#32 - Ironclad CEO Jason Boehmig on Legal Ops, CLM & More

We all want to get things perfect, but the most successful legal operations folks are willing to do stuff that feels scary and get moving.

I don't want you to do the dishes. I want you to want to do the dishes. That's how I feel about the gcs. Like, I want you to want to own this problem. Hello everyone and welcome to Pearls on Gloves Off. Thank you for joining us. I'm your host, Marielle Carroll. Today I have on with me Ironclad's very own co founder and CEO Jason Baymake. We did something a little different today and rather than in our usual 45 minute or so episode, we recorded a long form podcast. You know, a little end of year experimentation and really some inspiration from the great podcasters like Joe Rogan and Andrew Huberman. I wanted to have Jason on because I have personally learned so much from him and continue to be inspired by his vision. You know, Jason and his vision were a big reason that I decided to join Ironclad in the first place. We really see eye to eye on why legal operations professionals and the community that we've built here is so important to who we are as a company and where this industry is going. Of course, we're going to start with Jason's personal journey, how we met, and how the rise of Clock through in parallel with the astronomical rise of Ironclad. It's been an incredible two and a half years for me personally here, and I hope this peek into our conversation shows you a little bit about why. Thanks so much for listening. Well, thanks for being here. It's going to be fun chatting with you.

Yeah.

I was just thinking back to when we first met. It was at the nuthouse. We actually met at a dive bar.

That's amazing. I forgot about that.

Palo Alto.

Yes. Which is no longer there.

It was the last standing dive bar, I think in Palo Alto proper.

Yeah.

Yeah. We met there through a mutual friend connection and it was during the day, so it's not like we were out drinking at a dive bar. And I think Ty was there too. So that was the first time we met. And when you guys came and told me about Ironclad and then I think you came to Google to show us it after we heard about it, but that's right, that was the first moment.

Yeah. Pretty wild. And I just noticed, like going back to founding moments, that's a founding moment. This table is the table from my apartment, my initial apartment that we like started the company around that we're sitting at is this actual table that has like been Reused in the office, so.

Haven'T seen it yet. It's like an IKEA table.

It's a $99 IKEA table that came with four chairs as well.

That is amazing. Somewhere over here we have to keep this for all of time now.

Yeah, exactly.

So you started Ironclad, what, like in 2015?

So, yeah, 2014 I quit my job, went to Burning man and then came back and started ironclad. September, early September 2014.

And you were a lawyer, but you also had like banking background too, right?

Yeah. So the catch up on me is econ degree, undergrad, didn't really know what I wanted to do. Went and applied to some investment banks in New York. I'd been to New York one time, like drove through it as a kid and got a job there, like packed up everything in a suitcase. I worked for Lehman Brothers doing banking and later sales and trading stuff. And yeah, moved to New York, shoebox apartment, had a great five year run there. But I'd always wanted to go back to law school and I thought I'd work at the bank for two years. I actually ended up working there for a little longer. And when Lehman catastrophically imploded, a lot of good lessons, there was kind of like the right time to go back to law school for me.

Yep, yep.

And then moved out to the Valley after that.

So you went to law school, you worked at a law firm and that's when like so many other founder stories in the legal tech world.

Yeah.

That are parallels. Like you go in there and you find out that you could do this so much better if you could use a little bit of technology.

Right. Yeah. So my initial thing that I wanted to do was not be a startup founder, but it was be a lawyer that used technology in the practice of law. Because I felt like that that could unlock a lot that, you know, everyone knows and knew back at the time was broken about the legal profession is it's not that satisfying. You're doing a lot of rote work and the stuff that you actually learn in law school sort of isn't relevant because a lot of it, you have to just pick up and it's like more mechanical.

Yeah.

So I, I actually like cold emailed the. I just looked up who the outside counsels were that were the top, like Facebook's outside counsel and Twitter and all that kind of stuff, and was lucky to get a job with this guy, Ted Wang, who's like an investor and advisor to Ironclad. And I still, I think I have a call with him. Next week, still in touch with him. And he kind of got that vision. Because what I pitched to these attorneys was, I want to be a different type of associate. I want to be an associate that might bill a few less hours, but is going to produce automation and efficiency with the work that I'm doing that other attorneys could use along the way too. So he was really like, forward thinking and to allow me to slot into a little bit of a non traditional associate role where most of the time I was practicing law, but I was also like working on tinkering. Yeah.

So you knew you wanted to do that even before you started at the firm.

Yeah. So when I was working at Lehman Brothers, I. It was sort of the rise of quantitative trading. And for the first time you had these MIT coders sitting on the trading floor next to the person who had been trading bonds for the past 30 years.

Yep.

And I was really fascinated by the people writing code. Like you could actually get all of these interesting insights into some of the securitized products desk. So it's like mortgage backed securities is the primary use case. And, and if you were writing code, like you could analyze every mortgage that was securitized into a particular security, and you could never do that with just like looking at it or reading it yourself. And I was pretty fascinated by like, wow. Quantitative, data driven ways of doing finance have like, revolutionized the profession. And in law school, I got exposed to the almost like hundreds of years of thinking that if the law is more of a science, it's better for everyone. And you can go back to things like the hand formula and just these principles that we should try to make the law more quantitative. We should try to make it a little bit more of a science because it's more fair. And I kind of just put those two ideas together of like, I just saw finance revolutionized by quantitative thinking and code. And there's a long line of jurisprudence that's sort of trying to do this, but it feels like there's an unfulfilled part of that. And so that was kind of like the two pieces of things, my Lehman Brothers experience and the study of jurisprudence in law school that put together the wanting to apply scientific methods and quantitative principles to the practice of law.

Right, right. So you started tinkering kind of at the firm and then shortly thereafter you thought, wait, I think I. I think I can go build something here.

Yeah. So that was the theory. And like the reality was like, the, the way you apply quantitative methods to law is like you just start with the low Hanging fruit. And you start with things like the. One of the first things I ever made at the law firm was a script that would auto create PDF red lines for you. Because I would. I went into workshare Compare, which was the thing that you use as a lawyer, and like, does all these fancy versions of a red line. And I think I counted. It was like 17 clicks to make one red line, which is insane. You and I connected, I think, in our first meeting, about number of clicks. And so I'm like, I'm making. I'm on an M and A deal. There's like 25 things I'm redlining times 17 clicks. I'm a lawyer, so I'm bad at math. But, like, that's a lot of clicks.

And a finance background too. So you're not that bad.

That's a lot of clicks. And I was like, there's gotta be a way to, like, do this with less clicks. Also, I hate that I'm billing the client for this because it's just dumb and like, no, but I don't want to be doing this. The client doesn't want to be billed for it. I've got enough work that the firm can, like, make money on other hours that are actually more legal thought.

Yeah.

So, yeah, I actually had hired a software engineer on hacker news for 50 bucks an hour, and he taught me to code on weekends. So I was like, learning to code on weekends. And then I would start hacking together this stuff. And after two years of doing that, realized I actually want to do more of this creation because that's where nobody's really working on it back at the time in 2014. And that's the kind of like, origin story.

Yeah. Which is amazing because as someone who has also worked at banks and worked in big companies, I mean, it's pretty brave to just decide you're going to start your own thing. I admire you so much. I look at founders and I'm like, wow, I could never do that. Like, that's brave. It's scary. And like, to leave, you know, well, paying good, secure jobs to go off on your own is, to me, terrifying.

