How Top Legal Teams Use AI – Jasmine Singh, Ironclad

0:00But I can also see a world where I see agents going back 45 terms and me just jumping in and being like, pick up the call, be like, hey, our agents are going nuts. We can close this deal right now. We do not need to wait for them to find this out. Why don't we just close it?

0:15Shamil Malachiyev: My guest today is the general counsel at Ironclad. Most people in legal either build these tools or buy them. And she does both. She helped shape one of the world's biggest AI contracting platforms. And then she lives on it too, using it for her own company's contracts. The builder and her own toughest customer. So please welcome Jasmine Singh. And now suddenly the process of intake to Redline is a minute when it used to be potentially days, right? I make two things true. One is I do require usage of AI so they know it is an expectation of mine. it is clear that trying is required. And then I say that failure is acceptable.

0:59So we cannot entirely outsource our profession to agents and say, oh, you know, I don't need to look at this anymore. So at minimum, what I continue to really emphasize is that lawyers who are able to exercise their great judgment, their curiosity, their experience in reviewing AI output are really going to continue to rise to the top. One thing I really don't want to get underemphasized is there is no such thing as right legal advice in the abstract when it comes to business. It is the best legal advice for the circumstance. There's no way it can really understand the human emotion that's involved in closing that deal.

1:39We are the deployers of it for now. I think it can make the feeling of practicing law less isolating, less lonely. And so I'm really excited about what AI can do for us as lawyers. And I think we're still early in the innings. When I first did it, I thought I had ruined my professional career.

1:57Shamil Malachiyev: Hello, everyone, and welcome to this week's episode of The AI Floor. My guest today is the general counsel at Ironclad. Most people in legal either build these tools or buy them. And she does both. She helps shape one of the world's biggest AI contracting platforms. And then she lives on it too, using it for her own company's contract. the builder and her own toughest customer. In the past, she also burned out of big law, walked away to teach 6am spin classes for a year and came back to rebuild all the way to general counsel. So please welcome Jasmine Singh. Thank you so much for having me. I'm thrilled to be here.

2:35Shamil Malachiyev: Thrilled to have you here. Can we start with you telling our listeners a bit about who Jasmine is and what kind of path has she walked to get to where she is right now? Yeah. Yeah. So, you know, I actually love answering that question because I feel like I have lived a thousand lives as a lawyer. I currently sit as general counsel, but I started my career at a very different place. I was a litigator in big law firms in San Francisco for a number of years. As you said, I found myself burnt out and really wanting something different in my career, but really unsure, A, what that was and how to find it.

3:13So I took a break and I became a spin instructor and I'm sure we'll talk more about that shortly. But what that helped me realize was that I wanted to come back to the law in a way that allowed me to really connect and continue to find my joy, my passions in life by way of mission-driven companies and helping to build things. So I transitioned in-house first to 24-hour fitness, which was a really nice connection to my personal passion around fitness, health, and wellness. Cut my teeth as a commercial lawyer there and then moved on to Pinterest where I led global commercial and scaled my team. And then moved on to being DGC at Patreon, which is a community, a creator-based payments platform.

4:00And then took my first job as general counsel at Binti, which is an early stage SaaS company that makes software for child welfare agencies. and then moved over to Ironclad just a few years ago. And throughout that all, I have remained really active in my volunteer efforts. I'm on the board of a community foundation called Change Lawyers. I'm also on the board of a nonprofit law firm called Public Advocates. I started a decentralized philanthropy initiative called Densert, whereby we raise money for nonprofits that provide direct services. And since you asked who I am, not just what I do, I also am a former competitive bugger and hip hop dancer, which has played a really formative role in my life.

4:44Shamil Malachiyev: So how competitive are you as a person? I'm pretty competitive and mostly with myself. So actually, I have to save it off sometimes because it can be a little unhealthy. but I guess at one point it does help you to like burn out quickly in the situations where you don't find the meaning for yourself but at the same time it helps you scale fast learn quick totally right push right um I grew up playing team sports I also you know I ran track I played basketball I was captain of my respective team so I I take a lot of the lessons I learned as an athlete growing up as a dancer, part of a dance team to my work.

5:28And some of those lessons are around the value of discipline, hard work, never giving up, moving at a fast pace. Also the realization though, that like, I really do go a thousand percent. And in those sports, I knew I needed to dial it back. And the same is true in dance as well. It's if you go full out all the time, it isn't good for your end result, actually.

5:51Shamil Malachiyev: And it's interesting when you compare it to sports, I kind of feel like the last three years, in all of the industries, we're seeing this kind of sprint where everybody has to become an athlete, and just, you know, run as fast as they can. What has that journey been like for you, you know, having to go through so many shifts within industries? Yes. I mean, honestly, it's been a lot of knowing when to push and knowing when to pull back, which is really hard to do to your point when an industry is running at a really fast pace. And starting out in law firms, I think what we're taught is you work to the client's demands.

6:29There is no moment where you actively pull back or say no or limit your work out of self-preservation or whatever else it might mean, because the expectation is if the client is going or if there's a matter that's going to litigation, I was a litigator, you it's full out a hundred percent of your effort. Your time is spent on working and, you know, executing your path. And I think that when I moved in house was the first time I had really heard of people saying like, no balance is okay. Actually, you don't have to give everything a hundred percent. And the expectation is not perfection. The expectation is what the business needs to get the job done.

