CCBJ: Why don’t we start with how you both know each other. What brought you together?
Farrah Pepper (FP): Marla and I crossed paths in this wonderful industry about 15 years ago. We first met when I was transitioning in my career from the firm of Gibson Dunn to my first in-house role, which was global discovery counsel at GE. It’s a testament to how wonderful and welcoming the in-house community is that someone I knew—a woman who at the time worked at my now employer, Marsh McLennan—set up a lunch to welcome me to the in-house counsel side. She introduced me to a handful of people that she thought I should get to know and Marla, who at the time was at Goldman Sachs, was one of them.
It was a classic example of kindred spirits meeting each other. At the time, we were both focused on e-discovery, which was a cutting edge and very creative area of the law at that time. Still is, but especially then, and we connected and started to build a relationship based on shared mutual principles of caring about solving problems and being excited and passionate about where the law was going, and our relationship grew from there. It’s a great example of people in the industry taking a moment to help each other grow and learn, and forming a lifelong relationship because of it.
Marla Crawford (MC): I’m almost 15 years senior to Farrah in terms of years, and when I met her, I really saw a little e-discovery sister. I had also been at a big law firm—Jones Day for 22 years—before I went in-house and at the time the way lawyers practiced discovery was fast-evolving, so it was very exciting for me to meet somebody who was just a half a step behind me doing the same thing; someone who had the same values, the same experiences, the same outlook.
I’m really proud of our relationship; the way we’ve grown together, the way Farrah has really lapped me in terms of her knowledge and experience and impact on the industry. But the highlight of my relationship with Farrah was when I went with her family and her two fabulous daughters—who are just mini Farrahs—to Disney World to see the Star Wars exhibits and rides. I am not a ride person, but Farrah and her girls took me on the ride of a lifetime.
FP: Thank you for that lovely memory, and it’s a good example of how, again, our community is full of so many amazing people. I’m so grateful I met Marla at the time in my career when I did, because she gave me someone to learn from and aspire to be, and it means a lot to me that our relationship has grown to the point where we’ve met each other’s family members, spent pivotal moments together and created beautiful memories unrelated to the magic of legal technology and the law.
How has that experience informed your hiring decisions and working within your organizations, which are distinctly different not just in size and scale, but in how many interests you’re serving, both internal and external?
MC: It’s been an interesting journey for me because now I’ve been on three sides of the triangle. I’ve been at a big law firm. I’ve been at a big corporation. and now I am at an e-discovery and contract analytics service provider, where I’ve changed my role just a little bit. Even though I am the general counsel and the only working lawyer in the company, I’m also sitting on the executive team, one of four people running the business day to day. It’s been an interesting journey, and I love the fact that I’m still learning new things every day and trying to do my best. But I think what you might be asking about is this idea of connection, and with my years of making connections in the industry, I’m making every effort to give a hand out and hand up, trying to lead with integrity and, especially, trying to focus on women and other historically marginalized populations who may have not had the chances to do the very best work in the legal industry.
Legal technology is one of those fields that is continually morphing and growing and creating opportunity, and if we identify it, acknowledge it and try to bring people into that fold, I think we’re just doing a good deed.
FP: That was beautifully put. I will add that when I think about my team and how we measure whether we are being successful as a team unit, and also in what we bring to our in-house community, we’ve actually developed principles, which we’ve dubbed them the “Pepper principles,” after yours truly, and we talk about them regularly when asking ourselves, “What are we doing? Why are we doing it? And how do we know if we’re doing it well?” The reason I bring that up is because some of the criteria are exactly what you’d expect—things like time and money, which are usually the most easily measurable—but we also look at other things like quality, which is a lot more subjective and harder to score, and my favorite of all, which is joy. We look at whether we’re making people’s workday more meaningful.
