Ben Chiriboga | How the Evolution of Technology Is Changing Legal

Elise Holtzman: Hi, everyone. It's Elise Holtzman here, a former practicing lawyer and the host of The Lawyer's Edge Podcast, where I sit down with successful attorneys, legal marketing specialists, business leaders, and authors to talk about how lawyers and law firms can grow and sustain healthy, profitable businesses.

Hi everyone. It's Elise Holtzman here, and I'm back with another episode of the Lawyer's Edge Podcast. Today's episode is brought to you by the Ignite Women's Business Development Accelerator, a nine-month business development program created by women lawyers for women lawyers. Ignite is a carefully designed business development program containing content, coaching, and a community of like-minded women who are committed to becoming rainmakers and supporting the retention and advancement of other women in the profession. Registration is now open for the 2025 Ignite cohort and early bird pricing is available. To learn more about Ignite, visit thelawyersedge.com/ignite.

I am really excited to welcome my very fun, very entertaining guest today, Ben Chiriboga, who is the Chief Growth Officer at Nexl. Ben left the law firm Lawyer track at the young age of 30. He figured it out and he set out on a journey to find his place in legal, eventually finding his place in legal tech. Today, he helps grow Nexl, which is a legal tech company that helps law firms grow by uniting marketers, business development, and lawyers all on one platform. He creates content about the changing nature of legal culture through his newsletter, This Legal Life Newsletter. Ben, welcome to The Lawyer's Edge.

Ben Chiriboga: Thank you so much. It's fantastic to be here. I am really looking forward to the conversation. You and I always have the best time together, so let's get into it. Open book, let's talk.

Elise Holtzman: Okay, I like the open book part, and you are so right. We have so much fun together. We had the chance to meet in person for the first time at the Legal Marketing Association Conference in Boston a few months ago and I found out that not only are you smart and driven and have great ideas, but you are hilariously funny so I really enjoyed our time together.

Let's start out with your legal journey. How did you wind up going to law school in the first place? What did you think you were going to be doing with a law degree when you first got into it?

Ben Chiriboga: Like so many lawyers and people who go to law school, I think, I had no idea what I was going to do after I graduated undergrad. I was a double major in biology and art history. That's because I really like evolution and also art history was just where all the cool people were. I feel like it was just interesting. I liked this balance.

But of course, I wasn't smart enough to be a scientist and art history, even though it's great for coffee talk, it's hard to make a career out of even though I use it a lot now though and I'm married to an artist now so that always came in handy. I looked at the time I was really thinking about what's the area that I can combine these two things while still having a profession.

My mom's a nurse, my dad is an engineer and so naturally without any lawyer in the family, I was pushed to go to law school for one reason or another. So I found myself in law school going through that. Now, as you mentioned, and we'll get to, as you mentioned in the thing, that eventually changed. In fact, I had a big evolution of my legal career over the last 20-something years. I do love evolution. I thought I was going to be a scientist at some point, but I've seen a lot of evolution in my own legal career. That's how I ended up as a lawyer, graduating in 2009.

Elise Holtzman: What did you do when you first graduated from law school? Did you work in a law firm?

Ben Chiriboga: Yes, I'm from Miami, Florida originally, and I was going to school in the Northeast. I had gone through many winters and I decided, “You know what? I think it's time to go back to the sunny shores of Miami.” Now cue in 80s music, a little bit of Miami Vice, and just imagine me back and being a Miami lawyer and all of the cliches are true. I went to the office just wearing a tank top every single day. It was nothing, but it was like Grand Theft Auto. No, I'm completely kidding.

I ended up getting a job being a maritime lawyer. People love that because they meet very few maritime lawyers. But of course, maritime law is very large here in Miami, where I'm recording today. It was a fantastic chance to dive into that world. Practiced for about six and a half years as a maritime lawyer, specifically a litigator. I think I learned so much about the application of really, psychology, about telling great stories, about what it means to put on convincing cases based on fact and logic and emotion that have gone on to serve me really well.

But just like other first-year associates, I also learned a lot about some of the confines and the constraints about being within the law firm environment that eventually led me to make a big decision sometime around my 30s.