7:08And so really finding a way to adjust how I was working to my circumstances and the dynamics, I think is the lesson learned. And now to, you know, to address your question around the pace of the industry is changing so fast and it's demanding that we run at a really quick clip. and also that we don't get left behind, right? And so I think that even within this, there is balance to be had, right? It is not, don't adopt the technology. It is absolutely adopt it, learn it, run alongside it, but be really mindful of when and if you need to take moments to breathe and having the agency to be able to do that yourself because nobody else is going to tell you if it's okay or when it's okay.

7:51That has to be you.

7:52Shamil Malachiyev: And I really like that currently, like, yes, you have big law experience. like working for law firms, you have in-house legal team experience. And you're also, I could say, part product manager, you know, using the software, directing the software that actually all of these people use across the industries. It's going to work through their own contracts. Yeah. How is he, what is moving the fastest and how is everyone trying to keep up with the changes? I think what's moving the fastest is, frankly, just the pace of technology development and shift in how quickly models are being developed and then how quickly products are being built on top of those models.

8:37And then how quickly those products are iterating, shifting and delivering new and different use cases. So I think there is just with the advent of AI and the ability to code using AI, there is just way more out there to consume than ever before. And the good thing is, is AI helps you synthesize, shorten and consume it just a little bit more easily. I think the challenge, though, is knowing where to direct your focus at any given moment and not feeling like, oh, my gosh, I just need to look at that thing. And then that one and then that one and not really dive deep into anything. I think that's the the dangerous part of this circumstance is not really giving anything true focus.

9:18Shamil Malachiyev: And not long ago, I released an episode with Xavier, who's also a general counsel at a company called One and Ones. And the thing that he was pointing a lot to is how the dynamic of the interaction between the in-house teams and the outside counsel kind of firms is changing as well. because if we look at the legal firms, they are very consultants-see heavy, right? How do you see that relationship evolving with time? Because I believe that, you know, the six-minute increments and all of that, that is kind of like on the path of disappearing and evolving into something else. Yeah, look, I am of the mindset that each player in the legal ecosystem will continue to have a space.

10:09They just will modify how they approach and occupy that space. So what I mean by that for outside counsel in particular is outside counsel brings multiple things. One is an understanding of a market view, a pan market view, how others are doing it, how peers in the industry are doing it, how peers in other industries are doing it. And sometimes that input is useful for me and there's no way I could get it but for going to outside counsel, right? That value of a firm that knows what a lot of people are doing doesn't go away, in my opinion. The second thing I go to outside counsel for is specialization, expertise in areas where people on my team or me, for example, just don't have a view or a solid understanding of what the law is.

10:54That expertise also doesn't go away. Those firm lawyers have spent years cultivating that understanding, that deep knowledge and skill set. And again, I don't see myself going to them or not going to them for those kinds of deep specialized questions. What I see changing though, is my ability to frame my question in a different way and perhaps go in with a lot more understanding than I would have before. So if before I didn't know a lot about a topic, you know, I obviously, like most lawyers, we do Google searches to try to figure things out and we don't know the answers. And we get enough information to try to frame a better, more pointed question in our heads.

11:36AI has really supercharged that ability, right? Now I can do a ton more research to the point I was making before, I can synthesize way more information. I can question myself. Sometimes what I'll even say is these are the facts and circumstances I'm presented with. What questions should I ask my internal business partners to better understand based on what I believe the legal risk is? Then I go ask those questions and I get the answers. And then I say, now I need a synthesized view of what the outstanding questions are. Then I can go to outside counsel and say, hey, I have this problem. I've done some initial research that suggested to me that like this is relevant information that I want to present you.

12:16Now, can you give me a more time boxed answer to that question based on this investigation? And I have heard outside counsel suggest that this can go two different ways. On the one hand, I think it helps them to...

12:31Shamil Malachiyev: Sorry, I was gonna ask. So do you think that it will evolve to kind of... Somebody has to take responsibility, right, for the final kind of advice and how credible and real it is. So we can do a lot of research, but then what we need the consultancy help for is to say, okay, this is correct. And we put our stamp on making sure that we take responsibility that whatever research you've done is the correct one. correct there is a reason why we go to outside counsel on certain high risks high stakes things right we want people who are experts and who are willing and able to put their stamp and seal of approval on the information and advice they're giving us because they have the lived experience of having enforced it or having seen it in action in other companies and so that accountability is by way of their lived experience really telling us that whatever it is that we're getting by way of advice is helpful or their extreme diligence in looking into the issue, which also is frankly, just something that a lot of in-house teams don't have as much bandwidth to do.

13:39We are more leanly staffed. We have a lot more on our plates than the ability to maybe do a deep dive into some nuanced regulatory scheme, for example.

13:49Shamil Malachiyev: And if we look at like internal legal ops teams, and basically these are kind of like the primary customers of yours in all of the other companies, How do you see their work? What are the biggest parts that evolved with AI? And what are the requirements that's changed for the people working in this? I mean, first and foremost for legal ops teams, I think what's changed is they have to have a deep understanding of what the AI tools are that are out there, how they work, and which ones are right for their team's workflows. And so what I mean by that is like the click-in is you have to understand what workflows your legal team is working on, which of them are automated, which of them are semi-automated, which are entirely manual.

14:35And then if there are tools now that exist that could help eliminate some of the thrash or inefficiencies in any of those systems, and then thinking not just about the system to be built, but the end goal of building that system, I see that as within the purview of legal ops. And it's really just changed the game because now they're not just helping administer what existed before. It's they're doing first principles thinking about how can I reimagine the entire way we've been delivering this legal service. And I think the best legal ops people have already thought that, but now there is new technology at their fingertips, constantly asking for their attention and their evaluation of whether it can actually do that.