We talk a lot about whether, in every interaction we’ve had as a team, people walked away happier or more excited. Joy doesn’t just shape how my five-person Legal Innovation and Technology (LIT) team relates to our colleagues in our legal department—Marsh McLennan has upwards of 650 employees on the legal and compliance team—we also use joy as the construct to think about how we’re doing with each other. Are we laughing? Are we having fun? Yeah, we work hard, but we also like to find the joyful moments within all of that. For me, that’s a big team element of how we both measure performance and also motivate ourselves to do our best work.
Let’s talk about innovation and the role in your leadership playbook, both managing down, up and sideways?
FP: I would say my DNA, and my team’s DNA, is made out of innovation. When I was in Big Law, I started out as a general litigation associate and ultimately founded a practice group for electronic discovery at that firm before making that leap to the in-house side as the first ever global discovery counsel at GE, at the time a massive global organization. That led to my current role as Marsh McLennan’s chief legal innovation counsel. At this point, I have literally got innovation in my title. Innovation, to me, is a mindset inherent to leadership. Great leaders look back— they’re guardians and stewards—but they also look forward. They have to be creative problem solvers and growth-drivers, especially within an in-house organization.
Innovation, to me, unlocks the future while building on the lessons of the past. That change mindset—that ability to evolve and relentless commitment to excellence and iterative improvement—are all hallmarks of great leaders, and that’s where I strive to personally be and what my team and I talk about a lot. In our organization, we’re the engine of what’s next. We’re constantly looking at the holy trinity of people, process and tech to figure out where we’re going to take our legal department next, so everyone can do the best work they can do, infused with that feeling of joy.
MC: For me, as the general counsel of Cimplifi, innovation is basically what we talk about all day, every day because we’re all about innovating and solving our clients’ problems. So innovation is also in my and our company’s DNA. What we love the most is when our clients come to us and say, “I wish a particular tool could do this” or “I wish you had a tech solution that solved this problem,” and then we—and I mean “we” in the broad sense of the company—we go out and build it. Most of the Cimplifi CI innovations are actually responses to things that our clients wished for, and that is very exciting for us. We have a very nice partnership, in particular with Relativity, where we have built innovation on top of their tools, and it’s super exciting when our clients feel heard and seen and their work can be done faster and more efficiently.
Personally, it surprises me that I’m in the innovation field, because my background as a public policy major and as a lawyer was not really all about innovation. Remember, I went to school before computers were commonplace, so while it was something I took to and adopted, it’s really not at the core of who I’ve been, and I push myself every day. I think about the social media posts of people I went to school with, where they’re still posting about how great the ‘70s and ‘80s were, and that, to me, is a reminder that yes, that’s still my jam, but I also need to think future-oriented, to push myself to understand what’s new in the marketplace and what we as a society and, more specifically, our company, are capable of in terms of e-discovery and contract analytics.
FP: I love that answer, and what sprang to mind as Marla was talking is that you might dub us both “legal innovation fairy godmothers” in that we’re in the wish-granting business. Both wishes that people can articulate and wishes that people may not yet know they have. There’s a common saying, “You’ve got to skate to where the puck is going to be.” I think Marla in her role at Cimplifi and me in my role at Marsh McLennan are in the business of seeing ahead, designing for it and helping people get to that brighter future.
Do perceptions of innovation differ depending on whether you’re working in a mature organization vs. a startup?
MC: At Cimplifi have a whole host of clients, large and small, with whom we interact who are trying to push the envelope. Most of the people that we deal with are very tech-forward, very innovative, wanting to employ technology to solve problems, but they’re also interacting with their leadership, their C-suite, and we see two things. We see some corporations where the leadership is looking for some quick wins. They want to adopt AI, to say they’re genAI-forward, that they use technology in their day-to-day operations to report to their boards, to the community, to their customers, to their shareholders.