Elise Holtzman: What was the decision? Was the decision just “I'm leaving, I'm not doing this anymore, but I don't know what I'm doing in the future,” or were you going to something specifically?

Ben Chiriboga: So this is around 2014-2015. I was a senior associate at the time, really running discovery. Shout out to all my senior associates there, knee-deep in paperwork. But 2014, 2015 is a really interesting time specifically within technology because for the first time, there's early artificial intelligence that is coming out specifically with an application around e-discovery for some reason.

I'm working in a boutique firm and we bring in an e-discovery provider to really help us with some e-discovery, and like a flash in the light coming to God moment as you were, I all of a sudden saw this confluence of e-discovery technology, specific type of technology, which is this early artificial intelligence natural language processing that can read text and then understand semantic understanding of text and then turn it over.

What it ended up doing in a practical way is helping us find this needle in the haystack. But I saw it as really this weird watershed moment that, wow, practice and technology are really going to come together. Once I saw that, I really couldn't unsee it. It was in my background. I went another year practicing and I never lost this idea. In fact, I had a very specific voice in my head, which was my grandfather.

My grandfather was a successful entrepreneur in South America and he started a bunch of businesses. He would do a lot of import, exports. He would travel with my dad and my uncles and my aunt and they would go to different places and he would import things that he saw in other places into South America. This is in the 60s, 70s of South America so there's a lot. They would travel to New York and they would see via the pull-down things that people put in front of storefronts as like security.

At some point in time, American cigarettes, a bunch of different things that they were always importing. He always left me with the lesson that if you want to be successful, you can be the smartest person in the room, the hardest working person in the room, or the first into something that's happening. He always tried to be the first, hence the import, export.

When I looked around at the law firm, I said, “Well, I already worked pretty hard. I'm already working like 12 hours a day. I'm going out working during the day, going out at night in Miami. It was very fun in my 20s. I'm definitely not the smartest person even in this law firm. So, okay, that might be a problem.”

But I did seem to be one of the only people within that law firm that was seeing this as a bigger moment besides just winning a case in the short term by using some technology that some guy came in, some vendor came in and did it and it was gone and nobody was talking about it. I seemed to be the only one that was struck with it.

I heard my grandfather's voice in my head and I said, "Wow, let's see." So at 30, I took a two-week vacation to Thailand, had an eat, pray, love moment for myself, came back and all rejuvenated and very Julia Roberts-y walked in and said, "I'm starting a new life." That's when I moved up to New York and decided to get into legal technology.

Elise Holtzman: Curious about something, Ben, because I work with a set of personality tools that I use in my coaching practice and people who listen to the podcast will know that I talk about it sometimes. Research shows that lawyers tend to show up, not all of them, obviously, but a majority, a pretty large majority of lawyers tend to show up fairly similarly because we self-select into law school for a variety of reasons.

We tend to be linear thinkers, and we tend to think more inside the box than outside of the box. In talking to you, it has struck me that you don't fall into that category of most lawyers. We talk about nurture and nature. We had the nurture from your grandfather telling you to think about things in a different way and be first to market if you could.

But I'm wondering how you view yourself. Do you view yourself as a risk-taker and a visionary? Because it sounds to me that that's what you're describing but obviously, you know yourself best. How do you see yourself as similar to or different from most lawyers in terms of perspective and thinking?

Ben Chiriboga: Yeah, so culturally my father's from South America and so I have a big Hispanic part of myself. My mom is from Western Pennsylvania. How they got together, I mean I don't even know how they understood each other. This was 1976 University of Pittsburgh, but I've always seen myself as a person who can connect two disparate things between each other. I've been able to live my life half Hispanic, half American, half small town, Western Pennsylvania upbringing, Irish, German kind of thing with Spanish and all of this.

I grew up in Miami, which is of course, very multicultural. I've always seen myself as somebody who can try to connect the dots and try to see from other people's perspectives. When I went to undergrad, I didn't just pick one major or the other. In fact, I was interested in how do genes of biology affect the memes of culture in art and art history. I'm always interested in these kinds of questions.