15:18So I think that's one part of what's changing for legal ops folks. The other part of what's changing is just their own ability to synthesize reports, information from within their teams. So, you know, to be able to run an analysis of all the tickets that you've ever received and highlight, like, these are the top five themes across the tickets. This is how many days it took us to respond to them. I built an agent to deflect all of those questions such that we never receive them manually in a Slack channel ever again. Like we've got a bot that answers those questions on our behalf. Like that's, I think, the type of work that ops professionals have always been doing, but now we're doing it in a totally different way because they're able to synthesize and digest that information more easily.

16:04Shamil Malachiyev: oh my it's just for for somebody to be a like legal professional right now you have to what now be a you have to understand business processes and be able to map them out and try to automate them um and you have to understand the technology of what ai is where does it fit so is this kind of becoming like a standard pack of like without this like you shouldn't be trying to enter the industry right now you you have to really understand these things? Yes. I do believe, especially to be a successful in-house lawyer, you can't just be someone who delivers good legal advice. You have to be someone who understands, to your point, the business operations and the systems and builds a process to deliver legal advice within that broader system, whatever that might be.

16:57You have to have an understanding of which technology you can use to be able to bridge those two things together and deliver fantastic legal experiences, fantastic legal advice to your clients by way of a mechanism that actually lands for the client.

17:15Shamil Malachiyev: And do you ever feel like, because you have to think on the very kind of like cutting edge of the, because you're busy shaping a product. And right now, everyone has expectations of making their products AI first. And always thinking about, okay, what are the latest cutting edge technologies been released? How do we use that for our product now? How does this change things? And we sort of tend to like as technologists, and I think both of us are, we kind of start living in that kind of bubble where we think, okay, everybody operates at the same kind of level. Everybody listens to the same news.

17:51Shamil Malachiyev: but then when you start talking to people in the industry, you're like, wait a minute. Like, why isn't everyone aware of all of these things? So when talking to the customers, the people out there in the industry, what is the standard adoption level to like compare to your expectation of what it is? Like, what are you noticing? Yeah, I'm noticing three groups of people. There are, to your point, the group of people that are in my echo chamber that are super users of AI. They use it all day, every day. They know what the technology does. They know its limits. They know its benefits. They're constantly tinkering.

18:30And then there's a second group of people who are more in the camp of, I'm being told I have to use AI. I don't really want to. I don't really understand. I'm not the best at this, but I have to. So I'm going to try to keep up. And then there are the people that are, I don't really trust the technology. I don't really see value. It's faster for me. It's better for me if I do it myself. They're the reluctant group, I think, among the three. And right now, I think I see people that are mostly in that middle bucket if I go outside of my bubble. My bubble is mostly that first bucket of like everybody's using it and pushing it.

19:09But I'd say most practicing lawyers that I talk to outside of Silicon Valley, for example, are in that middle area of like, I know I have to use this. and I'm trying my best, but I haven't quite figured it out yet. And if I'm being honest, I'm a little overwhelmed by what I don't know.

19:25Shamil Malachiyev: And what would you say to all of those people? Because clearly everybody is walking this path right now, whether you want to, whether you don't want to. Some of us have already created those neural connections in our brains that kind of help us make sense of these kinds of technologies. What would be the path that you would advise for somebody, for example, on your team who joins is like, I want to learn about these things. was the first step that I took. Yeah, try, try, try, test, test, test. And so to your point, your question about how do I do it on my team, I make two things true. One is I do require usage of AI so they know it is an expectation of mine.

20:03It is clear that trying is required. And then I say that failure is acceptable, right? Like I acknowledge that not everything is going to be perfect, that there are limitations. and I like to have everybody share the stories of when it worked and when it went well and to share those prompts with other people, share those use cases. But we also tell the cautionary stories of here's where it failed and here's where you have to have the limitations in mind and know what to do to overcome those limitations and to create that safe space. Because I think without that, there could be a fear of like, oh my gosh, I don't know how to use this.

20:41And if I do it wrong, what if I make a mistake and then that's worse than where I started?

20:45Shamil Malachiyev: what do you think about yeah speaking to a lot of people most of them are scared because you know they're reading about layoffs and everything and they're like if i if i do my my work too well and that's what like a lot of people who are like on the cutting edge of air they're like well if i automate everything i'm like what am i left to do you know i'm just controlling the system that runs by itself. Yeah. How do we go about actually making sure that people see AI as a friend, as a tool that they can use, instead of, you know, all of this marketing that large companies are throwing out there of like AI replacing everyone, you know, AI first companies are just one person and, you know, all of these agents.

21:29Yeah. So I'm going to start with, I think, what's nuanced in the legal profession in particular is that we have ethical obligations with respect to how we can and should practice law. One of those is the duty of competence, which requires in California that we review the output of AI generated content. Two is a supervisory duty, which is that we actually have to monitor individuals or agents that are creating work product on our behalf. So we cannot entirely outsource our profession to agents and say, oh, I don't need to look at this anymore. So at minimum, what I continue to really emphasize is that lawyers who are able to exercise their great judgment, their curiosity, their experience in reviewing AI output are really going to continue to rise to the top.

22:17I don't see a world in which those lawyers ever don't have jobs because they have to evaluate whether the output is in fact accurate, is in fact correct for the circumstances, is right for the deal at hand, for example. And they also are the ones, to your very good point, that are building and monitoring the systems. Like someone has to say, okay, for marketing content, there is going to be an agent and that agent has to review the output against this set of laws. And when the law changes, but the model doesn't get updated, somebody has to manually upload those new laws or regulations that might apply or whatever changes to the product might have happened to that AI agent's review patterns, right?