Yeah. And I think it was even a different world back in 2014. And this stuff, like, I remember the Bay Area legal tech meetup.

Yeah.

And it was like two people, 10 people. And. And it was like the same 10 people all the time. And so this was not a, like, it's not what it is today. Of there's been successful companies. Like, this was more universally considered a bad idea. And then the tough thing is I think that maybe people don't talk about when founding lawyers. Founding companies is like one, I think lawyers tend to be a little bit risk averse. But two, you have a ton of student loan debt. I didn't have any help getting through law school. I just took out a ton of loans.

Yeah.

And I think I had like 180k or something of student loan debt. I also had some from undergrad just to. For good measure. And that's scary. That is really scary. You're starting a company. It's. No one's really created a path that you can follow on that. And you have a bunch of student.

Loan debt and yet you still wanted to do this because you believed in.

It that much or like what was I like really? And I tell other people thinking about starting companies this, like, I think you kind of, if you don't feel like you have to do this, like you have to do it.

Yeah.

You maybe think about, about how much it's gonna take. Like we're just getting started. I really believe that. And I'm lost it. I'm almost at 10 years.

Yeah.

And that is like every single time you go to a party, like you go meet people, you're gonna talk about this.

Right. Right.

And I fortunately love it. But I think that that's like an underestimated thing.

And, and you probably don't realize how much of an investment of your life it's going to be when you're, when you're starting out.

Right. Yeah. You don't. I don't think there's any way of understanding that unless you've started a company.

I just watched an interview, I don't know if you saw it, with the CEO and founder of Nvidia. And these folks asked him, like, knowing what you know now, would you go back and do it?

I saw that same thing. Yeah.

Would you found another company or would you do it all over again? And he was like, oh, hell no.

He's amazing.

He is amazing.

That's such a good clip. We need to like link that in. And at that time, if we realize the pain and suffering and just how vulnerable you're going to feel and the challenges that you're going to endure, the embarrassment and the shame and you know, the list of all the things that go wrong. I don't think anybody would start a company. Nobody in their right mind would do it.

But I get it from his perspective. I mean it is a lot to give up. So would you, would you do it all over again?

100%. I mean, I think I was just talking about this this morning. Like, the weird thing about Founding is it's like there's a lot of tough stuff. There's also amazing stuff. Yeah. And it's kind of like inseparable. It's like really hard and really tiring, and it's really energizing and really, like, exhilarating all at once. Inseparable.

And it has to be fun. I mean, I remember, I like what you said earlier about when you're starting something, you almost feel like you have to. It's not even a choice. Right. You don't even think about, should I do this or not? That's kind of how we felt when there was a group of us figuring out, should we make Clock an actual thing? There's so much momentum. And the feeling we had was, we have to. The world is asking for this. We're the only people who can do this right now. We've got to build this. And the rise of Clock was we started in 2016. Right about when you and I had met at the nut house at the dive bar in Palo Alto. And I think what we had talked about in that conversation was you guys have this amazing vision for this company. I was really impressed with just how different you and Kai were thinking about legal tech and the company that you were building. And I think that's when we said, we're doing this thing in Vegas in May at Clock, and you guys have to be there. And then you guys did. You showed up. What? I don't remember what month that was, but probably just weeks. Weeks later.

Yeah. And maybe you even got Vegas.

You got, like, the last booth that we had available. I feel like we did. Cause it was a very last minute. Like, we had just met, and I said, you guys gotta do this. Yeah.

Back of the room.

Like, back of the room.

Yeah. And that was. What was so cool about that, is you could really feel the founder vibe. And I think it's almost like there's. It's a community of founders right in the Clock world. And I think I remember it was either that year or the following year that we actually got a couple of our investors to come out because I wanted to see this. I don't know if you know this.

Yeah, I don't know that.

But yeah, Steve from Excel came out and I think somebody else did as well. And it was really interesting to get their take on it because they were like, the passion here is 100x what you get at another conference. And it's amazing. And then the thing I was surprised at is they're like, this is also so small compared to other conferences. And, like, you can just tell it's going to be big.

Oh, that's so cool.

I mean, the venture investors can kind of, like, spot that. And they were spotting it with Clock.

I wonder what year they were there, because. Let's go back. So you were there our first year at the Bellagio. I think you guys got the last booth, so you had, like, the worst physical positioning in the sponsorship hall. And I remember I was excited for you guys because we had met and I knew you personally and you guys were like, let's do something different to sort of attract people to our booth. And you guys brought in an external company to be. Was it like Phil's Coffee or someone was barista ing like.

Yeah. So that wasn't an external company. That was us. That was me pouring pour over coffee, actually. The pour over coffee. So this is the founding desk. The pour over coffee thing is still here up on the sixth floor. Oh, my God.

There's all this that I don't even know about. Our own company.

Yeah. So that was software engineers. So we brought software engineers. It's basically half software engineers and half business people. And they were pouring coffee.

Coffee for people at Clock.

Yeah.

And then I think I had to personally come over and reprimand you guys because we were not allowed to have external food and beverages in the.

Yeah, I think we did get. We did, like, bend a rule on that one.

But it worked for you. It's to the table. Okay. And then amazingly, you know, Clock obviously exploded. But I love how the rise of Ironclad is so sort of intertwined, like, because year over year, you guys had a bigger and bigger presence, maybe even brought your investors in at one point. But I think in the last couple years, even. Even the year before the pandemic, when we had to put everything on hold. Yeah, you guys were what, like a diamond sponsor, Biggest booth on the hall, on the main stage. And, you know, so much growth in the little time between the time that I met you and then.

Yeah, true. And I think, you know, Clock has been a big part of what we want to do here. And I think going back to the early days of Ironclad, so Kai and I met, we got into Y Combinator and, like, one of the only legal tech companies to come through Y Combinator at the time.

And Sam Altman was president at the time.

Sam Altman was president. Yeah, definitely. That's how we got to know him. And one of the YC has a couple YC isms that are just proven wisdom from the, I guess, thousands now of startups that have come through. One of them is like, it's better to be liked by a small group of people than, or, sorry, it's better to be loved by a small group of people than just merely liked by a lot more people.

Yeah.

And we kind of like really took that to heart. And then CLOCK was where we're like, we want this group to love us and we see something here that we're going to bet on as well. And that's the rise of the legal operations professional. And that's going to be who loves Ironclad. And we love them.

Yeah, yeah, yeah. And that was different. And just for everyone who's listening, because I don't know that everyone knows what Y Combinator is. You know, we're all in Silicon Valley, so we know them very, very well. But for everybody else, what is it?

It's. It's the premier startup accelerator and there's a lot of startup accelerators now, but I think they kind of invented the modern startup accelerator and it's where like Airbnb, when it was a three person company and like an Airbnb in the founder's apartment in San Francisco, like they got their start through Y Combinator. Dropbox. I'm trying to think of some of the other companies. Stripe. Exactly.

Tons. Tons of big companies now.

Yeah.

Instacart, maybe.

Instacart, yep.

Okay, so you guys decided you're going to be a legal tech company. The focus, at least initially was on the legal Persona and Legal Ops even specifically and making this something that they would love. And why, why was that so important? Because knowing, I mean, we're talking about a contracting system which touches everybody in the entire organization.