Whenever I came to law practice, while I really respected the idea of precedent and really appreciated the idea that this is how we do things and this is how things are done, there's absolutely room for precedent, there's also, just to use a fancy word here, the dialectic of what isn’t precedent and basically the relationship between two things constantly.

In real life, of course, there's not one way to do things. The opposite of a good idea is typically another good idea. What's really interesting is the relationship between these two ideas. That's really how I see myself. I'm married to an artist, and great creativity comes from basically mixing two very understood things, but mixing it into one. I think that that's what innovation is.

What I tried to do is I always try to bring in a new element into a way of doing things, just to see what happens when you mix one thing with another, like cooking, something like that, and bringing things in, trying to always make the recipe a little bit more interesting in the process. That's what I see myself. As a visionary, I don't know, but I do see myself as a cook and I like to cook it up.

Elise Holtzman: Tell me about cooking it up in legal tech. How did you get started in legal tech and how did that lead you to where you are now?

Ben Chiriboga: So the year is 2016, I landed in New York. I have about $60,000 in my pocket. I mean, it was a fun time in Miami. I was making good money as an associate. I landed there in New York. I know that I want to get into legal tech, but I really have no network, no idea what I'm going to do, how my skills are going to transfer from being a maritime lawyer into legal tech.

Over the course of two years, and really just putting down money and trying and failing, starting my own companies, all of this, I really come to understand that legal technology is one part understanding the business of technology and the business models and marketing and sales and CS and all of that. That's like the tech side of legal tech if you're going to run a business per se. But then the other part is of course legal acumen and just understanding legal culture. Legal culture is very, very, very specific.

Over the course of the next two years, I started to marry again and try to connect these two things into something very specific for myself. Where I landed was, how do you help early-stage companies, early-stage tech companies in legal tech, really go to market, and actually make an impact or grow, scale, sell, service, and all of those things, all of those things together really, the combination of marketing sales, CS, all of that together for delivering really value.

That's where I made my place. I decided to go deep in early-stage technology companies. Like $0 to $10-million companies who were trying to bring an innovative product basically to market. That's where I really found myself. Life, of course, is a lot about what you can control, which is “This is what I'm going to do, this is the value that I'm going to bring, this is my particular perspective, but also timing.”

In 2016, legal tech was going through its first big boom. Legal tech, I always describe as like, there's like [inaudible] legal tech, which is just a bunch of people in the wilderness doing random things, like shout out to people who were trying to start legal tech companies in the 90s. It must have been crazy.

Then of course you have legal 1.0, which is e-discovery on the B2B side. Then on the B2C side, something like LegalZoom or Rocket Lawyer or these like lawyer marketplaces. That's like legal 1.0. Legal 2.0 was really the rise of contract management, artificial intelligence, practice management, and Clio and all of this. This was the wave that was starting at this point in time.

It was going deeper into basically automating the workflows of lawyers. This is the first time that lawyers were in a system as it relates to moving a case forward, which is much different than say like e-discovery because e-discovery was like I only used it one time and everything else is still like analog and I'm back to all of this thing.

So legal is going through this wave at this point in time and I'm just able to ride this wave into this new one. My first job in legal tech was with a contract management company and contracts were blowing up during this time. Contracts were super important and you saw the early rise of things like Ironclad and a lot of the contract management CLM type of software companies that were going on. I was just in the right place and the right time being in New York and a time where legal was having its next big bump.

Elise Holtzman: First of all, is there such a thing as legal tech 3.0? Are we there yet? Or we're still in 2.0? Because I feel like you talked about things that in 2.0 have been around for a long, I mean, practice management software has been around for a long time. Now you're at Nexl. If you could tell us a little bit about what Nexl does and whether that's a new wave or something different or it falls into the category of this stuff that's been around for a while.

Ben Chiriboga: Yes, you can see I love evolution. I love things going from one to two, two to three. I'm going to answer your question in a theoretical way. The core motion of evolution is to transcend and include whatever came before it. For example, the human eye, what an incredible miracle. It's insane how we can even see in the way that we did. But our human eye wasn't always like this.

We used to have fish-type eyes and then it just kept on transcending and including, transcending and including, transcending and including. The human body transcends and includes all of our different systems. Within our systems, we have little parts, but the system transcends and includes something else. Whatever is going to come next or whatever is coming next is going to something that transcends and includes the previous level of everything.