23:04Without a person monitoring the system, there is no way it can keep up with the pace of the time. So I think that those two things really still continue to be true. And then even then, the one thing I really don't want to get underemphasized is there is no such thing as right legal advice in the abstract when it comes to business. It is the best legal advice for the circumstance. And only individuals can know the full circumstance of, you know, we got to get a deal done by tomorrow. The counterparty already rejected X, Y, Z. I know that a lawyer on the other side is sensitive to this argument.

23:43So here's how I'm going to position my latest red line to make sure that we get to an agreement today. That's really hard to outsource to AI because there's no way it can really understand the human emotion that's involved in closing that deal. Wow.

23:55Shamil Malachiyev: And interesting that you've mentioned the human emotion too. It's like thinking of, you know, the days back and watching Suits, for example, it really emphasizes the role of relationships, like it's who you know, how do you build relationship, because business is like still between people, you know, there is companies are made of, of people. And do you see that kind of like relationship element ever being replaced by more deterministic kind of rules? Or do you think that is still important? Yeah, I think relationships will become more important than ever, actually, in the age of AI. And that's because the human touch required to deliver the best output still matters, right?

24:41Like, why does software exist? Why does technology exist? To aid humans in doing whatever it is that they want to do with their agency, right? and to outsource certain things to technology, whether it's software, AI, or whatever it might be, it is still in the name of helping, like we are the deployers of it for now. We are the deployers of it. And it is intended to be a tool that we wield and use. And that tool is well wielded by us wanting to achieve certain objectives, do certain things. And so I just, I see that human emotion, human relationships continue to drive it because it's the source of the motivation.

25:25It's the reason why those things exist. And I just don't see that going away. I think the secondary component is really that the relationships help people find and understand what their why and what the impact is a little bit more deeply, right? It's people all want to feel like what they do matters. And if you divorce emotion or relationships from your work altogether, it's hard to find and derive meaning from that work. And that's not to say we won't one day have a world where agents are negotiating with agents to come to terms on contracts. Like I can see a world where that is happening, but I can also see a world where I see agents going back 45 turns and me just jumping in and being like, pick up the call and be like, hey, our agents are going nuts.

26:13Like we can close this deal right now. We do not need to wait for them to find this out. Like why don't we just close it? Right. Because I'm motivated to close it to get it done.

26:21Shamil Malachiyev: Interesting. And one of the questions in this perspective, like if we imagine the future with agents and I'm in software, so it's kind of similar to what's like being changed within legal. How do you see, like, how do people get into the industry? Like, right, when, of course, if you're in top positions and you're kind of driving the changes, it's all fairly easy to you because you have all of those experiences behind you. What about the juniors? You know, people who are just passing their bars, graduating of universities, what do they do? Like, what is going on with, like, junior positions? And what would you advise for people who are thinking, like, oh, I just need an education, I need my diploma and my future settled?

27:00Shamil Malachiyev: How do you see their roles kind of evolving within companies? Yeah, I see their roles evolving specifically in a way that leverages that experience, judgment, curiosity that I just talked about. By that, I mean, those people have to bring those things to bear to do their jobs better, to be able to build the systems, to be able to wield the technology, to deliver legal advice by way of a process mechanism that's better for the circumstance. if all they're doing is, you know, if, for example, what they were doing as a junior associate was redlining contracts, and now perhaps technology is doing that on their behalf, they have to bring the judgment to be able to review those AI outputs and say, actually, that redline doesn't make sense here, or it doesn't apply very well here, or actually, I need to fix my playbook because my position is not what keeps getting redlined into that agreement.

27:54I've got to fix it, right? I've got to tell the AI what to do. So that having that ability to understand what's wrong in a contract and why it needs to be better is the game changer. And if you have the working experience to know what a good red line is versus a bad one, if you have the lived experience of having worked in a business to know like, oh my gosh, the counterparty would never go for that term. That's non-standard. We should not propose it. Those things matter now, I think more than ever before. And so I tell juniors, especially, bring those experiences to bear. They are relevant and they're going to set you apart.

28:29Shamil Malachiyev: And that actually made me think of two things. Like, first one, whenever I hear like, oh, there are huge layoffs because of AI. And then, you know, coming to this topic, I'm like, well, I keep hearing that, you know, lawyers are replaced by lawyers who really know AI, business process automation, a bit of technology as well. and it looks like all of the people who are you know the juniors they are a lot more connected to the technologies you know like back in the day like we we had i don't know when iphones came out and i don't know we started using people who were like 10 20 years older it was harder for them to kind of adopt the technologies like when you're kind of growing up with all of those things and tech it's kind of easier for you to implement that so maybe that will be the big shift like people who don't want to touch AI might find themselves doing something else.

29:23Shamil Malachiyev: Whilst you have all these juniors with all those technical skills that are required for the work coming in. And then the second one is, okay, we have AI. Right now with redlining, like four years ago, you had one contract, you have two days to redline it, go through it, analyze it, understand the context study. Now everyone's like, well, it now takes three hours. So we expected to do two contracts a day or like three contracts a day. So the amount of information that you have to keep in your head, the amount of decisions that you have to make is like three, four, five times as much as it used to be before.

30:07Shamil Malachiyev: How do you stay away from, you know, burning out with this much load, you know, in terms of mental capacity that you need to hold? Yes. I mean, this is actually a great place for AI to take on some of that mental capacity on your behalf. So using AI as a chief of staff, as a work tracking system so that it can help organize your inbox, organize your slacks, keep track of what work you have pending, what work you don't have pending, I think is a vital way to survive in this world. Like if you're not using AI for anything else, at least using it to organize the massive amounts of work that you have to do, I think is essential.

