We’ve all heard about AI’s power to scale many “routine” business functions, but the lawyers are skeptical. In this episode, Kiteworks Chief Legal Officer Camilo Artiga-Purcell describes how his team has used AI to in-source most legal work, including M&A and some litigation. Working with a lean legal team across the globe, Camilo has embraced technology as an essential partner to help his company grow. We talk about how his close and transparent relationships with the board and company leadership gave him the confidence to handle a trial in-house. An unimaginable feat for most in-house departments.

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Small But Mighty: Using AI to Scale Your Legal Department Camilo Artiga-Purcell GC of Kiteworks

My name is Camilo Artiga-Purcell. I’m the general counsel at Kiteworks. A fun fact about me is that I have a Labradoodle named Winston whose best friend is a very small pug named Walter. It’s a fantastic life. I live in Mill Valley.

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On this episode of the show, I’m excited to welcome Camilo Artiga-Purcell, the general counsel of Kiteworks. We are going to talk about being tech-forward, doing more with less, and building trust with your leadership team and board. Camilo got on my radar, actually, through his marketing department, which is super interesting. I got pitched for a lot of guests. I do not normally get those pitches. I’m just giving a shoutout to the Kiteworks marketing team. We are not going to talk about what they want you to talk about, though. We’re going to talk about helping people be more current as a GC. Welcome, thanks for being here.

Thank you, Stacy. I’m at your disposal. I’m very pleased to be here with you this morning.

Were you aware that they were pimping you out to show?

I am aware that they burn the midnight oil and are always working on getting folks on shows and pumping out content on a daily basis.

As I told you when we met, I thought they did a nice job. We’re not going to talk about Kiteworks and everything that they do. I do think it’s important to set the stage for the audience about how big the company is. Where are you? How big is the team? What is your portfolio?

At this point, we’re between, I’d say, 550 and 600 employees. The headquarters is in Silicon Valley in San Mateo, California. We have offices in New Hampshire. We have an office in Singapore. We have various offices across Europe, spanning from Zurich, Switzerland, to Amsterdam, Romania, and Bulgaria. Basically, Europe, Asia, and the United States are growing quickly. We just welcomed a company into the fold. Actually, it was announced two days ago. A company called WAMNET, which is the newest member of Kiteworks, and that’s out of Tokyo. We have a new Tokyo office, which is very exciting. Lots of happening.

A global company.

Indeed. In terms of the size of the company and the economics, I do not want to get too specific, but we’re in the 200 million band of ARR. Kiteworks is a cybersecurity company, plain and simple. The upshot is we license what’s called a private data network built around a data policy engine and control plane. In plain English, it gives you one place to set and enforce data governance policies so that, in essence, you have control over every stripe of data that sits in the company and that moves in the company and outside the company.

The exciting development that’s launched this year is taking the existing tools we have. Our engineers have been hard at work developing analogous technology to govern AI agents, which is becoming, as we’ve seen, increasingly important to get these agents under control so they do what you want them to do and nothing more.

Let’s talk about your team. This is my gleaning from how you described the company, you need to be a trusted company, right? You’re saying you’re part of data governance and cybersecurity. Trust needs to be, I would bet, an important attribute of your company. The legal department is usually a big partner, a big source in that. Talk about, you’re in, again, a global, growing company. Where are your lawyers? How big is your team? How are you keeping that going?

Building a Lean, Tech-Forward Legal Team

We’re an incredibly lean team and at this point intend to keep it lean. In terms of full-time, we have fourteen members. I’m the general counsel for the company. We have another general counsel who covers Europe. He sits in the Amsterdam office in San Mateo. I have a fantastic contracts manager who works with me. We have another lawyer who sits in our Germany office.

Collectively, we cover the globe. In terms of the day-to-day, the two more junior lawyers handle vendor contracts, customer contracts, and various things that come in, and then the two GCs handle strategic affairs. We do get in the trenches when we need to as well. We’re heavily invested in our time in handling M&A litigation. On the litigation front, it’s handled domestically and internationally because you’re in various jurisdictions.