What's happening right now with artificial intelligence is a lot of what's happening right now. I'm going to put where Nexl fits in this new wave. Artificial intelligence is transcending, including a lot of previous companies for the very reason that it's taking away the idea of what the clicking and the putting in data and all of that, it's becoming this chat function.

To make something that is so intuitive that as soon as I say you'll understand it, most people, if you're moving away from Google, Google was, “Please tell me the best Thai restaurant in New York,” now you can just ask ChatGPT and pretty soon you'll be able to say, “Book a Thai restaurant for me in New York City that has availability at 6:30 for four people that are above four stars,” and it'll basically be able to do it.

You can see that to be able to do that, first they needed the database of all of the sites on the internet, then they needed the search function that was Google to be able to search very quickly for these, but then the last is it needed a degree of intelligence to be able to do all of that. You can see the new system will transcend and include all of these sorts of things, and I think that's what's happening now.

Nexl sort of, I believe, fits within that because as an all-in-one platform that is bringing together marketing, business development, and lawyers into one platform, we are trying to transcend and include the previous iterations, which might be point solutions in marketing, such as email marketing, point solutions for business development, such as pipeline management, and point solutions for lawyers which might just be practice management or project management or collaboration.

We're trying to bring or just a regular CRM just who do I know and who else knows. We're combining these three things into one that hopefully transcends and includes and creates a better sum of its parts.

Elise Holtzman: I love the way you talk about the evolution of technology having to transcend and include what came before. It actually makes a lot of sense to me because if we think about the things that have been available versus what's becoming available, just in this context, marketing and business development, because that's a lot of the work that we do here at The Lawyer's Edge, we often have clients saying to us things like, "I can't keep track of all this stuff. I don't know where my information is. I can't remember the last time I talked to so-and-so," this is individual lawyers who are trying to keep track of what's going on with them.

Also, the law firm leaders saying, "Well, we have a CRM, but our lawyers won't use it." They're annoyed, understandably so, because they've invested all of this money and this legal technology. Lawyers aren't using it because it's so time-consuming and so clunky. They're supposed to be billing hours. They don't have the time to enter in all these details, enter in the name and the address and where they met someone and what their wife's name is and how old their kids are and all of those sorts of things that you might want to keep track of.

When I see things like lately now you Google something and the AI suggestions come up and it really makes a difference. When it comes to technology, I'm not exactly an innovator. I'm a user and it takes me a little longer to adopt some of these things. But when you see how easy things can become and how natural they can become, I mean, I use it immediately. I've been using ChatGPT. I ask it all sorts of questions. Thank God, I don't trust, I verify.

Ben Chiriboga: That's right.

Elise Holtzman: There was another article in the legal press just yesterday about another lawyer quoting sites that didn't exist in litigation. But it is really amazing to see how this stuff can become naturally usable for us so quickly when it does anticipate what we need and enter in the information without us having to go key things in and that sort of thing.

From a practical perspective, what is the challenge that Nexl is solving for people? And who is it solving it for? Is it for the law firm? Is it for the lawyers themselves? Is it just the marketing and business development professionals? What's the problem and who's benefiting from the solution?

Ben Chiriboga: The answer is, yes, it's solving for everybody. But I'll put a very fine point on it and then I'll tell you a quick story. The very fine point is Nexl is trying to solve the problem of how do you get marketing business development and lawyers to work together to grow the firm specifically. Our bet is that if you give tools on one platform that everybody can go in and use, then you'll start to collaborate much better and you'll be able to grow the firm together.

The data is very, very robust, firms that grow together and work together grow together. If you collaborate, you end up making more money, your clients are happier, full stop. Just look at the work from Heidi Gardner on Smart Collaboration. It's basically the best research that there is out there very, very, very verified. Of course, that just makes sense.

Elise Holtzman: It's very clear. I mean, all you have to do is look at one of her charts and you go, “Oh my god, this is unbelievable.” As you say, it's based on like 15 years at this point of research. Yeah.