Yeah. So I think there are a couple parts to that. So one is we felt like it was important to be the number one solution for a group of people. And, you know, Legal Ops was a group of folks looking for solutions that there weren't a lot of people building for legal operations at the time. And so part of it was the YC DNA of like, this is a group that we could be number one to and we think is providing a lot of value and that value is only going to increase dramatically over time. So, like, this is a really interesting segment of the market to be in. The second piece was around kind of a core insight that we had, which is taking something that is like a single player desktop experience and making it collaborative. And now I think we've seen this with other companies who were started around the same vintage of Ironclad. There's a company called Figma that I think is a good example of this, which is we're going to take a design file that used to live on just the desktop of a designer in sketch, we're going to put it in the browser and all of a sudden like make design more collaborative. So instead of just being a thing a designer works on, it's going to be thing a designer collaborates on with the marketing team, the community team, and that's going to dramatically increase the number of users of design files at the company. You know, obviously we see that even more with contracts. We said we're going to take this thing that used to be a Word file on a lawyer's desktop, we're going to put it in the browser, we're going to make it collaborative. And then all of a sudden you have like AES collaborating with the legal team, you've got the marketing team collaborating with legal team, you've got the finance team team collaborating with legal team. So I don't say that we're not legal tech, but I think legal tech is limiting because legal tech implies you're used by just lawyers and lawyers and legal ops professionals are really important part of our user base and we want them to love us, but we also are fundamentally taking something that used to be not collaborative and should be collaborative and thereby expanding it to the whole company.

Yeah. And what, I guess to go back a little bit, what made you want to solve the contracting problem in the first place? I mean, you're explaining how it was in that collaborative and I agree. I mean contracting is broken. You can ask anyone in the entire company of any company in the world and they will tell you it is not a great experience.

Yeah.

So it's a, it's a clear problem. But what was there like a one moment for you or like why, why was this the problem that you wanted to solve?

Yeah, I think it's so foundational and I was kind of like one just kept going down the rabbit hole on it of, you know, obviously the initial experience was as a lawyer and a lot of what I was doing was making unstructured contract data structured. If I was doing the series B financing for a company, I would actually have to comb through their employment contracts and make sure that certain conditions were met and maybe represent those in a spreadsheet. And it was just manipulating data and turning these like long form text documents into structured quantifiable pieces of information. And I just realized, like, at the abstraction layer, like so much of legal work and so much of corporate work is manipulating data and contracts.

Yeah.

And turning it into structured form and then like having that structured form go throughout the company. And it was kind of this insight of like, wow, this is a problem, if it was solved, would just be a massive unlock, not just for lawyers. Like, one, it could change the entire profession, but. Or the corporate part of the profession at least. And then two, like, this could be a massive accelerant to companies because every function, like the finance team, think about something as simple as revenue recognition, where you're really like, reading a contract, understanding how that fits into a revenue framework. And this is a very manual process at most companies. But there's no reason why that shouldn't be an algorithm that just runs on the top of your contracts and takes that structured data and like, interprets in. In a way that is useful for the finance team. So was kind of like fascinating at how foundational that problem was once you started seeing it through that lens.

I remember the time that we first met and you were telling me, you know, the vision of what you wanted to build here at Ironclad. And people ask me all the time, why did you join Ironclad? And I go back to that moment. Like, I knew, I knew you guys had something. I knew you guys were going to be something big and that it was going to be different because of the way that you were thinking about the problem. And it wasn't technology for the sake of, like, let's just make things faster, let's just make things more efficient, let's just make things cheaper. It wasn't just about, like, as I always say, automating a broken process.

Yeah.

You were like, the whole thing is broken. What is the purpose? Like, going back to the why, like, why do we even have contracts? And you've, I know, spent a lot of time thinking about, like, why contracts even ever first came into being and what they, what purpose they serve and how they could be turned into data and how they can be thought about differently. That has always stuck with me as a very different perspective than a lot of other sort of technology companies that we're seeing in our space today. Which is what really attracted me to the company because I, I, like, that's something I can get really excited about. And I think you're absolutely right about it. But yeah, I guess. Tell me your thoughts on it is broken, but we're not just trying to speed it up. Yeah, what is it going to look like, I guess in your view?

Well, the thing that continues to really fascinate me about the contract is how foundational it is to the way that we work in another life. I sort of wish that I had Kai's brain, my co founder and was good at physics in addition to software engineering. But like physics is one of those things where I know just enough to like if you know about physics, you see the world differently. We're looking at a table here, but like really like this is molecules and atoms and like there's so much more that's maybe not obvious, but once you, your mind starts to see the world that way, you can't unsee it.

Yeah.

And I think that's how it has been with contracts for me. Of like we don't even think about this but like the reason we're sitting here is because there's a contractual relationship and like that is mutually beneficial for both of us and like we're able to work on interesting problems and like receive economic benefit and like support our families. And there's like, we don't really think about that, we just think about the relationship. But really like that relationship doesn't work without the formality of a contract behind it.

Yeah, very true.

And that is everywhere. Like shareholder agreements, like think about ironclad. And this is actually an anomaly in history. The fact that we're able to work this way, like the corporation and this, this binding together contracts is a relatively new sophistication to this technology that's existed for thousands of years. And I'm just like really fascinated by that. I'm also fascinated by like, what if contracts could get even more sophisticated, like what ways of working would be possible? Like an employment relationship is a relatively new thing to be this pervasive and this sophisticated in society. And I go back to some of the initial first contracts in history, Ancient Sumeria, when the contract first came out and the technology was first released and people started stamping these symbols into clay tablets and recording transactions in them. I like to think about the people who are working with the new technology and, and weren't. And you could imagine this group of people who's trying to remember everything in their heads about these increasingly complex business transactions where like grains arriving in 60 days and like you got to have the payment ready and like it has to be turned into beer, which is like a primary resource back then. And the people who had the clay tablet, like they would just be operating so much more efficiently.

Yeah.

And they could also like get Money lent to them easier because they could show exactly what that transaction was. They didn't have to like go explain it to someone and like hope that they believed that this green payment was going to arrive. Like you could actually see the mechanics of the transaction. And I am just kind of amazed by this concept and want to enable increasing layers of sophistication on it for future humanity.

But I feel like we haven't come that far from the cuneiform tablets to spreadsheets.

Yeah.

The way people are tracking things and keeping them in their heads, but now they're on spreadsheets and how much further we can go with that.

Yeah. And I think like, we need, in order to keep pace with business and the way that people want to work, we do need new mediums for the contract and new ways of recording it and accessing it and understanding it.

Yeah. What would you say to the people? I have so many conversations where people are like, yeah, clm. So interesting. Makes a lot of sense. Our company needs it. Everything's manual through spreadsheets. But you know what, it's okay. It's not that broken. We're getting by. I feel like there's urgency and, you know, I can give a 30 minute dialogue about why you need to do this right now and why it's really important. What would you say to someone who's like, eh, it's not really broken right now.

I think this is maybe an area where I will give an unexpected answer. I think it's fine for people to do whatever they want to. Like, I don't think people need to adopt AI if they're not ready for it. I don't think people need to adopt CLM if they're not ready for it. I do think like that the macro trend of history is going to be digitization of contracts, increasing complexity of contracts, increasing volume of contracts, which you're going to need technology to deal with. But I'm not one who's like pounding the table that people have to move on to something that they're not ready to. I kind of think like, well, you're.