That would be a bit reckless. We do engage outside lawyers. As needed, we supplement. We’ve got, for example, in the US, a small boutique firm on retainer. They handle any spillover work to the extent we need it. Of course, we have the traditional model, the proverbial white shoe outside firm, only on an as-needed basis to do, in essence, consulting work. On the very large deals or very large litigation, we’ll tap them, but only on an as-needed basis. The idea is to do more with less.

This is where I really want to dive in because you said litigation in-house. You glossed over that. We’re going to, I’m going to tease that you did a very unusual thing in-house, litigation-wise. I’m teasing that we’re going to get into that a little bit later. This is a growing business. You have an extremely lean team. It’s growing. You’ve got to get sales, commercial contracts, all that. You teased at the beginning.

You just completed an acquisition. You’re not using a lot of outside counsel. This is why I wanted to talk to you, because everyone is talking about the promise of AI, tools, and less reliance on outside counsel. It sounds like you use outside counsel really just in a sprinkling, not really shoulder to shoulder with you. Tell us about how you’re supporting this business with four lawyers.

Very early on, I would say by Q4 of last year, and then with a full-court press in Q1 of this year, across every discipline in the company, there has been a mandate to identify work streams and critically identify where we can become more efficient and leverage AI. We took that very seriously. My view is that across corporate America and internationally, the joke is always that accounting and legal are always the last to catch up technologically, that we’re all dinosaurs and we prefer to dust off our large tomes and go to the paper page.

Slashing Contract Cycles With Custom AI Playbooks

We took it as a challenge, and we variously sat down seriously, whiteboarded the different processes, and then started playing with agents. In our case, we leveraged Claude. For example, I’ll give you an example because I think it makes it more real. We looked at. Here’s our standard EULA, and here are the most heavily negotiated contracts we’ve done across various industries, pharma, banking, healthcare, education, etc. What are the issues that have recurred? We mapped. This is our starting point. These are the issues that keep coming up.

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This is where we give where there’s wiggle room, and these are the few red lines. We did that across the team and across the contracts and then created an agent that has our rules. We, in essence, took four brains across multiple negotiations and created a toolkit, and the agent only operates on that toolkit. Now, every time a third-party contract comes in, whoever on the team is handling the contract has the benefit of all of our collective knowledge, has the playbook, and runs it. Instead of taking half a day, combing through a 40-page license agreement, you have a redline in one to five minutes.

The exercise is that we’re still reading every word, and you still have to make sure that the agent correctly applied the playbook, but you’re cutting down the start-to-finish time to get it back to the potential customer or to the vendor. You send it back the same day. If you do not send it back the same day, there’d better be a good reason because there’s no justification for it.

In terms of the cycles, instead of it taking three weeks, a month and a half, six months, at least on our side, we’re cutting the time down. I would say 80% on a contract-by-contract basis. Now it takes two to tango. I’m not saying every deal gets closed 80% faster because our counterparties are not all doing the same thing, but it’s going in that direction. You extrapolate, and the same process we applied for contract negotiation, we apply it more generally across the board. That’s the idea.

I want to ask about the process of getting the brains together because lawyers are pretty independent, and I think we are also in-house. You’re just dealing with a lot of inbounds, a lot of in-the-moment work. Taking the time to sit down and put those collective brains together, like you had to really prioritize that, and I would imagine defending that against a bunch of other business people and all those inbound, that inbound demand.

Treating AI Playbooks as Living Roadmaps

There hasn’t been. In terms of our department putting together the various playbooks, that part’s easy. We have a regular cadence. Every two weeks, the whole team sits down for an hour or more, whatever we need, and discusses all the pertinent issues of the day. This was critically important to us, so important that we could actually be in person. We met in Santa Monica at the beginning of the year, two lawyers from California, our Dutch colleague, and our German colleague, and we sat down for a couple of hours, and we mapped out the roadmap for the year.

We obviously prioritized AI, and then we’ve had a number of working sessions thereafter to fine-tune it. I’m not suggesting that you sit down, map out the legal playbook in the example I gave for customer contracts, and it’s good. You do not touch it. It’s constant iteration. Every time we get a new bespoke contract, something invariably comes up. There’s another issue, another way of looking at it. We iterate, and we update the playbook. That’s how it’s going.