30:51The second thing I'll offer, and obviously this is because I work at Ironclad, it is because of platforms like Ironclad that allow you to log into your dashboard and see what are all the contracts that are pending. What's the status of those contracts? Go into the audit field or the audit trail and say, what's the last activity that happened on this contract? Just having a place to go and say, okay, I don't have to remember every single one of these myself. I can go back to the system and know who was involved, when, what happened, what the ultimate document was, what change I made between version two and six, right?

31:24If we didn't have platforms like that, I think it would be impossible to keep all of what is required of us in our minds at all times.

31:31Shamil Malachiyev: And can we talk a bit about Iron Cloud? I think most of the viewers and listeners would have heard about Iron Cloud. But can you talk a bit about like, what was the platform like three years ago? Right? When the news came out, what did you try as a company? What did they try to implement to change? How did they see the platform evolving? And after you've joined, what are the specific changes that you've seen that, for example, you like the most and you see the most value being created? And maybe we can also touch some of the vision as well. Yes. Yeah. So I'd say three years ago, the platform was, it's, you know, this amazing, beautiful end-to-end tool to facilitate the acceleration of contracts at every level.

32:17So it's not just intake more easily and quickly, but it's also legal review, execution, storing in a repository and getting insights. I think the last three years, the super charge that's happened is how do we optimize each one of those steps to make those things better, faster, cheaper, whatever it might be. And we started with the negotiation front with our Juris tool. And so in the last few years, we've really been working on how do we support commercial lawyers in all of the tasks that they have to do around contracts, whether that's risk review for triage and understanding of what obligations are in an agreement, summaries of agreements, plain English translations of agreements, you know, comparing versions of contracts.

32:59like jurists does all of this. And I'd say in the last few years, we've really tried to give lawyers at their fingertips access to more features, more products that allow them to do their work just a little bit more quickly and easily. And I think the second part of your question is, actually, I'm going to need you to remind me what part two was.

33:19Shamil Malachiyev: I'm sorry. What were the technologies? Well, once you're evaluating, okay, we have these kinds of things that AI can do now. How do we know which ones to use? Yes. Because there's just so many things that you can do. Yes. Okay, great. Yeah. So to your second question about how to decide what AI use cases to optimize and offer to our users, we really thought about the friction points. And so we've deployed agents in those various friction points or we're in the works of deploying some of those agents. So one of those is AI Assistant, which lives next to your, you know, Iron Cloud instance at any time.

33:56So you can type in find me contracts that have XYZ condition true or find me contract with XYZ counterparty, right? So having an ability to natural language prompt your repository or your system to give you results faster, easier, better. But also deploying an agent at the front end to help intake contracts, right? If you think about it for history, when you have a contract review, you go into a workflow, you have had to manually fill out all of the questions that get asked. and then you attach the contract and then you submit it for review. Now with things like intake agent, you can just upload the contract and all of those questions are answered on your behalf.

34:34And all you're doing is validating whether they're true or false and then it gets submitted. And then a tool like jurist will be able to auto-apply a playbook based on conditions that are true in the intake form, propose red lines to an attorney for review, ping when they're ready. And now suddenly the process of intake to red line is a minute when it used to be potentially days, right? And then a contract gets reviewed, negotiated, executed. And what we also know is true about contracts is where you started with the contract and the intake form may not always match the contract when it's fully executed, right?

35:10The data in that contract may have changed. And so we've also now been working on something called archive agent to help update the data field so that if you need to go and glean intelligence from that contract later in time, you can. Or, you know, by way of natural language search, the data in the repository is just parsed in a different way to be able to find the more global view of what it is that you're looking for when you're asking your repository if certain things are true about your contracts. So really trying to reduce friction that we've seen in the process and the experiences of our customers on the AI side in particular.

35:46Shamil Malachiyev: And when developing these technologies, like all industries, starting from manufacturing ERP systems, you know, products to like anything, whenever you try to give people AI features, they're like fantastic. They make the job so much easier. But that actually persuading people to start using them turned out to be like quite a challenge. How do you change people's, because people don't like change. You know, when you do something, you know, it's comfortable. When something new comes on, it's like, oh, it's risky. I don't know. How do you, like, as Iron Cloud, try to kind of force that, not maybe force, but help people go through and make that change?

36:28Yeah. I think part of change management, whether it's internal or external, is painting a picture of what's possible and explaining why certain things are true. So here is why we created this feature. And here's what we think it will enable by way of a different, better future for you and how you work. And once someone understands like, oh, I see what might be possible. I see why this is being offered. Then step two is, and now let me teach you how to use it. Let me make it easy for you by way of support guides, documentation, training sessions, live meetings where you can get together with other customers who are doing similar things than you, live sessions where you can come here from, you know, Iron Cloud's amazing customer success and customer support teams on how to optimize and use certain features.

37:19So enabling people with the information and skills they need to then go achieve what we've painted for them as possible, I think, is the connection to how we encourage people to continue to, I think, iterate and change.

37:34Shamil Malachiyev: And what are the parts of the platform that you personally are the most excited about? Yeah, I mean, so many. But what I'll tell you about in particular is the prospect of what we're working on with Jurist, and especially what we've got on our roadmap this year. As you know, Jurist is a redlining agent. I've talked a lot about that. But what we're trying to do with Jurist is really leverage the rich data sets that we have from customers to make the redlining and negotiation process seamless. So earlier I mentioned intake forms are the places where circumstances about a deal live. So who the vendor is, if it's a vendor deal, how much the contract costs, what exactly you're getting.