Much more patient than me. I'm like, what's wrong with you people?

But there's enough people who are doing that. And like, I'm more excited. Me personally, I'm more excited about the people who are already bought into the clay tablet or already bought into the modern digital contracting platform than the folks who need convincing. Like, I like to stay on the. With the innovators.

Yeah, okay. And then let me just go back to the legal ops world, which is near and dear to both of our hearts and the sense of community. So obviously you hired me to help build out what was already there, though. So we, when you guys first started the company, community was always, always going to be a big part of the ironclad, I don't know, ethos and all. Where did that come from? Because even looking around now, there's not a lot of companies that have a community focus. But you had that in 2014 or so, right?

Well, there's a lot trying now. And I think this is one of the things that we talked about when we were inventing this role here together was, hey, I think we're not just going to do an interesting thing at Ironclad. Like, we're gonna help invent this for the whole industry. And I think, like, you know, our investors portfolios now come to you as someone who's figured this out.

Yeah, yeah.

But, yeah, community, in some ways, this is the great thing about working on a unappreciated problem is you really do have more time and space to explore the. The problem then. Like, you know, in some ways, I think the AI startups right now, it's exciting, but it's also like, it's such an obvious thing to be working on that it's a very chaotic environment. Like, there were no other companies in 2014 working on the same thing that we were working on.

Yeah.

And there were also, like, it was hard to get people that were interested in what we were doing and potential customers. So what we said is like, we believe in this space. We're here for decades. Let's get to know people and let's understand not just the problem, but the people behind the problem. And that kind of like, desire to learn and understand was the early origins of community. And the first iterations of this were like, hey, I wonder if people would show up if we bought them dinner and then we would invite, like, our software engineers and designers. And we just started having these interesting conversations and I kind of like snowballed from there because there is this really, like, special group of people that are working in legal departments, and I think they're very interesting and likable once you start to get under the surface, as you know, so that we just kind of kept building on that momentum.

Yeah. And you and I talk about all the time that we want to be the company that understands that customer, that Persona better than anybody else. And I think we. And that's. I consider that a large part of what my role is here is like, trying to really be in their shoes and convey that to other parts of our company. So our customer success, our product team, everybody kind of understands what is happening in legal departments, what legal Ops are thinking and what the challenges are. And how can we, as a company, as a product, help to make their lives better, but also as a company and a community, what we can do to make their lives better. And that's been a big focus of ours.

Yeah. So, I mean, to go back to some of the Clock stuff, how's it been for you being a founder and going from just getting a bunch of casual people together around a table to talk about Legal Ops to where we are today, which is like Clock, which you are a founder of, is its own giant and impressive organization. You're obviously like, have started something new at Ironclad in the community function here.

Yeah.

Tell me a little bit about that journey.

It's been really rewarding. And I go back to kind of what you said earlier. Like, it's not even a. It doesn't feel like a choice. Like, it feels like I have a responsibility to advocate for the legal ops profession and to help better define it, make sure it stays on the right track, make sure that it's viewed as a senior executive strategic role in an organization. And I. And I enjoy that. So it's. It's like you said, it's work, but it's fun and it's my passion and it's what I want to do. And I feel like I've been very lucky. You and I talk about this all the time, that I have a CEO like you, Jason, who really gets it, who understands the value of the community, the value of having this role at Ironclad, and also just the ability to. I don't go out there and talk about Ironclad much at all. I don't have a podcast that's about clm. I think it's really about advocating for transformation in this space and modernization and investing in legal operations and really thinking about how can we deliver legal services differently. That's. That's kind of my. My soapbox. And everyone here has been very, very kind in giving me that platform that I think I can do it even better here than I was able to do it when I was at Google and Clock. And I say that because, I mean, even the title of this podcast, Gloves off, there was a lot of stuff that I don't feel like I could say, you know, honestly, authentically, because of. I had Google behind me. And I also had to be very fair to sort of everyone in the CLOCK ecosystem. But now that I'm here, I feel like I speak on behalf of Mary and can really sort of say, here's what I think is broken, here's the mindset that needs to shift. Here are the things that are going to change and people might not want to hear it, but this is what we need to do. And so I feel I'm very blessed to be in this role and I've been given a lot of freedom to do that. And I think I'm uniquely suited because of what Ironclad has allowed me to do, to sort of be that advocate. Whereas, I mean, obviously the amazing board at Clock is still there and also all these other people in our community who have also stepped it up and are sharing and being very vocal. But I still think that I can say things that even they can't say. And they call me all the time and they're like, thank you for posting that or thank you for saying that because we can't say that. So it's been great. And I feel like it's just a continuation. Like I've been on this journey from the in house side to trying to create a global community to advocate for this. I was at the law firm before that and then now doing it from a legal technology company side. And you know, another reason I joined Ironclad is because I really think that we're finally at the point and when you and I first started talking about this role, I kind of could feel that we were at a tipping point in the legal ecosystem that there was like new technology entrants, like new interest of course from all the venture companies. But coming in to create this no code, easy to use, something that's really focused on the user, which to me is going to be and is already this big driver, this catalyst for the change in our industry that's here. It's kind of been coming, we've been talking about it for a long time, but tech was always kind of in the background as something that could enable a lot of change in people and process. But I think tech is now the driver of the change and especially with AI, and we should talk about AI, but digital transformation being the topic of every conversation, it's going to be the tech, good tech that is going to push people to want to change, which is so exciting.

Yeah, it is pretty wild time. And what do you see as next for Legal Ops, which has gone from the ragtag crew of rebels to a mainstream thing now?

Yeah, well, this is, I think we're in a really important inflection point. And had Bob Mignonelli on the podcast earlier this year to talk about the shift into strategic ops. And I, you know, I talked about this at clock a couple years ago as well. We have the opportunity to separate ourselves. We're maturing as a function. So the day to day running of the trains is happening. Like that's really important as a foundation. But can we step out of that and step into more of like the strategic thought leader being the right hand of the general counsel and really helping to steer the rest of the company? And you know, going back, that is why technology like CLM ironclad is so important. Because the data that you're able to now play with, capture like have access to for. Honestly, the first time ever, ever in an organization by anyone, not just by legal, is going to give you insights into how to run the company, not just how to run legal. So that's what really excites me about why I think CLM is really important as the first step for legal ops in order to get that impact to the bottom line of the company.

Yeah. I really do think that there's a kind of rise of the OPS function broadly. Yeah. Beyond legal ops companies. Yeah. And there's almost like a convergence where it seems like the leading legal ops folks are like starting to collaborate more with the revenue ops people who are absolutely critical to running a revenue function. And it really seems like we're in a dawn of a new era of the importance of ops broadly at companies, which is cool.

I think so too. I used to wonder if there would one day be like a centralized ops function where you had sales ops, finance ops, legal ops, like all reporting into a coo. I haven't seen that yet. I've seen a couple companies expand legal ops to be like more GNA ops, some with sales ops, but we'll see.

Yeah. Exciting times.

Exciting times. What are some? What would you think in terms of giving advice to our community? Are the keys to success when they're thinking about technology or even.

Yeah. So I mean, I kind of think like momentum is underappreciated and we all want to get things perfect, but the most successful and impactful legal operations folks are ones who are willing to honestly take a risk and do stuff that feels scary and get moving.

Yeah.

It's kind of like what's the Mike Tyson quote like? Everyone has a plan until they're punched in the face or something like that.