It’s not a set-it-and-forget-it.

Absolutely not. I do not think it can work that way because we have to have enough humility to realize that it’s a work in progress, and it will need fine-tuning.

When we spoke, you were talking about the value that you’re getting out of what you call the Claude and Claudettes, the agents. You also teased that you were doing a big M&A deal with the support of AI and not using outside counsel. Is that in fact what you did?

It is. That one is ongoing. I cannot discuss it in detail. What we have done is that the architecture of the deal has pivoted. Since we last spoke, actually, this highlights something important when dealing with AI. Understanding where you can use it aggressively and also knowing the shortcomings. In this particular example, we planned initially under the term sheet to architect the deal under a share purchase agreement. For specific issues we do not need to get into, the architecture has shifted. We’re now using the structure of a reverse triangular merger. No one on our team in the past has done a reverse triangular merger.

I do not even know what that is, by the way. It feels like a chess move.

You get to the same place the way you get to the same place in terms of a traditional acquisition, versus how it has to do with how you get the consents to sign off on the deal. You back into it and you deal with issues on the back end, post-close. The other is a done deal out of the gate. The upshot, back to your question, is that we’ve done 6 or 7 acquisitions using the SPA. We’re very comfortable, and we have, historically, we have used highly sophisticated outside counsel.

We have the model, and we’re very comfortable with it. When it pivoted to the reverse triangular merger, could we have said, “Fable is fantastic. Will we just plug it into Fable”? Hypothetically, yes, we wouldn’t be aware of the blind spots. I was not comfortable that we’d have the sophistication and the deep knowledge to question Fable and identify spots where it’s right, where it’s wrong, and where we need to probe further. Because of that, we did tap outside counsel to handle what I’d call the architecture of the deal. On the due diligence side, we are still doing that in-house.

Let’s talk about how you’re approaching due diligence in-house with four lawyers.

You say four lawyers. The reality is I have thousands o what, I would call junior to mid-level associates, depending on the task.

Let’s talk about them.

Accelerating M&A Due Diligence Without Big Law Costs

I look at it similarly to the way I’d look at discovery in litigation. You have a massive one, or this is a small to mid-sized deal. The VDR, the data room, is not gargantuan. There’s quite a bit of duplication. Take employment contracts. Once you’ve seen one, they basically follow the same model. There are a few variables that change. Historically, you’d have a junior lawyer, usually an outside junior lawyer, billing you 500 to 800 plus an hour reading through all of these agreements. That’s hugely inefficient. Any incremental upside value just does not justify the spend.

What we’re able to do is, because it’s M&A, in my view, it’s justified to use one of the more rigorous models. Opus 5 or Fable, depending on the task, given we’re using Claude. You map out precisely what you’re looking for and feed in a highly detailed prompt. The trick is that you do not just run the prompt. You make Claude regurgitate what you’re asking it and have it propose a highly detailed prompt. You go back and forth and back and forth and iterate.

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Finally, when you’re good with the prompt, you have it run a full analysis on the data. That’s not the end of the exercise. What it generates is, in essence, a highly detailed checklist where you’re able to go and home in on the documents that actually matter. In essence, you’re using it to issue spots and allocate your time in a very targeted way. You’re looking at the documents that matter. From that, you end up generating your red flag report.

You end up being able to very easily take the red flag report, plug it into Fable, and have Fable update the DRL. Meaning the working spreadsheet that both sides are using to address where we have checked off issues, where we need to probe more, get more documentation so we’re satisfied, where there are gaps, and identify where we need to strengthen the reps and warranties so that the buyer feels comfortable.

Can I ask you, it sounds great, to the point of the risk tolerance and again, the trust that your leadership team and your board is putting in you. How are you getting comfortable? What are the guardrails? What’s your QC process like? If you were working with a second-year associate, you would be talking to that person. You would be reviewing their summaries. You’d even be in the data room saying, “I know you did not look at the severance,” whatever. How are you accomplishing QC or supervision of your Claude and Claudette here?