Ben Chiriboga: It makes sense quantitatively, but it also makes sense qualitatively. When we started Nexl, we thought a lot about the problems that we wanted to solve, especially at the relationship level specifically. Law is a relationship business. It will always be. I've been giving talks around relationship intelligence. The point of the talk is, yes, technology is going to help you know more about your client by basically just giving you insights as to who you know, how well you know them, who else they know.

When's the next time you should talk to them? Who else should you get in contact with? What's the best route? All of this. This is all going to be easy. It's going to get you to the goal line, just to use an American analogy here, to the 18-yard box, because I love soccer. It's going to get you there. But of course, you have to have a high degree of relationship intelligence, emotional intelligence to actually take it across the goal line to score the goal, to hit the home run.

I'll tell you the story about how this all came and why we focus on relationships specifically. As soon as I tell the story, everybody always nods, but everybody knows the following circumstance and it probably has happened within your law firm. Partner A goes on a client call. Partner A is not prepared before the client call because he hasn't looked up who he's calling. Partner A goes through the client call and unbeknownst to lawyer A, lawyer B has actually had a previous conversation with client A at some point in time.

The client is confused and sees that lawyer A and lawyer B are saying two different things to the same client and don't even know that they're talking. Now, has this happened to me? Possibly, maybe. Does this happen around the world? Absolutely, all the time.

We live in a world where that does not need to happen anymore. It can be as simple as looking at your phone on the way to the actual client meeting. That's where technology is leading us today. Pretty soon it's going to be the standard and clients are going to know that it takes 2.5 seconds to look up what is the relationship history, who else has spoken, and what is going on with that.

If you show up unprepared, that's really not a good look. We live in a world of experience now, especially as legal acumen is starting to be elevated with the help of technology as well. That's why we've focused on relationships. When we set out to Nexl, we wanted to make sure that for lawyers, that was never going to be a circumstance.

You were never going to leave with an egg on your face in a meeting because you just showed up completely unprepared. You've expanded this to say, “Well, yes, the lawyer has the one-to-one relationship with the client, but the marketing team working in conjunction with the lawyer is sending on alerts and nurturing the client. The lawyer with the business development team is working together to move deals forward through the pipeline. Business development is working with marketing to develop key client programs and create experiences for those, and everybody's working together to try to basically grow the firm through a handful of things.”

Elise Holtzman: What I hear when you say all of this is basically this stuff is going to become necessary. People are going to start using this because it's easier for them, it's integrated. It makes a better experience for the client, it enables the law firm to serve the clients more effectively. But at the risk of stating the obvious, we know that when these things become available, then people expect it. Right?

Ben Chiriboga: Of course.

Elise Holtzman: I'm dating myself here as usual, but even when websites first came out, it was nice to have, it was like, “Oh, cool, you have a website.” But very quickly, it became that if you don't have a website you might as well not exist. Then forget about just having a website. What does the website look like? What's on there? All of those sorts of things.

I know that clients are starting to request these sorts of things and demand these sorts of things. What do you think is going to happen to law firms who wait to adopt? Becauase again, going back to the lawyer personality, especially for law firms that don't have a lot of administrative professionals, they may be reluctant to adopt technologies when they don't see that it's proven and it's been used for the last 10 years successfully. What happens to those law firms that are slow to adopt the technologies that we're talking about?

Ben Chiriboga: I recently wrote a post that I'm actually going to put out a bigger newsletter on This Legal Life. That's a plug. It's all about, “Are we in a world of experience? Have we moved into a world of client experience as basically the thing that clients buy?” Now, are we completely there? Absolutely not. The future is never equally distributed.

But if you squint, you can see that every lawyer wants to become a trusted advisor. But what does it mean to become a trusted advisor in a world where anybody can write a memo within 2.5 seconds? Now, of course, not everybody can defend Coca-Cola in a bet-the-farm litigation, but there are not that many bet-the-farm litigation for Coca-Cola.

There's a distribution of work as it relates and most of that work, however, even though that work, most of it is written, most of it is going to be increasingly done, yes, it will have to be delivered by a lawyer in a way, but what are we talking about? We're talking about the experience of a client over the course of a series of matters that end up being the entire client life cycle that a client goes through.