I don't know that quote, but I like it.

Yeah, exactly. Relevant to the title of this. And I kind of think that's right. Like, you never know how implementation or launch is going to go and you learn a ton of stuff. So getting stuff out there early, taking risks, rolling with the punches, and those are the ones that, like on iteration 5 or 6, are light years ahead of the kind of more careful approaches that might try to get everything perfect on the first touch with reality. And I think that that's kind of underappreciated. And now, you know, having seen this thousands of times.

Yeah.

What separates the top 10% from everyone else is like the willingness and honestly, skill. Because there is a skill there of getting stuff out there early and often, even at a big company.

Reminds me of the conversation we had recently about how the founder life and the legal ops life actually has a lot of parallels.

Yeah.

Yeah. Because you're the one who kind of made that sort of aha moment. What made you think that?

Well, I think. Yeah, I realized that. And one of the reasons why I think community is so important here is it is kind of an isolating function.

It's so lonely. Yeah, yeah.

And it is kind of misunderstood in that, you know, I imagine if you're a legal ops professional and you go to a function where there's a lot of other job titles, people are like, what's that? And so what are you doing again?

Yeah, Community is no different. But.

Yeah. Yeah. And I think that there's really exciting stuff like that. Like you get to invent the future and you kind of have a ton of agency and control, but it's also like, misunderstood. Like people don't get it. And so I kind of feel like it's a similar emotional journey to being a founder, which is a lot of. A lot of agency, but a lot of lack of understanding by a broader audience about what you're doing.

Yeah. When I first started here, I think I remember saying to you, like, God, CEO and founder, it's such a hard job. It's got to be so lonely at the top. And I felt that when I was running clock, because you only get the problems everyone comes near, all the problems of the day. No one ever calls you up and says, can we talk? Something really good happened in our department today.

You know, I'm curious what the. What your read is on legal ops and AI. Obviously, you know, I talked about the clay tablet revolution back in the day and the groups of people that were using clay tablets and the groups of people that weren't.

Yeah.

And just what an impactful piece of Technology that was. It feels like we're on the verge of another one of those with AI where very early days. Yep. But you know, what are you seeing in the legal ops community?

I think there's a lot of interest, there's a lot of buzz, there's a lot of pressure from above for the first time.

Yeah.

And I love that. I mean, I think when digital transformation is a buzzword first came that was a big driver of hiring for legal ops and investing it in and wanting people to leverage technology. And AI is just like another accelerant to say, what are we doing? Why are we doing things the same way in legal and how are we going to be doing it differently? I actually think the adoption and the real use, we're still very early stages and I honestly think it will take a while before it truly transforms how legal departments work.

Work.

But it's there and there's curiosity and to me that's, that's the biggest gift that we can have is like having people have an open mind to what can AI or tech do to change the way that we work day to day. I mean, you've been thinking about AI for a decade or more probably by now and been very, I think, intentional about when and what we rolled out as a company. But how are, how are you thinking about it?

Yeah, so I, we're correct. Have been thinking about this for a while and dating back to when I was at the law firm and this is the second or third, I guess, depending on how you measure it, AI wave that I've been a part of. And wave one was like Watson, remember Watson? And the initial excitement about that. It was like winning jeopardy and producing some pretty interesting results. We had seen that initial promise of AI and were excited about what it could do for contracts. Obviously like going back to the theme of structured data and trying to create that from unstructured long form text. Yeah, obviously AI seems pretty impactful and interesting technology, but yeah, 2014, 2012 was like the initial observation around AI. We started the company Ironclad AI in 2014 and what we realized was that AI back then wasn't quite where it needed to be to meet the standards of legal professionals, which is really high.

Standards, really higher than other areas for sure.

And I think we still see this to some degree of if you're just to take a concrete use case, doing a legacy contract import, which is taking a stack of PDFs and getting it into structured searchable data. If 10% of that data is wrong, but you don't know what 10%? It kind of like invalidates the usefulness of all of it and it just goes, it might be a cool demo, but you're not going to rely on the data set if a random 10% of the data is wrong.

Yeah.

And so the standard has to be like 99% for it to really be useful to legal professionals and like trusted.

Yeah.

As a piece of the operating rhythm. And you know, we, we couldn't get to the 99% with AI back in 2014. So what we realized is like the way you can get to 99% is by helping people with the actual work of creating contracts and with workflows. And if you're actually structuring the data from the get go, you're at 100%. So that's kind of why we focused on, for the early stages of the company workflows and using those workflows to power structured data in a repository. And we never stopped working on the AI. So it's been, we're on, yeah. Like nine and a half years of AI development. I think what's been really great about that has been with this new wave of generative AI, we have had a lot of the data infrastructure and foundational work done and we're able to layer on the new interesting parts of the technology along with like some of the proprietary models and things that we've been working on for quite some time. So this like combination has been really powerful.

Yeah. You know, the workflows. It's funny, I've only been at Ironclad for like two and a half years and in the early days when people were like, do you guys do AI? Like do you have it so you can have a requester answer a bunch of questions, but depending on how they answer something, it gives them a different template. We're like, yeah, that's just conditional logic.

Yeah, exactly.

It's not actually AI. So there was, for a long time there was a confusion out there, just misunderstanding about what AI actually is, what workflows and automation could, could already do a lot of like, what seems like magic to a lot of folks.

Yeah, I think we've always been very focused on delivering a result. And where our question has always been, what's the best technology to deliver that result? And I think where I see other companies going wrong is they put the technology first and then the results second. And this is also where I see like deployments go wrong. If the purpose of the deployment is to use AI, Right. It's not going to be successful. Right, right, right. You have to know what you're trying to accomplish and if AI can help you accomplish that in a more effective way, that's fantastic. Yeah, but we've always thought about it as a business problem and what's the most effective technology to apply. And there are still some use cases where like simple workflow automation is going to get you a better result than some fancy AI demo.

That's right.

Now the results that AI has been able to deliver have expanded by more than 10x.

Yes.

Recently and like there's some very exciting things going on.

Yeah. And because we were so intentional here. So Kai, who's your co founder and our chief architect here, he is our sort of AI expert, kind of been on the cutting edge of things for a long time. In the first like year or so that I was here, we were hearing from, you know, being out there talking to customers, talking to people out in the legal ops world. Everyone's like, AI, AI, what are you guys doing on AI? And I kept coming back to Kai and be like, Kai, my God, we need to invest, we need to do more AI. We gotta do everything when it comes to AI. And he kept saying, trust me, trust me, there's something coming, there's something coming and we can't do it as well until this comes and we should just wait for it. And I was like, we are wasting time. Like I said, I'm very, very impatient. And then Kai's like, it's here. And you know, like overnight we're hearing open AI and chat GPT and all this stuff in the news and I go, is that what you were telling me about for like all this time with big words? And I couldn't understand. He's like, yes, it's here. And then everything, you know, that we built happened very quickly.

Yeah, yeah, There was a lot of smoke and mirrors there for a bit where you know, there would be a AI result that would take four weeks to deliver and you're like, you know that's not AI. Right. They're just telling you it's AI. It's a human behind the scenes.

Yeah.

