notes about this transcript. First, it has been cleaned up from the audio in ways that don’t alter substance—e.g., by deleting verbal filler or adding a word here or there to clarify meaning. Second, my interviewee has not reviewed this transcript, and any errors are mine. Third, because of length constraints, this newsletter may be truncated in email; to view the entire post, simply click on “view entire message” in your email app.
David Lat: Welcome to the Original Jurisdiction podcast. I’m your host, David Lat, author of a Substack newsletter about law and the legal profession also named Original Jurisdiction, which you can read and subscribe to at davidlat.substack.com. You’re listening to the ninety-sixth episode of this podcast, recorded on Tuesday, April 14.
Thanks to this podcast’s sponsor, NexFirm. NexFirm helps Biglaw attorneys become founding partners. To learn more about how NexFirm can help you launch your firm, call 212-292-1000 or email careerdevelopment@nexfirm.com. Want to know who the guest will be for the next Original Jurisdiction podcast? Follow NexFirm on LinkedIn for a preview.
As loyal listeners of the OJ podcast are well aware, I’m very interested in how artificial intelligence will transform both the practice of law and the legal profession. Thus far, I’ve discussed AI primarily from the lawyer’s perspective, focusing on subjects such as how attorneys are integrating AI into their practice or how it might affect employment opportunities for lawyers.
But what about AI from the perspective of the client? To tackle that topic, I was delighted to interview Sabastian Niles, president and chief legal officer of Salesforce. As the top lawyer at Salesforce, a Fortune 500 and S&P 500 company, he’s a sophisticated consumer of legal services. And he has definite views on how lawyers and law firms should be using AI—which he outlined in a recent open letter to Biglaw, “How Law Firms Can Lead the Agentic AI Era — And What Clients Now Expect.” After reading his open letter, I knew that I wanted to have Sabastian—who graduated from Harvard Law School and was a partner at Wachtell Lipton, before joining Salesforce—on the show. Without further ado, here’s my conversation with Sabastian Niles.
Sabastian, thank you so much for joining me.
Sabastian Niles: Delighted to be here, David.
DL: And I should thank you for your great work at Salesforce. Disclosure to my listeners: I’ve been a shareholder since 2009, so I appreciate your efforts.
Turning to you, let’s start with your background and upbringing. Where did you grow up?
SN: I was actually born up in Portland, Maine. When my father got stationed at Walter Reed, I grew up in the Maryland, D.C., Virginia area—mostly in Maryland. And then, as you know, we worked together in spirit at Wachtell Lipton Rosen & Katz.
DL: Yes, and we will get to that. But let me ask: did you have any lawyers in the family? It sounds like your father was perhaps in the armed services.
SN: No. We had educators, people in healthcare, folks doing different things across various fields. It’s a strange thing—I hadn’t really thought about it before, but I may be the first lawyer in our family or extended family. Certainly, at the moment, I am the only lawyer.
DL: So why did you go to law school, then?
SN: I had been very involved with our mock trial team back at the University of Maryland, and it was very intense—very much built on pillars of discipline, dedication, and seriousness of purpose. We had a wonderful mentor and coach, Dr. Noel Myricks, and we won a number of national championships. I was really into the Federal Rules of Evidence and the like, and I thought I’d go down that litigation path.
It’s funny—my mother found something recently. I’m sure you did this in high school: those superlatives where it’s “most likely to do this,” “most likely do that.” But also, at the end, the school newspaper would do little write-ups of a whole bunch of seniors. There was this one question: what do you want to be when you grow up? And I was actually stunned, because what I had written was, “I want to be a high-tech corporate lawyer.”
DL: Huh, okay!
SN: It really says that. Now I’d probably say life is not linear, but it’s interesting how things can play out.
DL: You mentioned that you were active in mock trial and were looking at litigation. How did you end up doing corporate or transactional work when you went to Wachtell Lipton after HLS?
SN: There were a couple of different influences. I remember in my second or third year of law school, I had this terrific M&A course from Chancellor Leo Strine, who became a very good friend and mentor. I loved getting deep into the cases and the case law. Even at Wachtell, when I ultimately transitioned from being a litigator, I was one of the corporate lawyers who had really read all the cases, because I found very useful principles in them. I also had a terrific mentor and professor, Guhan Subramanian—I think you know Guhan as well—who’s a professor at Harvard Business School and Harvard Law School. And I remember Lucian Bebchuk—he and I, even after I was at Wachtell, we’d get into our fights on empiricism, and Marty Lipton did all this work too.