My argument is simply that legal acumen is always important, but it's table stakes. Combining legal acumen with client experience in the short term will be a huge differentiator for law firms. In the long term, it will simply be if you do not have a website, if you do not have a client experience that looks like a cohesive experience across, then it's really not going to work with you.

I will add one lecture layer here, which is Heidi Gardner's data and research is conclusive that basically the firm that collaborates and works together grows together.

In a world where it's increasingly more expensive and difficult to sign new clients and where a lot of the upside profit and margin comes from expanding existing clients by delivering a better service, we're all talking about basically a win-win here between the clients getting a more cohesive experience and law firms ending up being able to grow by expanding market share and wallet share.

When you put those two things together, it will just be a matter of time before that culture gets ingrained. Technology will simply make this as easy as, “Can you please book me? Find me a Thai restaurant within two miles of where I'm at today in downtown Manhattan.”

Elise Holtzman: Companies outside the legal industry have been talking about client experience for years. I remember hearing about client experience or CX like 15-plus years ago and that was just because I had started going to all sorts of conferences and learned everything I could about what was new in marketing and business development and that sort of thing.

I think that lawyers who are stuck on this idea that it is the legal acumen and it is who can better brief and it is who can argue the better case and court, not that those things aren't important but if you're stuck on that idea and you're not paying attention to what research shows us and what other companies are succeeding at doing, I think it's a mistake.

I think it's really good for people to open their eyes to this sort of thing. Many lawyers are. We know that the legal industry is changing rapidly and that the culture is changing rapidly to have people be open-minded about these things and invest in these things. I've seen research demonstrating that law firms' financial investments in technology these days are outstripping most of their other expenses, and there's good reason for that.

Let me ask you this, Ben, as we wrap up our time here together today because as usual, you and I could just go on and on and on. There is a question I ask all of my guests at the end of the show, and it goes like this: there is a phenomenon called the Curse of Knowledge, where experts sometimes forget that what is so obvious and natural to them is not at all obvious to others.

When it comes to culture change, evolution, and innovation in the legal industry, what's a principle or a piece of advice that may seem obvious to you, but is important for people to hear?

Ben Chiriboga: We live in such a technologically sophisticated world that simply will continue to get more technologically sophisticated. This is, remember, technology never gets worse. It only gets better. It might disappear. The Romans had aqueducts and they were very close to a steam engine and then I don't know what happened and everybody forgot and it was like a thousand years and then a thousand years later somebody invented the steam engine.

Technology does disappear however, the technology that is here and hasn't disappeared only gets better as we get into a more technologically sophisticated age. I think that we believe that technology will solve or will come to mediate maybe a lot of the human elements.

What I have seen simply growing a company, the work within Nexl, and how the best law firms in the world are working is that relationships and human one-to-one connections are basically more important than ever before. In a weird way, and my counterintuitive take is always technology is actually going to make us more human, not less, over the long run.

Maybe right now, things are a little crazy, and all of this is on social media and all the rest of it, but in the long run, this will basically be able to bring us closer together. Today, within law firms, what we see is that the law firms are investing in their clients and really becoming trusted advisors through the use of technology, but basically not just relying on the legal acumen to get them there, instead using actual relationship intelligence, emotional intelligence, experience intelligence, thinking about things holistically are really standing out in an incredible way.

I think that's what we need to remember and come back to that I think can get very, very lost, especially whenever we're clouded with a lot of technology. The human-to-human relationship might be all that we have and it's come back to where we started.

Elise Holtzman: It's like the robots aren't taking over. We're all just going to be working better with the technology and be able to develop those relationships even more effectively with the technology that's available to us. I love that view of the world. Ben, thank you so much for being here. It's always a pleasure to talk to you.

I want to thank our listeners for tuning in. If you've enjoyed today's show, please subscribe, rate, and review us at Apple Podcasts, Spotify, or your favorite podcast app. In the meantime, be bold, take action, and make things happen. We'll see you next time.

Thank you for tuning in. If you've enjoyed today's show, please subscribe, rate, and review us at Apple Podcasts, Spotify, or your favorite podcast app. In the meantime, be bold, take action, and make things happen. We'll see you next time.