Screen. And we, we kind of knew that the actual AI and kind of a game changing piece of technology was coming. And thanks to Kai who I think another thing that we've been able to create a model on is the co founder who goes from doing a lot of things to just deep focus on AI. So Kai spends 100% of his time on AI now. And you know, we know Kai, but for folks who don't, he's Got two CS degrees and a physics degree from mit. Like Critical Palantir engineer, incredible technical and business mind. So having a co founder that has the mandate to do that has been really powerful. And I think the internal credibility and credibility with customers to make big company defining bets around it has been impactful for us.

Is that something you came up with? I mean, I'm always impressed with. I've told you this and, and now it sounds like public sucking up, but you are such a great leader and CEO. And when we heard this, even as I was interviewing from all of our board members who are working from Sequoia and Excel and Bond with some of the greatest CEOs out there, the fact that you're like, we need to focus on community and we want to make this a big core area of the company. We want our co founder to focus on this. I mean, you even have an executive coach who we're going to have on the podcast soon. Yeah, she's going to come on. But like you, you said all of our executives should have access to an executive coach. I mean, all these things that are, I think, pretty unique in. You're not taking, you know, some SaaS playbook from one of our, I don't know, some company that you look up to and saying, like, rinse and repeat. I want to be like that company. Where do you get these, like, visionary ideas of yours? I think it's really admirable.

Well, I think part of the art of it is knowing what to invent and what not to invent. And, you know, we don't want to invent a better way to do enterprise sales. Like, there's a fantastic way to do enterprise sales. It works. What we really want to do is be excellent at running that playbook. And then community, there's not really a playbook on that. So that's going to be one of our chips that we're going to spend. And I, Kai and I have talked about this before, but I've kind of have a viewpoint of like, at any given point, you have just a few innovation chips that you're going to play.

Yeah.

And being really smart about what those very limited amount of bets that you're going to make. Our community's been an innovation chip. We're going to go invent that, we're going to like hire you, we're going to hire Alex, we're going to do this, like stuff that hasn't been done before, but you can't do that in order to really do that. Well, in some areas, you can't do that on everything.

Yeah.

And I think the real secret is hiring great people. Like everything is easy if you hire great people and everything's hard if you don't have the right people. And I think we've been really lucky to kind of have this snowball effect of we've had a few great hires. You know, people want to work with Kai, people want to work with you and we're able to attract some of the best talent in the world to the company. And stuff is just easy when you have great people who pass the ball and support each other and aren't in it for the individual glory but are in it for the team. And I think we're all just ironclad first and industry the customer first in the way we think about things. And like if you're smart about your innovation chips and you have a team oriented and customer oriented mindset, a lot falls into place beyond that.

I definitely feel that, I definitely feel it's a team environment and an ironclad first. And I want to say here that everyone gives me credit for bringing Alex Su on and to build this community function with Alex. And I'm like, I had nothing to do with it when I was hired. Jason already said, by the way, I'm also, I've also found this other guy that's going to be part of the community team with you. So that was, I was all you're doing in thinking Mary and Alex together.

That's not really true. That was totally like, I give you a lot of credit for that. Like sure, I had talked to Alex before but like it doesn't happen without you here as well.

Well, you should take credit for that. It's been, it's been a lot of fun. So let's go back to AI for a second.

Yeah.

You also just recently published an article about the future of the profession. Yeah, Law firms specifically, but then also thinking about legal departments, like how what is AI going to do and how fast or slow do you think the change is going to take place?

Yeah, I mean I think this is going to be truly transformational to the legal profession broadly and there's not going to be a legal job that is untouched by AI.

Yeah, I agree with that.

I think it's going to play out differently for in house legal departments and corporates and for law firms. So I think with in house legal departments it is going to revolutionize the efficiency of the work and most importantly, it's going to give legal departments access to data and the ability to communicate that Data outside of the function. And I think that this changes the role of the legal department from one who's kind of the department of no stereotype that we always know about. And Alex has some great TikToks on to one of the most interesting data sources in the company. And this is kind of like mirrors the rise of ops. Ops is becoming a lot more important because running a modern corporation is about math and data.

Yep.

And the legal team has had no math and no data to contribute and has only had policies. They're starting to be able to tap into the biggest underground source of oil at the corporation, the contract. This is your customer list, this is your employee list, this is your revenue. This is the dollars in, the dollars out. And we're helping drill those wells to that oil data. And I think that's going to be like fundamentally transformational to the legal department. Yeah. And that's kind of the role of AI is like, let's make this, this data accessible and able to be manipulated and created.

That's right. So like the data in that. The oil. Right. The gold. That is the data. I totally agree with you. I think this is what is going to transform what legal departments do, what their charter is in a company. And AI is allowing us to get access to that where it wasn't accessible before. And people say, oh, you could, you could look for it. It just took a long time. You can't. Like, if you really have a big company and you want to find out something, you can't hire enough people. You could hire like 100,000 people to work day and night to read through the history of all your contracts and then manipulate it and try and figure out trends. It's actually impossible. And now you can do things with the push of a button. Very realistically. What are some of those things that you think are going to be surfaced when you have access to that information that we've never had access to before?

Yeah. So there's a couple of things. Like, one, I think there's going to be more of a gravitational pull of senior operational leaders to legal ops and the legal team, because the best CEOs in the world are the CEOs that are ruthless and curious about what new data they can get.

Yeah.

And they're starting to realize, I think this is like very, very early days, that the legal teams are an incredible source of data and that specifically the contracts are an incredible source of data. So I think that's one trend. I think another trend, and this will relate to the law firm side of Things is we're going to see the rise of the quant lawyer and the data driven legal team and we're going to see a lot higher quality decision making and like consistent decision making. Like I think everybody knows right now if you're at a big company and you go get a contract reviewed, it's very dependent on which lawyer picks up that contractor review of how they're going to review it. Now maybe they're operating on some like sort of unified playbook, but you're really getting the person and I think what you can start to get in the future is more of the algorithm that as it's delivered through a person and supervised by a person. But we're going to see more quantifiable decisions and I think we're going to start seeing trade offs. Like hey, if we put this term in, the data says that it's going to add seven days to the deal cycle time and it's going to reduce our risk by 23% percent. What decision do we want to make? Do we. If we're six days from quarter end, I don't know if we want seven days added to the deal cycle. So maybe we're okay with 23% more risk on that contract.

Yeah.

And this is like exactly mirrors the rise of quantitative finance and the traders looking at MIT coder data on the trading floor and making better decisions about trading bonds because you couldn't look at the mortgage tape and go through every single mortgage payment in a big securitized MBS deal. But you can go through that algorithm. So I think that's going to really start in legal teams and we see that like literally today. This is not a sci fi idea. This is happening. The data is coming back. We've got lawyers negotiating contracts 20 times faster and better on the platform today. This isn't like a magical idea. I think what we're going to see over the next 10 years is that innovation flow through to law firms and the business model and economics change around law firms. So people have been predicting the death of the billable hour for Is it.

Actually going to happen, Jason?