But it was really working at Wachtell as a summer associate where I had the opportunity to work across practice groups. I remember it was a July 4th weekend—you may recall that Wachtell wasn’t really a place where you do those three- or four-hour lunches, in fact, my whole summer I think I may have gone out to lunch once—when I had the opportunity to work on this fascinating case—I think it was the NeighborCare/Omnicare, a healthcare hostile, contested takeover situation. That weekend, the hostile turned into an aligned, friendly, agreed-upon deal, and I was very engaged with it.
I was reading the merger agreement, MAE clauses, thinking about how you’d negotiate this, bringing to bear so many different sets of functions: the legal questions, fiduciary duties, but also thinking through this in the context of the business strategy of the investors, employees, PR, and the relationship between the board and the management team, the diligence—and I’m like, “This is the most exciting thing I’ve ever done.” Maybe as life unfolds, you can say, “Okay, this is where you get your dopamine hits.”
To be honest, I also found litigation tremendously stressful, and corporate was much calming. In law school, I had done a lot of work with the Program on Negotiation, Getting to Yes, and so on. And so these pieces ended up coming together a little bit by happenstance, but maybe there’s also a trajectory there.
DL: So by the time you returned to Wachtell full-time, had you already decided to focus on corporate work after that summer?
SN: Yes, I started full-time in corporate. As you know, the corporate department at Wachtell is generalist in the sense that it covers all the different elements of corporate work in a highly cross-functional place. You’re bringing in litigation teams, finance and restructuring teams, exec-comp and employee-benefit teams—all to advance whatever particular corporate objective the client is seeking to achieve.
DL: I feel that Wachtell is one of the few places where lawyers have the luxury of being a little more generalist; there’s been this hyper-specialization at a lot of other law firms. But as you mentioned, the Wachtell corporate department covers a lot of things—you might handle the financing for a deal and the underlying M&A deal, the SEC stuff, or be involved with handling litigation. So when you were there—you started there after HLS, and then you made partner—did you have a practice focus or an industry focus?
SN: In terms of industries, I was always industry-agnostic, but I did end up working a lot in technology and REITs—I love my REITs and real estate. But I’d also work in a lot of the regulated industries—healthcare, life science, financial services—and really the full swath, including industrials and retail. The areas I’d be particularly lead in were basically things clients were either really excited about or really stressed about. That’s why it became very stimulating and interesting.
You also have people you’re mentoring and developing at the firm, and practice groups and teams that you’re leading. The areas were: contested situation, whether driven by some stakeholder pressure—shareholders, employees, others—certainly takeover preparedness or M&A transactions, but also broader corporate governance. It could be enterprise risk. It could be, obviously, sustainability-related areas. Those always spanned industries—working on the spinoffs and different areas. In the corporate life cycle, one of those key moments is also board refreshment or succession. So really across industries, and also across the various corporate moments: the IPO, the merger or combination, operating in the capital markets, being a public company and trying to balance long-termism and short-termism.
A good friend of mine actually said, “Oh wait, is Sabastian the partner of special projects?” Well, we all were at Wachtell, in some sense. Because to your point, Marty Lipton and I were just having lunch the other day—he’s such a good friend and mentor, 94 now and still coming into the office, which I thought, health-permitting, I would still do—and at the end of it, I said, “Marty, you’re not 80 years old anymore.”
DL: To finish up on your career: you were at Wachtell Lipton, a great firm. I know it well having been there also, although not as long as you. And it is, in many ways, arguably the top M&A corporate firm in America. You were a partner there, and we all know Wachtell Lipton partners make a very good living. But you’re coming up now on your third anniversary at Salesforce, having left Wachtell in 2023.
Why would you leave such a storied firm, even if for an admittedly great opportunity? Tell me your thought process there.
SN: It’s been an exhilarating three years, and I’m very excited to see all the things we will continue to do in the years to come here at Salesforce. It relates to what I was saying: yes, Wachtell is quite an institution. But Salesforce offered a unique opportunity to come in as president and chief legal officer of a company whose number-one value is trust. We’ve got five core values here: trust, customer success, innovation, equality, and sustainability. Salesforce has led so many companies in the industry through technology-related transformations. I’d been leading various AI items for a while, and then came GenAI, and then now the agentic-AI phase. The opportunity to continue to have impact, to lead and grow—and I got these incredible global teams at a time of such transformation—it just really continues to be just an incredible and humbling time. It scratches that whole itch I had around AI and technology. And then, again, how do you navigate that from a trusted-advisor lens?