They’re looking for some quick wins and, luckily, legal can do that. Legal can do that in contracts by using AI modeling to understand what’s in a volume of documents. Legal can do that in e-discovery to review documents using AI. Legal can do that in terms of summarizing and categorizing documents with genAI. Legal is in the best position in the company to really adopt the innovation and show the quick wins leadership is looking for. The other thing we’re seeing is some trepidation among leadership. They’re worried about security and accuracy in terms of using AI in some innovations. Again, legal is perfectly-positioned to address that. Legal is traditionally slow-moving, conscious of security issues, accuracy and efficiency. Legal has obligations to the court, and under the rules of evidence and civil procedure. To me, the pivot point for all of this, whether you are innovation-interested or innovation-afraid, is to go to your legal department, to find your innovators there, and to work with them and move forward at the pace that the enterprise is prepared for.
FP: I will add that I think this is an incredibly exciting time to be in the legal profession. On the in-house side, we sometimes battle what the perception that legal will slow things down, that legal is not where you would go for cutting-edge creativity or innovation. We have successfully changed that mindset within our organization. In fact, today, the hubbub around AI which has increased general awareness of technology and tools and processes across the entire company, has come as a surprise to some, but not those within legal who’ve been on the cutting edge. We’ve got tools and processes that the rest of the company can and does adopt, such that we’ve become the innovators and business accelerators. Will legal sometimes say no? Sure, but only when we have to. We come from a place of yes, a place of how do we help the business achieve its goals. Of course, in a compliant and appropriate way, but what we’ve found is that all of the great work that’s been going on for a long time within spaces like discovery are now building blocks that everyone can leap off of, and not just the legal department, but the entire company can benefit from.
Those professionals who started out in that space within legal and who’ve been doing this for a very long time, including AI, have spawned the Legal Data Intelligence (LDI) movement, which is a response to legal’s need for new vocabulary, a new framework, and new roles and titles to reflect that what’s already been going on. It’s about harnessing the power of data, the power of tech to, advance the legal profession and outcomes. I think this is the greatest time to be in the profession, because once again, it’s evolving and changing, and those who’ve been at this for a while are particularly suited to help us get to that next level.
Let’s talk a bit about what’s personally motivated you throughout you careers. Marla, do you want to jump in?
MC: I went to law school because I had watched my father, an individual plaintiff’s lawyer, help real people with real problems. I thought it would be interesting, intellectually challenging, and also a way to impact people’s lives. In fact, in my office, I have a framed bumper sticker that a client gave my dad which says, “My lawyer can beat your lawyer,” and it’s honestly one of my prized possessions. I decided to go into big law and to do what I could in terms of working on big cases and getting trained and educated.. Because I had a lot of experience working on cases with huge discovery efforts, I was put on the Enron case for a client, Lehman Brothers, to lead the discovery, and that literally changed the path of my entire career.
I was just in the right place at the right time doing the right thing. Ever since then, it’s been an exciting journey, learning the technology and how the law changes and adapts to technological changes, I believe technology has changed the practice of law more quickly than any other societal event in our history. I’ve never lost that interest in and fascination with technology and innovation and how that translates into, “How do we solve problems? How do we move the needle—for Cimplifi, our clients and our customers, and for the pro bono work we do—to help real people solve real problems?”
FP: I’ve always had an attraction to, affinity for and skills in storytelling and problem-solving. I initially started on a path where I wanted to be a journalist and a writer, and over time, that evolved into wanting to focus on First Amendment law as a lawyer to protect storytelling, if you will, and to solve problems in society. So I graduated from law school, started at a fantastic firm and, not surprisingly as a junior attorney, found myself doing a ton of, you guessed it, discovery because that is bread and butter of early years of a career in Big Law, going deep into that as a litigator. What immediately attracted me was what I saw as a giant chaotic problem that needed to be solved. The industry had not yet come up with the vernacular, the frameworks, the tools, the repeatable processes—the vision, if you will—to make that a solved problem.
It was big. It was bloated. It was messy. It was expensive. In short, there were a lot of problems that needed to be solved, and that’s what attracted me to the path that I found myself on. I would say the common thread through everything that I’ve done is I’m a builder and I’m a doer. That’s inherent in my nature. But I’m also a helper and a solver. So building something new in an uncharted area that helps people is my sweet spot. That is where I thrive, where I find meaning and value, and where I think I can help to advance the profession.