38:17And then lawyers need to also know, are you sharing PII with a counterparty? Are we giving them access to our company's systems? Things like that. So that context, that awareness of what's happening in the deal actually drives red lines actually drives the application of certain provisions and playbooks. So being able to connect how jurist applies red lines based on that contextual awareness, and then secondarily, based on understanding of your own company's precedence, how have you contracted with counterparties like that before in that industry? How have you contracted with that exact counterparty before?

38:54What do your own contracts say about how you like to agree to terms or where you push back? I think those things are really going to change the game for commercial lawyers and negotiating because it won't just be, oh, you know, let me remember the last time I did a deal like this and try to come up with the same red lines. Instead, the tool and the technology foster the ability to do that at a scalable fashion.

39:17Shamil Malachiyev: When looking at so many changes going on for, you know, people in the companies, I guess you have your own story of the burnouts in big law. I can imagine with trying to keep up with all of these technological advancements in the industry, there are a lot more people right now going through something similar when the expectations are tremendously high. When they have to start dipping their feet in areas which they didn't touch before, like technology, like business processes and systems. On the example of how you went about taking the time for yourself to refine yourself and come back stronger.

39:59Could you maybe share a bit about that kind of personal process and journey? Yeah. Yeah. Thank you for asking. I think what's interesting about my experience taking a break and becoming a spin instructor is this. When I first did it, I thought I had ruined my professional career. right? I, it was not as though I was so confident I would be able to come back and get a job in house and know exactly what to do. Instead, I left the practice of law actually believing like, maybe I'm not a very good lawyer. Maybe I chose the wrong profession. Maybe this isn't for me. And so for the first time I allowed myself to think about like, what is for me?

40:39What I'm not just checking something off the list, trying to chase the next academic or professional success. what actually brings me joy. And so I sat and I had never been a fitness instructor before, though I was a athlete and a dancer. I said, what do I love? I love fitness. So I literally showed up at a spin studio and I said, I love fitness. I'd love to teach a cycling course. And I had been a road biker in the Bay area. So I was pretty good at it. And so I said, you know, like, and I was a dancer. I love music. Like I think I could do this. And so thankfully this studio had an in-house training program and they said, you can go through our in-house training program and we'll teach you how to be a spin instructor.

41:19And what I know about myself as a litigator held true as a spin instructor. I believe I can learn anything. I can figure anything out if I put enough effort, time, and, you know, dedication in. So I learned how to be a fitness instructor. And for the first time, I felt real joy in my work because I actually was being paid for this, Right. And it's not to say being a litigator wasn't didn't have moments of joy, but I met every day people were high fiving and saying, thank you. And you changed my life. And I feel so good about myself. Right. That was a different way of living. And what I realized was my essence required that I have a job where I felt like I was building something, helping people, delivering something of value to the world.

42:05And the second thing was true, which is I, you know, I continue to hone this discipline of like, you show up every day, you don't give up. And so I knew that if I didn't go back to the practice of law, I would have felt like I gave up. And so I really leveraged my community. That's the second thing I'll offer you. It was like this joy and wonder guiding me and then community helping me find a way back to in-house. I said, I want to try being a lawyer again, but I want to work in house and I want to be a transactional lawyer. I want to be a litigator anymore. So I just talked to every single friend I had, every single contact that was willing to talk to me about their jobs.

42:42Anybody who was willing to give me an informational interview, give me advice, look at my resume, pass it along. And that community landed me. It was a former coworker that referred me into 24 hour fitness and it landed me that window back in. And I will tell you, it was not an easy path back in, right? It's hard enough to move in-house from litigation to commercial work. Way harder to move in-house if you're a spin instructor living in Las Vegas. Nearly impossible. So I made that shift. And I really think it was because I had that conviction of my connection to the mission of the company that I could tell that story.

43:21And two, because my community went out on a limb for me and I was able to leverage it and really move. And I think that, you know, I give you that example to say, like, that's how I made it through that moment. And I know that's how I continue to make it through every one of these moments of shift in career. It is, I have to have this connection to the mission. I have to care and be passionate about what it is that the thing can offer. And I have to rely on a community of people to help me get through. And AI is no different, right? So one, I truly believe in the power and potential of AI in helping lawyers practice more efficiently, more effectively, really demonstrate the incredible value that attorneys bring to organizations.

44:08organizations, I think we can magnify it by way of AI, right? Like I'm in the camp of this is going to make us even better. And I can find a, you know, that is my goal in life is to find a way to help legal AI transform the lives of lawyers everywhere. And it is not easy to use this technology or to know everything about it or to learn or to do everything. Like there's just too much out there. So I need to ask my peers. I need to ask my friends, like, what have you been building? What workflows have you disrupted? What tool did you do to do this? What tool did you do for that? Like, compare your use cases, compare notes, like there's always ways to optimize.

44:45And I think community is the perfect way to do that.

44:48Shamil Malachiyev: And two follow up questions to that. Like, whenever I talk to somebody who's really further, you know, on the journey of AI, they all think they're behind. It's like, the more you know, the more you think you don't know. yeah how you've personally like because you seem very self-confident person which is awesome and do you ever get that kind of like imposter syndrome when everybody's feeling like they're a bit behind and I guess maybe you get that too like personally as well how do you deal with that like keep your confidence up while you know navigating potentially the imposter syndrome Totally.