DL: So it sounds like perhaps you were drawn to the breadth of the role compared to your work as a law firm partner. What specifically drew you to Salesforce to pursue that opportunity? Had you worked with Salesforce as a client?
SN: I had the privilege of working with Salesforce as a client on a number of different transactions and governance items—certainly during the period where Salesforce demonstrated it was possible not just to come out on top, but to really control our destiny when we had, I think, about seven activist investors, all with really important points of view. It was a real opportunity for the Salesforce leadership team to define and chart a path forward, taking into account inputs and perspectives from the full set of shareholders and stakeholders, and to drive forward a terrific path ahead.
To your point, this is going to sound kind of crazy, but both Wachtell Lipton and Salesforce have very strong cultures, a very strong set of values, and a very strong commitment to excellence and high performance. So in that sense, there were similarities, but in obviously different contexts—navigating, guiding, and driving forward with my C-suite colleagues, and through all of our 85,000 people here. I’ve also had the opportunity to work with a lot of companies and to spend time with, learn from, and work with tremendous executives across all the clients that I’d worked with—certainly GCs and CLOs, but also CFOs, CEOs, and members of boards of directors.
So what attracted me was this continued growth, curiosity, challenge, and the leadership and development opportunity for talent. How do you really align and develop and make sure we have great managers and great leaders? And so it was a little bit all the above, but definitely being at the center of AI technology and bringing an advisory approach at scale and to our customers has all just been very exciting. And we’re at this moment where you have to ask: how do you architect and deliver AI technology and data in ways that are secure?
DL: So let’s turn to AI and technology. You wrote a great article, which I will put in the show notes, “How Law Firms Can Lead the Agentic AI Era—And What Clients Now Expect.” So before we dive into the substance of the article, because my listeners have varying degrees of proficiency and knowledge of tech, I should ask: what is meant by agentic AI, as opposed to generative AI, as opposed to just pre-gen AI? What is meant by the word agentic? (Am I pronouncing that right?)
SN: You’re doing great, David. Agentic AI grapples with how we take these tools and technologies and evolve from rules to reasoning—navigating standards, planning actions, reasoning around what’s the best path forward, and then actually executing on tasks to drive whatever the enterprise mission is or whatever the humans have directed. And as you can imagine, as you move to more varying levels of autonomy—always with human oversight, strong guardrails, strong explainability, and we can talk more about what that means—you have to ask: what’s the governance observability around these areas?
You can have multiple-agent systems. For us, we run the whole company right on Slack. We have our own agents and other people’s agents, all operating with us on this global platform. And with agents, the question becomes: how do you, in the flow of work, have human teams working with and managing these agents? In companies, it’s the concepts of individual contributors versus people leaders—individual contributors are the people who don’t directly manage other people. I’ve said that in the future—and actually, right now—every individual contributor, David, will have an agentic span of control, because they will be managing AI agents to help augment them, amplify what they’re doing, and automate certain portions of their tasks to get the work done. Even when you think of agents, this is where the different subsets come in—how do you build that overall agentic stack across those systems.
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So you wrote in the open letter that I mentioned, “Firms that don’t integrate best-in-class commercial solutions and AI will find themselves outpaced by leaner, more agile competitors.” So from where you sit as somebody who retains outside counsel, do you have any criteria that relate to a law firm’s use of AI when you are thinking about whether to retain that firm?
SN: I love the question. Let’s just take a step back. This is what prompted me to write this open letter. It arose from a lot of conversations that I’d been having with a broader group of professional service and advisory firm leaders—lawyers sharing with me the challenges they face around technology, data, and certainly AI: uncertainty about how to use it, whether to use it, how to implement it. But also, for some of the people who are more on the cutting edge: how does an advisory firm, a law firm, or a legal professional work with and alongside AI, in ways that can build trust rather than burn client trust? How might you use it to grow the firm?