Can you share some of the tricks of the trade that you’ve developed over the years to maintain work-life balance?
FP: I’ve thought about this a lot because there’s a lot of discussion how to achieve that elusive thing called work-life balance, and the working assumption I’ve come to is that there is no such thing. Balance, to me, conjures up an image of spinning a lot of plates where you’re trying to keep them all equally aloft at the same speed which, unless you’re a circus performer who trained for that, is impossible to do. Some plates are going to come clattering down. I don’t like the construct of balance because right out of the gate it presumes something unfair and likely unattainable. Instead, I like to think of it as juggling. There’s really only going to be one, maybe two, balls in the air at a time, but when they’re there, they have my full focus, and that’s been my personal approach.
I can’t do everything at the same time, but I can give my full energy and attention to what I am doing at that time, and try to structure things so that there’s not just one ball getting attention. To juggle, you need a lot of different things going on. That’s my best attempt to reframe the imagery around this, because I’ve struggled for a time with the notion of balance. If that’s what we’re trying to do, I’m not sure anyone truly gets there.
MC: Life is hard! No matter what you’re dealing with, whether it’s work and family life, or any other two things, it’s really hard. I don’t know if I have any special learning about this. It’s easy when you have no choice, but the more choices in life you have, the harder it is to make them, so I had to work and I had kids and I just had to keep going. Now my daughter actually works at the law firm I worked at as a lawyer. She’s a fifth-year associate, and she’s expecting my first grandchild. I’m watching her make the same choices and decisions and deal with having to be torn between two places.
I would say be kind to yourself. Nobody is perfect, there are no right and wrong answers. It’s what works for you, what you choose. If you make a mistake, you can probably change your mind and have a redo, or do it differently the next time. But people should just be kind to themselves, because the world is a difficult place to navigate. We are continually learning and evolving, and we should give ourselves the freedom to change.
Is there anything else that you think that we should touch on that looks towards the continued development of the industry, but also more on an interpersonal level?
FP: I’ll take that one first. I am so grateful and honored to have had a chance to be part of some of the leading industry organizations in our field that are truly shaping the future of law, but perhaps more importantly, creating connections between these smart, kind, impressive individuals who are off within their own organizations doing amazing work and then get to come together through this giant community by working together through these industry organizations. Some of those experiences for me have included being part of groups like EDI (the Electronic Discovery Institute); CLOC (the Corporate Legal Operations Consortium), which I’m currently honored to sit on the board and be vice president; and the College of Law Practice Management, which celebrates innovation in the practice of law.
There are a lot more great organizations out there and also events. But it really becomes a “community of individuals” who get to share ideas; to be inspired and inspire others. Frankly, it’s one of my favorite parts of this corner of the legal industry. I’ve lost track of the number of great ideas that I’ve heard by being able to connect with other people through these organizations, all of which are volunteer-based and to which people take time out of their very busy days to contribute. For anyone who’s thinking about how to make connections or how to advance their own thinking, any of the organizations I mentioned and more are a great place to start.
MC: Absolutely. I’m in many of the same organizations and it is all about community. Joining one of these organizations, attending conferences, being friendly and meeting people is the way to ingratiate yourself in the industry, find out about opportunities, learn about new technologies, and make lifelong friends. Farrah and I are at a lot of the same events, in the same groups, with the same organizations. We have a lot of friends in common, and when someone needs something, the legal technology community really closes ranks and helps each other out. Getting involved—putting yourself out there—is very valuable and I recommend it to everyone.
FP: I should add that another one on that list is the aforementioned Legal Data Intelligence which, while new, is currently in the process of putting together working groups to create resources for the community. And just like Marla was saying, it’s all volunteers who are willing to help people by sharing ideas, insights and tools of the trade, talk job roles, contribute to white papers, and more, to help advance their teams and their visions within their respective organizations. It’s a great place to get involved.
Published April 23, 2025.