45:28Yeah. I mean, and that question exists with respect to AI and frankly, with respect to my profession. So yes, I feel that at AI all the time that like, though I know a lot, though I'm doing a lot, though I have learned a lot, I still sometimes feel like I am not at the cutting edge or that like there is more for me to do or like I'm behind. And the way I square those two things is I just keep trying. I just never give up, right? I use that same ethos that's like so buried within me of like, I will get up every day and I will try my best and I will learn what I don't know. And I will try new different things that I've never done before.

46:07And I will fail and I will get right back up again and do it again the next day. And that like relentless pursuits of knowledge, I think is really what helps me overcome the imposter syndrome. Though I don't know something today, I sure as hell will know it tomorrow, right? Like I am the person that will go find it out and learn it and figure it out. And that translates to my entire career, right? I have always had this tension of I'm an imposter. I tricked everybody. I don't know how I got here, but I did. And this deep-seated confidence that I can do anything. And those two things exist within me every single day of my life, right?

46:46and their intention. And I just have to remind myself that that voice that is trying to tell me I do not belong or I'm an imposter is also probably part of the reason why I'm so successful because I'm constantly trying to quiet the voice. And, you know, I'm in therapy to deal with that. But, you know, I think it's just part of the emotion. Like it's how do you control that voice and how do you harness it at the same time?

47:11Shamil Malachiyev: How do you make it your superpower? power. And you've also mentioned the community that kind of helped you get back on the horse for people within the companies. I think that is a very kind of valid point of if you want to get better, if you want to feel like you're not as behind as you think you are, it would help to kind of create a small community within your department, within your company. Have you done any kind of those like creating a small like AI council or people sharing like what you're building, what works, what doesn't work? Yes. Yeah. So I've done it in a few different places. One is within my own team.

47:52Actually, every single week we in our team meeting have people present on their AI use case of the week. So what are they using AI for that week? What are the prompts that worked? And like I shared earlier, what's a fail potentially? What did it work? What are you We also have an AI course syllabus that we have created for our own team. So we have done our own research to figure out what are the skills that we think we need to learn in the next three to six months? What are the classes we can take or the course material or the information we can ingest to do that? So we set up a syllabus that's like, okay, this month, you're going to learn about prompting.

48:32Next month, you're going to learn about MCP. Then following month, you're going to learn about developing agents or vibe coding or whatever it might be. And so we actually have set out a path for ourselves of what we're learning and then what we have to do with it to put it into practice. So by a certain date, you have to have built XYZ agent or XYZ connector and disrupted a certain workflow. So our own little team is an AI test case, right? It is how are we thinking about changing how we practice and deliver legal services to our customer, which is ironclad, by way of our, you know, our innovating with AI.

49:10And we have the benefit of partnering with our incredible EPD team to do the same thing, right? When we have ideas, we go to our engineering and product partners, to your point earlier, and we say, hey, we're having this problem. We have this idea. We think this could solve it. How can we partner with you to come up with these cool ideas? So we're lucky in that we get to expand that to engineers and product folks that can actually bring it to life. And then I'm a member of a few, you know, GC groups and women's groups where we have AI circles where we talk about, hey, how did you build this? Or how did you navigate this complicated thing?

49:45Or this thing isn't working for me. Can you give me advice on it? And so we're trying to meet on a more regular basis to talk about those things. And I also found that really useful.

49:55Shamil Malachiyev: And what would you advise people? Like, what is the best way of finding those groups? Because I feel like everybody needs an AI support group, like, I don't know, Claude Codders, Anonymous, I don't know, in their region. What would be the best way to kind of find the right group for you? Yeah, for me, it's start with the groups that you're already a part of, right? If you're a part of an affinity group or a bar association, ask, is there a subcommittee on AI? If not, start one, or if not, just start a group of informal people that are looking to talk about AI. So there's no, I think it's start where you already are and see what exists within those groups.

50:39And then if you really can't find anything, it's find the organizations that you want to be a part of that likely have AI components. So if for example, you're a GC of a tech company, L Suite is an amazing place to go. Or if you're an ironclad customer, you can join, you know, our online community. Like there are so many places where there are existing groups of people that might do the work that you do and which have subgroups that are specifically focused on AI.

51:06Shamil Malachiyev: And what are some of the coolest use cases that on a personal level that you use for yourself with AI? Yeah. I mean, first and foremost, I use Jurist every single day, right? So like two redline contracts. I think I've spoken about that at Amnauseum. I think it's really cool. I think it's amazing to get to see our company's guardrails put into practice and red lines on actual contracts that are live. So I think that's fantastic. Some other use cases. I mean, I use AI all the time for synthesis and quick summaries of information. So if, for example, I get added to a Slack channel and it's like scrolling back for months, oh my gosh, what do I do?

51:45I will drop that channel into Glean and I will say, give me a history, give me a quick summary of what's happened, where the issues are. I'm being looped in to answer XYZ question. What information in this Slack channel is relevant to my ability to answer that question? So, you know, that version of synthesis I do with basically everything, which is issue spotting, but customer says, Hey, I have a problem where I need to answer, you know, I want to build this feature. How do I do it in accordance with whatever the applicable rule might be. I then start with AI always. I say, this is the feature we want to build.

52:19This is the regulation at issue. What are the questions I should ask to start to figure out more about that, about it is, about that feature, about that tool and how it might comply or not comply, right? So using AI as a thought partner is a really neat, strong use case for me. A synthesizer, an intern is another use case, a sparring partner, like I'm about to send this email to my executive team saying XYZ, find all the holes in my argument, and then draft what the addressing of those holes might be. So as a sparring partner, as well as how I found AI to be really useful.