Of course, some partners are wondering how can they increase their margins. But also: what’s the new relationship that needs to manifest between law firms and advisory firms and their clients? Where and how are the tremendous gains—productivity and otherwise—that will arise from really embracing technology, data and AI? How are those gains going to be delivered and shared with clients and with colleagues within the firm? As I write in the letter, with expanded capacity, how might this also strengthen the profession’s standing with communities? With expanded capacity from AI and tooling, are you going to be able to expand your pro bono impact? On the colleague side—the people operating within these professions—how do these firms become the employer of choice, particularly for AI-native generations?
From the client side: what do clients expect? What are we looking for? Of course, when a firm is leveraging these tools—and we’ll talk about why I think it’s so important for them to do it—we want it all. We want superior service. We want deeper insights. We want faster outputs and better outcomes. And we also want the firms to share with us in the sense of savings, cost efficiencies, and improving business operating models. We want firms to demonstrate that they have the same level of digital maturity as we have at Salesforce.
DL: Just to make this a little more concrete, because a lot of this is very abstract: do you have a particular question that you ask during, say, a beauty contest? Do you have a provision or two in your engagement or retention letter for outside counsel about AI? How are you actually operationalizing seeing how your outside firms use AI and innovate with AI? Or is it just something in the ether? How do you follow up on that, very concretely?
SN: It’s the same as how we operate internally—being customer or client zero of all of our own internal solutions—and how we are embedding often our own AI agents in every single part of our workflows. We get hundreds of thousands of requests a year. And so how are we building? We run the whole company on Slack. We’re the number one user of Slackbot. In Slack, we’re triaging, we’re allocating work, we’re enabling—through our own AI systems that we’ve built—so many routine inquiries able to be addressed directly, while also advancing some of the key work, freeing up our teams and building capacity to focus more on the high-stakes, critical work of judgment and execution that requires a fuller set of approaches.
And look, when it comes to our law firms, we are expecting a couple things. We are entering into our panel selection process, thinking about how the firms go through different sets of areas. We have firms we’ve worked with, and we’re certainly expecting, this coming cycle, that firms will come forward and engage on each of the areas that identified in the open letter—and with some granular elements. There are questions around how are they using technology, data, and AI with respect to their practices. How are they using it to develop their internal teams? How is it informing the service delivery models that they are providing? But also, what are the guardrails that they have been putting in place around these issues?
Trust can be built through these things, but trust is fragile. And I’m sure you’ve probably written about it: there are almost daily reports of judicial sanctions related to misuse of AI. I call it the cardinal and avoidable sin of inventing citations and hallucinating precedent. Why does that occur? It’s because of a lack of rigor, lack of guardrails, lack of human oversight—and perhaps a lack of really understanding and grappling with the technology. So that also becomes part of the conversation.
Do these firms have an executive sponsor responsible for AI governance and agentic workflows? What are their internal guardrails for the trusted use around these items? What are the protocols that they have in place to protect attorney-client privilege and client confidentiality throughout the stack? Are they able to come forward to us and show, “Here’s our current use of these tools and how they’re going to work with us”? We have many law firms we’ve put on Slack; that’s our engagement model with them. But I really want to understand how they’re using this in terms of risk management. Where are they using AI agents and other of tools? Are they using it to automate tasks? Are they using it to scale human judgment? To reduce error, to increase speed, quality, trust?
When you think of litigation contexts, plaintiffs’ firms and potential disputants are using AI to build their cases. So if we’re on the defense side—or sometimes we do offensive litigation—how are firms ensuring that they are maintaining that competitive level, or even that competitive superiority? When AI technology or data reduces time and cost and expands the capacity of teams, is that going to be a growth lever for the firm to be able to provide expanded service offerings? And where and how are those savings going to be shared with clients?
We want to know how are they equipping their associates, counsel, and partners, not just with the legal acumen that the firm should be great at, but also with technical fluency and agentic-workflow competence. And are they transparent with us around where and how they’re using these tools? It’s a series of questions, but I’m looking forward and eager to have firms present a vision—their vision around these items, not just particular point solutions. We want them to co-architect with us what that future of the legal industry looks like, because that’s a broader piece here. There’s certainly us as clients—I talk to my peers and colleagues at other companies. But I think the biggest opportunity is for the legal industry as a whole to really tackle and grapple with the complexities around ethics, risk, and accountability—and really help the whole world tackle this era in a responsible but accelerated way.
I’ve talked about this before, and we discussed it earlier, David: the traditional, conventional wisdom is that you’ve got trust over here and innovation over here, as if they’re in tension with each other. I’ve never believed that. Trust is really a form of velocity. Trust can be propulsive; it is propulsion to innovation. Why? Because trust enables adoption, right?