I don't think so. But that's part of the reason why I think that this is actually going to change because it doesn't require a different economic model for the law firms. I just think it is a different capturing of value at the law firms. So I think if you look at law firm economics right now it's the billable hour. It's how many hours you bill your customers and the way that partners can expand beyond the number of hours they have in a day is they can be have responsible associates below them that bill out more hours and they capture some percentage of those hours. And it's a pyramid structure. So you have one partner at the top, you have many associates at the the bottom. It's not great for, for anyone. Like the partner's actually losing a ton of value because they have to pay all these associates to do work that they only capture a percentage of. And then the associates is terrible work because like 1 out of 10 of them will actually make partner. And the job dissatisfaction is extraordinarily high because the work is not that enjoyable. And when I started ironclad, even though it was early days and totally unproven, the amount of work attorneys that I had reach out to me and be like, I will take 40% of my pay to just like come work for you because I want to do something else was extraordinary. I think what's going to happen is partners are going to be able to capture more value through AI and they're going to, instead of asking the associate to write up a memo about risks and edits that they might make on a certain transaction, the AI can write the memo. And maybe what can actually happen is the associate can supervise the AI that writes the memo and the associate can run 10 of those different tasks and supervise 10 of those different tasks at the same time. And so you have one associate doing a lot more work, getting more closely mentored by the partner. This is one of the reasons the job satisfaction is so low, is like you don't actually interact with the partner a lot. Like maybe 10 minutes of your 14 hour day is getting some learning from the partner. I think you can have one associate mapped or a couple associates mapped more closely to the partner. Partner can capture more of the hours and work on more clients and the associates can have better, more direct connection to the partner. This is going to mean there's less associates, but those associates don't really want to be in those jobs anyways. At least the ones that aren't on the partner track. And I think what they can have is more interesting. Variety in legal jobs, types of roles. We hired a bunch of lawyers here. We've got lawyers in every single job function here. Like Alex is a lawyer. We've got lawyers on our sales team. We have lawyers that are engineers. I think there's a lot more and their expertise is relevant. I also think there's going to be like a more higher variety of jobs within in house legal departments. You May have, like, someone who went to law school is trained to think like a lawyer working on the custom AI implementation or like the custom clauses that you're getting through your ironclad AI. And I think there's going to be more variety in legal jobs, which is.

Exciting, which we're already seeing. And I can't, like, I echo your sentiment. I can't tell you how many LinkedIn requests I get from lawyers who are like, I want to move into something different from lawyering, but stay within the legal or legal tech and legal AI world. So there's a lot of more opportunity, which is, I think, good for everyone. Going back to what you and I were just talking about on the legal department side and the importance of data and how it can change the way the department is perceived and the work that it does. I actually wrote a blog about this quite recently on why the GC should want to own clm. And it's because of the rich data. Like, the data is gold. Whoever owns that data is going to elevate their position in the C suite because that nuggets of information about decisions and how the company should be run and a lot of folks struggle with CLM is really hard. It touches so many parts of the company. I don't necessarily own all of it, so I don't want to deal with it. And I keep saying, I don't know if you saw the movie, the Breakup with Vince Vaughn and Jen Aniston. There's a scene where she's like, I don't want you to do the dishes, I want you to want to do the dishes. And that's how I feel about the gcs. I want you to want to own this problem. There's so much opportunity, there's so much challenge and winning that you can get if you make this successful. I really want them to step up and say, I know this is ugly across the company and I'm the one who's willing to make it happen and make it successful because they should know what's on the other side of that success.

Yeah. I think that's a really insightful way of thinking about things and I do think this is going to be hard.

Yeah.

Like, we've talked a little bit about this, but I think because there has been a lack of collaboration technology available and legal teams have, in part because of that, been turned into the department of no.

Yeah.

What has happened over time is there basically been shadow legal teams that have been created. Like Deal Desk.

Yes.

Is sort of like doing legal work, but is not supervised by the legal team and is sort of supervised by the sales team. And you know, even in some capacities, like procurement is really kind of like a contract creation process that is in some cases operating in part like a shadow legal team. And I think GCs are going to need to have some tough conversations about reconsolidating those. Like there's very good reasons in some cases why those have been created. The business needed them to be created. But I think in a world in which there's collaboration technology that can make contracting broadly more efficient, faster, more data driven, they need to be reconsolidated or they at least need to be operating on the same platform that's going to put the data in an accessible place and there are going to be some tough organizational and cross functional conversations that need to be had. And I think the most forward thinking GCs and CLOs and legal ops leaders are starting to have those conversations and get collaborative about it. We have some very forward thinking customers who are solving those problems and unique and in interesting ways. And I think that's a great topic of conversation for the community and the legal ops leaders is like, how do we get the business what it needs but also make sure that we have the right contract architecture that needs to be connected and consistent across the company.

Yeah, when I was talking to someone about this recently, they said, well if CLM is making it so easy to access all that rich data and you're going to put AI on top of it, so you can just without a lot of training just ask it a question and get all sorts of insights about the business, what's to stop the CFO or this chief Strategy officer from saying like I want that. I'm going to, I'm going to start querying myself and get all the data kind of away from legal. So and then when I heard that I said, well nothing's going to stop them. And that's why the CLOs and the GCs need to step it up and, and take that role and to step into it and want to own it.

I agree it's going to happen and I think it, it should exist within the legal function because the legal is the function equipped to deal with all of the nuances to contracts, like the risk, the policies, the understanding of like what is being created by a given set of language. But I think if they don't step up other functions well, because the data is that valuable. And so I, I hope that industry gets that right and I hope that, you know, we can help equip legal Leaders to advocate for the right way of this being put together.

Another. It's just reminding me of another interesting conversation you and I had recently with a bunch of senior executive legal ops leaders who, who were all. And this happens, as we were saying earlier, because the role is lonely and it's challenging. You know, every time a group of leaders get together from the legal ops world, we. We really feel this sort of sense of camaraderie. Like, we're all in this together and we're all dealing with these. These challenges of, like, how do we as legal ops professionals get that seat at the leadership table within legal? Like, how do we get the GCS directs to see us as a peer sometimes? Because we're the only non lawyer at the leadership team in the legal department department. And what we had all turned to you and said was, okay, Jason, you know our world really well. You're also the CEO. What are our GCS feeling like? Are they also feeling that they're trying to get, you know, a seat at the leadership team table because they're on the GNA side and people think they're the office of the. No. Like, what is a GC measured on from the CEO perspective? And I loved your answer on this.

Yeah. I think this is really. We're at a really. And that was very insightful for me too, because I think I get to see both sides. The GCs and the close versus the legal ops leaders. And I hadn't really put it together until that conversation that when I talk to the GCs and close, they're like, nailed it. Mission accomplished. Like, I hired a legal ops person. They report directly to me. I love them. And we've, like, kicked off a CLM implementation, you know, plant the flag, mission accomplished type of thing. And the legal ops leaders tend to be thinking like, I'm 2% done here. There's all of these other things we can do. Like, we can wire this up to the finance system. And I think there is a disconnect on knowledge of how far we can go. And I think the legal ops folks can see a lot farther into the future on the systems and data side than the GCs and CLOs are currently thinking.

Yeah.

And it'll be interesting to watch that play out. And I think we can help enable both sides. Really.

It is. I mean, I Counsel so many GCs and CLOs about how to scale their department, what to look for in their first hire, how to build out that role, and I love doing that. So if anyone wants to have those conversations, I'm always happy to, but I think that you nailed it in that once they've gotten over the hump, they've gotten the budget, they got the headcount, they hired the person, they've scoped the role correctly, they're like, yes, I did my part. I hired my legal ops person. Now I can go back to doing other things and move on. Whereas even, I don't know, 13 years after doing legal operations at Google, I was like, oh, my God, I've barely started. We have so much to do. The mountain, we're way at the bottom of the mountain, and there's a little bit of a disconnect there. We were also asking you, how does a GC feel in his or her role? Are they also trying to constantly, like, move up the mountain and feel like they need to establish themselves? And what I think what we asked you was something like, what, how do you judge their performance? Or like, what are you most excited about when this GC or CLO comes to you? Is it, hey, we managed to fix that privacy policy, or we dismiss some sort of litigation threat, or is it we found a new way of working?