52:57Shamil Malachiyev: How often do you have to remind AI to replace EM dashes? And I know like the M dashes are a favorite thing within the legal environment. But now in order for that to not look AI-ish, do you ever have to be like, please remove them? I mean, I feel attacked as someone who has used M dashes my entire life. Now I'm like, no, that is not a signal that AI wrote it. Like all lawyers use M dashes. So it drives me nuts. I'm very sad. But yes, I do have to remove them because otherwise people assume that it was not me that drafted. And look, I'm not shy about using AI. I just don't want people to think that I didn't revise or make it better before I said it to them.

53:38Shamil Malachiyev: And I think a lot of listeners to the show, they run their own departments. And some of the conversations that I was having with like managers on my teams, I'd be like, we need to start kind of pushing and forcing people to start using AI. and he came back to me and he's like, we can't push people because we can kind of ask them but leave them to make the decision. But as a leader of the people, I was like, I need to start pushing them because it's going to be my responsibility in a year's time to, if you're not up to speed, I wouldn't have a choice but to find somebody who can, because there are going to be a lot of people doing it better.

54:17Shamil Malachiyev: How do you go about making that, I don't know, like tough love to help people adopt the right things at the fast enough pace? Because you are quite a competitive, sporty people person, but then other people on your team might not be. Yes. Yeah. So I do it through two things. One is the expectation, the requirement. So everybody on my team knows my expectation, my requirement, my express desire and ask from you is that you use AI to do your work and that you do it in a way that is ethical, complete, that you exercise your judgment. But my expectation of every single person on my team is that you are using AI to do your job.

54:59So I make that clear. But what I do is I couple it with this, what I'm calling enablement material. So I'm not just saying it, use it. You know, like if you don't, you're in trouble. I'm saying use it and let me give you access to all of these things to help you use it and understand why using it matters. That's why we built the core syllabus. That's why we have an AI charter that sets out our expectations with respect to usage, right? I'm enabling them to use it in a way that's compliant with our rules, how we think about AI, how our team thinks that AI can best help us. And then I'm also giving them access to information so that they can use it better and actually spend time.

55:41Like I'm freeing up time. I'm saying my expectation is also that you do this course. Like you need to spend an hour a week or whatever it is doing this material. And then I'm modeling for them, not just individual model, they're modeling for each other, right? By way of coming to our team meetings and saying, this is what I'm doing. And then people get to get a little sense of FOMO if they're not doing it. They're like, oh my God, that's cool. I want to do that too. So I think it's a combination approach. If all you're doing is setting the expectation, I don't think you're doing a good job at managing the change necessary to push towards AI.

56:14Shamil Malachiyev: And I guess you're also living by example at the same time. Trying my best, yeah. What are the things that kind of make you think that we might be living in an AI bubble? Because that's the kind of question that keeps popping up a lot in my conversations over the last four months, especially when you see companies emerging like Harvey, Legora, they came out of really quickly to valuations of 10, 12 billion dollars. And you see the industry trying to move really fast. But then when you look at adoption, people need time to, you know, get accustomed to all of those tools. In your personal view, do you think we're in a bubble?

56:53I'll answer the question by starting to say, I think that for legal tech in particular, there is a real need for the application of AI to what we're doing. Like it's a high leverage scenario. And so I don't think that the need for AI or the ability to apply AI to legal work is overblown at all. Like, I don't think that's a bubble because I think that we're already seeing the value of applying AI to our work and how it can change things. But I think to the meta point of like, in general, is there an AI bubble around, the value of this technology and the tool? My answer is no, because the tool continues to iterate and prove its value and potential delivery of success.

57:38It's what we're going to do about how AI performs that will dictate whether the decisions that we're making in relation to AI are the right ones or the wrong ones. And I think we're still early in the innings. Like we are still figuring out what AI can do, how to use AI best, how to make sure that we're getting the right and best return on our investment from AI. And so it really depends on what happens in these next months, years about that return on investment in particular and understanding the value to our day-to-day work.

58:13Shamil Malachiyev: And personally, as a last question, are you more anxious or excited about the future that AI is getting us into? Yeah, I'm more excited about the future that AI is getting us into. That's not to say that I don't think we have to exercise care and diligence in driving towards that future. I absolutely do think that's necessary. But the reason I'm excited about what AI has to offer is it can help eliminate some of the rote work, the administrative labor, the minutia that can really create burnout in our profession, especially. And to have someone else in a profession that can be really lonely is really useful.

58:56And when that's, I say someone else, but like going to an agent and saying like, like, hey, gut check me on this. Like, what's wrong with my argument? Or ask me questions back that somebody else might ask me. Or like noodling through things with an agent that gives you an instant response. I think it can make the feeling of practicing law less isolating, less lonely. And so I'm really excited about what AI can do for us as lawyers and for how we practice law. And I think it requires a lot of discipline and a lot of care to make sure that we don't lose sight of the very important personal aspects of the practice that we talked about earlier.

59:34Shamil Malachiyev: That's actually a really cool perspective that I haven't heard before than actually alleviating loneliness. Because otherwise you just have to spend so much time with just a screen and a lot of text, you know, thinking through it. And now you can almost have like an assistant or a buddy who's kind of helping you move through this. Well, I want to thank you so much. for the conversation today. This has been an absolute pleasure to have you just made. I want to thank you for sharing with our listeners. I think they got a lot of gold nuggets for themselves to take back into how to navigate this changing world of AI.

1:00:07Shamil Malachiyev: So thank you so much for taking the time to come. Thank you so much. Yeah, I really appreciate you having me. This was a pleasure. Thank you.