DL: That’s a great note on which to end our substantive conversation. Our time is running a little short, so I want to move to the speed round. These are four standard questions. They’re the same for all my guests.
My first question is, what do you like the least about the law? And this can either be the practice of law or law as an abstract system.
SN: The practice of law is fulfilling. It’s intellectually demanding. It’s very high-stakes. But there are areas that can feel tedious, and areas where you’re required to bring extraordinary endurance and intensity, which can be incredibly fulfilling and exciting. But when you combine the areas of friction and tedium with remote work plus the level of intensity…. That’s why I’m really bullish about the potential for agentics and AI to tackle both of those areas. One, deal with all the administrative and routine work, to unlock more focus on that high-stakes, high-value, high-judgment work. Two, can you achieve really high performance in ways that prove more sustainable? That’s the thing I tell my whole global teams about AI transformation. What’s the ultimate goal? One ultimate goal: can we make your work more sustainable, more joyful, more productive, more pleasurable—where we’re using these tools to really help each other succeed?
DL: My second question is, what would you be if you were not a lawyer?
SN: There are all the areas that I could go into around AI—strategy, advising, building businesses and processes that are trustworthy and scalable. But you know what? If I weren’t a lawyer, I’d probably be a life coach. A lot of what I do and have done in my life, you can imagine, is navigate people through high-stakes decisions. People are excited about things; they’re stressed about things. So I’d try to be a life coach.
DL: My third question is—and I’ll be very curious because you have a legal hat, an executive hat, and you’re also a parent—how much sleep do you get each night?
SN: Three to 12 hours. For 18 years, my wife was saying, “I think you have sleep apnea.” I finally got it checked, and I have mild sleep apnea. I got this CPAP machine last week, and it has been incredible. She says, “You’re not snoring anymore,” and I sleep like a baby through the night. But definitely sometimes two to three hours. Or last Saturday, I said, “I’m taking a nap,” and I went to bed at around 6:15 p.m., and I woke up at 6:30 a.m. So that’s why I don’t know what the mean, median, or mode is of my sleep, because it definitely varies.
DL: Fair enough. And my last question is, any final words of wisdom, such as career advice or life advice, for my listeners?
SN: I try not to give advice.
DL: You’re a life coach!
SN: As a life coach, you help people reach their own conclusions, help companies and CEOs and directors reach their own views. The main thing is to really embrace that each and every one of us is a steward. We’re stewards of trust. We’re stewards of whatever it may be. We deeply care about capital, but when we think of being stewards of trust in this area of technology, we should all be working to use agentic AI so you can focus on what we value the most: high-impact, high-stakes, creative work that you feel brings out the best of humans and AI working together.
When we think of AI, you need to really grapple with the complexities—trust, risk, accountability—but embrace how it can extend your reach. It can let you focus on what your people and your teams can do. How do you lead with integrity around it, building that trust, solve high-stakes items? And also figure out how to get the best ideas, assessment, views around whatever technology or product you’re trying to deliver, for an enterprise or for yourself—that notion of humans and agents teaming together. In all these areas, we’re in such a novel moment, where you can blend that beginner’s mind with your expertise and just go: have impact, find your purpose, and hopefully lead an incredible, meaningful life.
DL: Well, I do think you’ve had a very meaningful life and career, and you’ve given a great amount of thought to some very complex questions. I appreciate your insight. Sabastian, thank you so much for joining me.
SN: Thank you, David. I was delighted to be here.
DL: Thanks so much to Sabastian for joining me, and thanks for his insights into such a timely topic.
Thanks to NexFirm for sponsoring the Original Jurisdiction podcast. NexFirm has helped many attorneys to leave Biglaw and launch firms of their own. To explore this opportunity, please contact NexFirm at 212-292-1000 or email careerdevelopment@nexfirm.com to learn more.
Thanks to Tommy Harron, my sound engineer here at Original Jurisdiction, and thanks to you, my listeners and readers. To connect with me, please email me at davidlat@substack.com, or find me on Twitter, Facebook, and LinkedIn, at davidlat, and on Instagram and Threads at davidbenjaminlat.
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The next episode should appear on or about Wednesday, May 13. Until then, may your thinking be original and your jurisdiction free of defects.