Yeah. I think what I hear from the best, most impactful GCs and CLOs is that they want to be business partners. And I think this is where there's really a great partnership developing is Siegel. Ops folks are often come from the business side and are helping the GC and clos show up as a business partner, show up with data, show up with better ways of working. I think that's one of the things I continue to be excited about with the AI that we're seeing our customers use from Ironclad is like, it's faster and better. And that's kind of how the best GCs think about this is like, it's not this false trade off. It used to be a trade off of, like, we're either going to move faster and be more risky, or we're going to move slower and be more safe. And now you can move fast and be safe through technology. And you have to have the legal ops be a part of that technology journey. And you have to honestly follow their lead a little bit because they know how to do this. But I think that that's kind of like the best GCs and CLOs. They want to be business partners, and I think for the first time in decades, they've had the right tooling to actually show up as a business partner.

That's right. That's right.

So it's an exciting time.

Yeah. Okay. So now, as you're thinking about Ironclad, one question that I used to ask folks, even when I was at clock when talking to other founders and CEOs of legal technology, how far do you think you are from the finished product of like where you see where the product could or should be as Ironclad?

So I think I'll answer that in two parts. So with respect to clm, we're there, you know, there is thousands of different use cases, there's AI, there's like workflows, there's like the best security. And I think what's really cool for me is this year I'll be passing 10 years at Ironclad and like we've got the CLM system that I dreamed of literally back in the beginning. That's a really cool feeling. And it's not that like we're not going to keep improving it and like there's a million things we want to work on and like we're really hard on ourselves about what can be better with it.

Yes, there's still a lot, there's a ton I think can be better too.

But I think like in terms of capability, there's not a capability that I'm like, I wish we had that ability to do that use case. What I'm really excited about is kind of what's always been our long term mission, which is thinking less about things from a CLM mindset and more about things from a digital business contract mindset. And we've always been pretty aggressive about this. You know, we have the world's leading Click Wrap technology and Click wrap is basically APIs for doing contracts. So if you click an I agree button, we've actually read the court cases, we've done the compliance to make that legally binding. We'll get you the evidence to show up in court if you want to enforce that agreement button. And there's two companies in the world that do that and we're the best. That is definitely not a CLM capability or it has not historically been a CLM capability. And what we continue to do is think farther out about what is a business, digital business contract need to be.

Yeah.

And you know, I'm excited for some of the stuff that we're going to have coming out this year and beyond that continues to give our customers a full suite of capabilities around the business contract. Some of which are historically thought of as CLM and should be thought of as CLM and some of which are kind of net new beyond the boundaries of what historically has been clm. So that's kind of what I'm excited about.

Do you think there's an end point where we are today? There's clm, there's digital contracting, and there's a lot more that we can do. And, you know, I think I asked you even when I was considering coming here, like, why not jump all the way over? And you've always said very deliberate about what the market is ready for too. Right. Too much change too fast is going to be too much. But you're sort of gradually moving the industry, but also the entire profession in changing the way they work over time. Like, is there. Is there an end?

Yeah. Well, I don't know if there's ever an end, but I think what we continue to be focused on and like, the more I learn about business is it's like, it's actually quite simple. You just need to focus on the customer and solve customer problems. So we're always focused on solving customer problems. We're not necessarily focused on, like a flashy technology. Although if that flashy technology is solving a customer a problem, we're all over it, like AI. I think, like, you know, in terms of futuristic stuff, blockchain's a really good example of. Blockchain is really cool. I'm convinced that someday there is going to be an interesting use case in contracts. Blockchain is not solving any contracting problem right now. It is more of a use case of wanting to use blockchain, which is not a actual customer problem. And I think it'll be interesting to think about, like, how technologies like that fit into and when they are solving real customer problems. And, you know, that's the type of stuff that when there's a meeting of interesting technology and best way to solve a customer problem, we always want to be first to that.

Yeah. And looking across the ecosystem now, the CLM field is extremely saturated. There's a ton of market competition and even new entrants that keep coming, which boggles my mind. Like, it's so saturated. Who in their right mind would want to start a CLM company today? But somehow it's still happening. What advice would you have for the folks that are trying to navigate through all this? This is a question I get all the time. Like, there's so much noise. Like, how do I figure out what's real and what's not? Whether it's AI or just CLM generally.

Yeah, I mean, like, very practically. My advice to people is don't just rely on a demo or marketing. Like, rely on what you're actually doing with your own data by yourself. And I think that continues to be a really easy way to separate signal from noise for CLM companies. Like, you know, if you work with Ironcloud, like we're going to put you in a sandbox before you buy and you're going to be able to test everything with your own data. And that's just a very clarifying function. And so where I see folks misstepping is like they get caught up in some hypey thing, they get a good demo, assume everything works and then they're stuck, left holding the bag afterwards. And that's the thing that just I want to move our industry away from is I think there have been a lot of failed CLM deployments historically obviously like some tough lessons learned by the industry there. And I think there is a world in which we can move away from that and have a lot more higher percentage of CLM implementations be successful. I wish there was more high quality in clm. I think it has been very noisy and very chaotic. Like customers deserve a great set of vendors here and yeah, we're obviously very focused on that.

Yeah. And the PTSD is real. I mean I went through my own failed implementations like many fold of many things. And to go back out to your stakeholders and your leadership team and say like we're going to try this one more time and I think this time it'll be different. It is. It is really rough and it's hard and it's scary and I can see why the GC is like I'm not, I'm not going to own that, make that someone else's problem. But I really think it in the last couple of years we're in a very different spot as an industry and with, you know, ironclad but also other technologies that are out there that are way better than they were a couple of years ago.

It's happening. It's happening.

Yeah. You can be successful. Well Jason, it's been really fun. Such a pleasure. I want to wrap up. We're. We're towards the end of the year. It's December. I'm sure you're a Spotify listener. What. What was your Spotify unwrapped? What came up on your. Like most listened to either podcast or.

You know, I switched to Apple music this year so I'm not super happy with the ui. I may switch back to Spotify but I need to log in and see what my. My unwrapped.

So you don't know trying to think.

I've been listening to a lot of Drake this year.

Yeah, yeah.

Drake on the hip hop front and then Bicep on the electronic music front.

Oh, okay.

That's different.

I don't.

Yeah, there's a Soundcloud, like bicep at Saatchi Gallery that I really like. So a lot of my. If you've read any, like, thing I've written at Ironclad, that's probably been on the background for the past quarter.

Yeah. And people probably don't know there's a huge music culture here at the company. Both of our founders are musicians, so you're like a seasoned dj. Kai, your co founder, is a concert cellist.

Yeah, there's a ton of music culture here. Like, if folks have seen any of our events, like we incorporate DJ Thad, who I think some people might not know is actually on our customer success team and like his full time job is customer success and he does an incredible DJ set.

He's really good. Amazing. Well, thank you again for your time. I know your time is precious, but this was a lot of fun for me personally. And great to have you on the show.

Glad we were able to do it. Yeah. Thanks, Mary. All right.