Establishing Quality Control Guardrails for In-House AI

It’s a very fair question. In this example, what we have is a detailed sheet that, at random, has a delegated task. A human being is doing it across each of the vectors. In this case, you’re looking at IP. You’re looking at employment agreements. You’re looking at customer contracts, tax, etc. For each of the components of the VDR, at random, you’re going in, and you’re checking. There’s the deep dive where a human being is actually reviewing documents based on the initial scan by Fable. On top of that, the QC is going to check that what it says actually pans out.

Are we looking at every single document? No. Are we vetting every single assertion? No, you’re doing it where statistically you can sort out whether we’re 95-plus percent confident that it’s accurate? If the answer is yes, in terms of our risk tolerance, this whole process will cost in tokens when we’re all done, probably somewhere in the order of $3,000 to $7,000, plus the time of the individuals. We’re expensive people. Historically, the spend on outside counsel, even for a deal, a small to midsize deal that we’re doing, easily the legal due diligence alone is somewhere in the order of half a million to 700,000.

Let me ask, where are you having a conversation with your CEO or whoever’s running the business part of the deal? “I could hire this firm to do this. Our team has built these agents. We’re using Fable.” Are you being transparent with the business team that you’re foregoing? What would normally be an insurance policy for the general counsel?

We are locked in at the hip. It’s funny you ask. It’s the other way around. It’s from the CEO and the board saying, “You have to leverage these technologies. You have to identify inefficiencies, get out of your comfort zone, and push forward.” That’s precisely what we’re doing. Nothing happens in a vacuum at Kyrox. One of the luxuries of being a company that’s growing, but still 500 to 600 people, we’re not so big that anyone’s inaccessible. I have the luxury of walking two offices down, and Jonathan and I, the CEO and I, are chatting.

I walk twenty more steps, and I meet Tor, the head of M&A, and I am chatting. This is a true partnership and dialogue between and among the various departments. All of us are laser-focused on identifying how we can become more efficient. I think that acting from inertia or acting from fear of “If I miss this one thing, it’s going to be catastrophic, and I’m losing my job.” That’s backwards thinking. It has to be.

Can I just say, though, in a tech startup, you might have, we hear a lot from Silicon Valley, there’s a lot of failure fast, all that stuff. In more established businesses, in highly regulated businesses, in public companies. Some of those external things, like, I’m in healthcare. I’ve got more than 50 agencies that are overseeing our business. We’re making sure people live and die. You do not live or die when they’re in our care. It feels a little bit like a different conversation with leadership about relying on emerging tools.

I would respectfully challenge that. Kiteworks is not a startup. We’ve been around for an excess of twenty years. This is not a VC-backed company. This is majority-owned by the existing employees and past employees. We deal with highly regulated businesses, but historically, what you’re describing is passing the buck. It’s not that the risk goes away. It’s that Skadden will take the risk for me, Pillsbury will take the risk for me, and HSF Kramer will take the risk for me. We do not accept that because what happens is that it becomes a blank check. You’re not just the reason they can justify $1,400 an hour is not just the work product.

Moving Past Outside Counsel as an Insurance Policy

It’s that we’re absolving you of risk. Our view is that we do not want to pass the buck. We want to be very conscientious about what the risk is. We want the buck to stop with us. Because we take that approach, the silver lining, which I think is material, is that you actually become a more efficient business. You save a whole lot of money that can be reallocated to other things that make the product better, that make the product more secure. I agree with you. If there is a problem, it falls on my shoulders. It falls on the CEO’s shoulders. We wouldn’t have it any other way.

I get the framing of passing the buck. As you were talking, I was thinking, those legal fees, it’s almost like an insurance premium. I do think our culture is now evolving around what it is, because the legal fees have gotten so high. When you said $1,400, that sounded like a bargain to me. I’m seeing a lot of $1,822 an hour, and law firms sometimes make things too expensive. My favorite expression. Pigs get fed. Hogs get slaughtered.

It does look like that insurance is putting the risk really in sharp focus for the GC. I want to talk about being joined at the hip, and about transparency and those conversations you might be having. They’re expecting you to leverage tools to be more efficient. Just for this deal, as an example, this diligence project, did you say like, “We could use Skadden or whoever that’s going to be half a million dollars, probably minimum, or me and my team can do it with Fable and it’ll probably be under 10,000.” Do you have that kind of conversation where they just say, “Camilo, you run, and we understand you’re going to use tools”?

Before we kick off a deal, there’s a board-level discussion, then there’s a C-suite-level discussion looping in the relevant team members who are going to be working on the deal. We map in the same discussion where we’re mapping what’s palatable in the term sheet. We’re also gaming out what the workstreams are and what the cost is. What are the different consultants we might retain? Where can we do it in-house? It’s a totally transparent discussion. Down to the T of what’s the budget we can stomach given the deal size.

It’s all based on everything we’re doing has to be rationed to, in this case, the purchase price. None of this happens in a vacuum. I hope this is not unique. This should be the norm. There’s total transparency. There’s no culture of you doing it in your silo, so if something goes wrong, we just drop the axe and replace you, and it goes away. That’s not what this is at all. It’s total transparency. It has to happen that way because the legal due diligence does not happen in isolation from the security due diligence. Amit, the head of M&A, is intimately familiar with and involved in the contract negotiations.

Why? It’s because we’re embedding deal terms into the contract. It’s not a purely legal exercise. Again, we’re able to be nimble because we’re a mid-sized company and we’re private. That’s where we sit. I will say that I do not want to totally prove your point about risk. When you’re a publicly traded company, when you’re in certain disciplines, I understand why, at least historically, there’s been an impulse to always hire consultants, law firms, and pay them a lot of money as an insurance policy. We need to challenge ourselves, whether we’re in a private company or a public company, whether we’re regulated or unregulated.

Obviously, the risk assessment changes depending on those very important variables. I do not accept that just because it’s been done a certain way, we need to continue doing it that way. One of the problems for corporate counsel internationally, in particular in the US, where the fee structures are just so out of proportion, it’s become a chicken-and-egg scenario. We allow ourselves to pay these gargantuan fees because that’s just how it’s done. Invariably, the business model does not change. It’s this very bizarre model by the hour, where the incentive is the customer, the client.

The company in this case is totally at odds with the incentive of the outside counsel. I’m not suggesting that there’s anything pernicious happening. Incentives matter. There needs to be a total recalibration. I’m not saying outside counsel is not going to get paid a ton of money. I’m happy to pay $10,000 for 30 minutes of the right senior partner’s time if I get advice that makes economic sense.

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In the current environment, whether we like it or not, whether outside counsel likes it or not, it’s going to change. Change in a way that’s much more palatable for both sides and intentional about it versus just reacting to it. I also think from the client’s standpoint, it will be much more secure, and there will be fewer accidental breaches of privilege if both sides are intentional about using AI responsibly. It has to happen now. I do not think it can wait a year. I do not think it can wait a month. We’re in it.

Let’s talk about you’re not wrong. You’re right on the money that we’ve got to adapt. We’ve got to become more tech-forward. As we’re getting on, I shared that someone sent me a job hosting this week, and the CEO wants a tech-forward GC. Have you always been tech-forward? How have you gotten yourself immersed in and fluent in this technology?

First of all, I appreciate the compliment. I am far from fluent. I suppose will date me. When I began in the practice of law, our firm was using WordPerfect.

I’ve been there.

We had a large library I would go to. Spent more hours than I care to admit at 1:00 AM in the library sifting through case law.

I’ve manually Shepardized. Talk about a real good use of time.

I certainly wouldn’t say I’ve always been tech-forward. It’s a very steep learning curve. At times, it was not easy. I would say two years ago, plus Tim Freestone, our head of marketing, was very adamant that we were on the cusp of an AI revolution. You’ve got to get on board. You have to get very familiar with this. We need to be leaders. Candidly, I thought it was an interesting read. I’ll move on to the next article in the Financial Times or the Wall Street Journal.

I was wrong. I regret not diving in two-plus years ago. That does not really matter. Once you have the a-ha moment, everyone, I think, who engages with this will have the a-ha moment very early on. “I was able to spend more time on strategic thinking and analytical thought. I spent a fraction of the time on the meat and potatoes.” That’s just the tactical part of the job. Once you have the a-ha moment, it actually becomes exciting.

For lawyers, it’s actually easier because, by nature, we tend to be creative, intellectually curious human beings. It’s actually a lot of fun. If you look at it like a puzzle, you identify that this is the work stream, this is the deliverable I need to get done. You start playing with this very powerful tool that helps you achieve it. Maybe I’m a nerd. It’s fantastic. It’s very stimulating to the mind to engage with these tools.

Every journey begins with a single step. It sounds like many of us, as you said at the outset, accountants and lawyers, are late to the party a lot of times when it comes to making changes. You’re there. Based on our prior conversation in this one, I think you’re really a leader in this. I teased it early at the outset. You blew my mind when we met because you’ve done something that I do not know I’ve heard of other in-house GCs doing, which is that you try the case completely in-house. You’ve got to tell the story. I also want to talk again, as part of that talk, about how to have that risk conversation with your leadership and your board, and why they were comfortable betting on you to carry the weight in the courtroom.

Defending Multi-Million Dollar Litigation In-House

The background is important. I’m a trial lawyer by trade, which is a little unique for someone in the general counsel seat. Especially at our size, the GCs tend to have IP or M&A experience. I was a bit unique. It’s not as though I came in blind. This is what I historically did. It was simple. This was an insurance subrogation case that you did in Santa Clara County, so in our backyard. The total risk was somewhere in the ballpark of $4.4 million.

I did the internal risk assessment, and we felt very confident that the plaintiff was wrong and that, ultimately, as unfortunately happens more than it should, it becomes a shakedown. They know the defense costs, and if you’re going to retain outside counsel in a case with a 4.4 million liability. The playbook says to go mediate, write them a check, and move on. We do not operate that way at a high level, because I do not want to get into all our litigation strategy at a high level, if we determine. We do a robust analysis of the claims out of the gate, regardless of the jurisdiction.

Are you using AI for that, or just from your prior litigation experience? In California, for people who do not know, we have this really onerous broad statute called 17200, which is an unfair business practice. Every contract case and even some negligence cases will have 17200 cases. It is a catch-all, and it is bulls***. It is one of the drivers of the typical resolution model.

Predictably, 17200 was alleged and ultimately dismissed in this case. It survived all the way through. I was trying. At the time, I did not use AI because this case began in, I want to say, ballpark 2021. I was not in the library.

You’re still on the sidelines then.

I wasn’t in the library. I leveraged a Lexus tool. We did a full analysis, and we believed that we had a high likelihood of success. Not just a legal analysis. We also pulled in what became the discovery in the case from our side. We pegged the risk as quite low. We tried it. That was the decision we made. I can tell you that when we’ve had larger cases, and we have one ongoing now, a large class action. We do use highly sophisticated outside counsel. We litigate all cases in-house.

It’s a rigorous analysis of what the value of the dispute is. What are we looking at? What are the merits? The merits matter. If we believe fervently that we’re right on the merits and that the documentation critically backs that up, and we have, let’s call it, an 80-plus percent chance of prevailing on the merits. We will try that case every time.

You’re in-house, though. You’re the GC. Your office is two doors down from the CEO. I’m guessing there’s a pretty well-worn flight path between your offices. You’re doing global business. How do you have the time to defend a lawsuit in-house, respond to the discovery, take the depositions, going to the court hearings? That is what is the mindblower to me.

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It’s budgeting time. The reality is, at least in California, whether you’re in the federal courts or the state courts, the life cycle of a case today is called five years. That’s just to get through the trial. You’ve got the whole appeal process. It’s a calamity. There are obviously court funding issues. There are a number of issues. That’s a different podcast in and of itself. Because it takes so long, if you’re intentional about it, you can stage it. We were very intentional about staging, discovery, motion practice, depositions.

It does not fall towards the end of the quarter. When we’re in the midst of intense M&A, we’re able to kick the can down the road. My view is thyou fight hard within the painted lines. I’m a big believer in litigation in maintaining communication lines and respect with opposing counsel, no matter how hard you’re fighting or how much the parties disagree. When you’re able to create those sorts of relationships, even in tough cases, I find that the parties are very reasonable and you schedule around each other. That part’s not hard.

You work the calendar like you’re writing motions, like you talked about in summary judgment mode. I cannot imagine having the time to do that. You said in 2021, you discovered the new world of the army of agents for you.

I may be an in-house lawyer. I was not always an in-house lawyer. I am not shy, and I do not mind being at my computer at 11:00 at night. Having a little Tchaikovsky playing in the background and go through the exercise. I actually find it to be intellectually stimulating, and it’s fun in that, as a litigator, there’s nothing that ever approaches being on your toes, arguing in open court, trying a case. It’s fun. It’s especially fun when you get a good result.

Talk about, again, back to that risk matrix that I’m thinking about, again, do you go into the CEO’s office and you’re like, “Listen, if you want to pay a million and a half, I’ll spend a day in a mediator’s office, and we can get this off the plate. The case is bogus, and we’re going to win, or at least I’ll save us on the legal.” How did you approach the conversation about, “I’m going to do this”?

There was not one conversation. There were a multitude of conversations. We both find it intellectually stimulating. It’s total transparency. Again, this is not something I have to sell. In terms of the way we view risk and the way we view litigation, we’re totally aligned. He’s the one who brought me into Kiteworks in part because we see the world the same way on these issues. It’s total transparency. I do not have to push anything. It’s a total conversation. We do not always agree, but it’s a dialogue. There’s give and take. It’s all done openly.

There are no hidden agendas. This is from the board all the way down. There’s total transparency. At the end of the day, in terms of litigation, we’re not dealing with criminal cases. We’re not dealing with life and death. What we’re dealing with, as crass as it sounds, is money. When you’re dealing with money, as the GC or anyone operating in the legal department, you cannot divorce the business reality and get so embedded in the legal theory and how it’s going to pan out that way?

It always has to come back to what is at risk and what are the probabilities? What’s the likelihood of success? Once you can pinpoint those with some accuracy, then you can make a rational decision about whether I need to go out and bring in the Norton firm, or do I do it in-house? Do I maybe go out and get a solo practitioner or a very small boutique to give me support at 30% of the cost? These are the discussions we’re having, and that’s how we execute the litigation strategy.

Tell me the punchline. What happened with the trial that you handled yourself?

In that trial, we were sued for 4.4 million. Technically, we lost a $44,000 judgment. I thought that was going to be the end of it. They’ve now appealed. We will cross it to PLM. If we have this podcast in a year and a half, I will tell you we had a total victory, and we recovered all our costs, to be continued.

For your business, as you were talking about the M&A meetings and how you’re framing up legal, how much to spend on legal fees? I would imagine that financial calculus was something that you had conversations about. It costs a fortune to defend even a $4.4 million case, even if you’re using a smaller firm.

At some point, the legal burn is divorced. If you do it the traditional way is divorced from the cost of the potential liability. Even with a boutique, you’re looking at getting all the way through trial easily a million.

Totally. Again, that was the hook for me. I’ve learned a lot from Camilo. As I’m thinking about our team, I love the whiteboarding. I love thinking about taking a step back and looking at what we can do more efficiently and use today’s really powerful tools. I close all episodes with a lighter conversation. I’m very intrigued to hear what your pump-up song is.

Pump-up song during the week, I would say, especially if I’m a little groggy, I’ll listen to Bon Jovi’s Have a Nice Day. That usually gets you roaring on all cylinders.

Thanks for being here.

Thank you, Stacy. My pleasure. Bye-bye.

It was great.

  

Important Links

• Camilo Artiga-Purcell on LinkedIn
• Kiteworks
• Tim Freestone on LinkedIn
• Certified Corporate Governance Professional
• The New Rules of Executive Presence

  

About Camilo Artiga-Purcell

Camilo Artiga-Purcell serves as General Counsel at Kiteworks, where he leads legal strategy and governance initiatives for secure content communications and collaboration. With extensive experience in data privacy, cybersecurity, and emerging technology law, he advises organizations on managing AI-related risks while maintaining competitive advantage.