JANUARY/FEBRUARY EDITION
VOLUME 33, NUMBER 1

JANUARY/FEBRUARY EDITION
VOLUME 33, NUMBER 1
SARAH HAMMER ON LEADERSHIP, AI AND SHAPING THE FUTURE OF FINANCIAL SYSTEMS
Litigation Funding Attracts Wave of First-Time Users, Gaining Mainstream Momentum
Navigating Today’s Complex Regulatory Chessboard Requires a Trusted Advisor
Forging Connections & Driving Legal Innovation
Deploying Dedicated, Dynamic Legal Intake Software Lets Lawyers Be Lawyers
Harness the power of Artificial Intelligence with ClauseBuilder AI. Trained on almost 100 years of expertise, this free-to-use breakthrough tool utilizes generative AI language models based on a history of clauses to draft effective arbitration and mediation agreements tailored to your industry needs. With ClauseBuilder AI, the future of dispute resolution is here.
The participants in the CCBJ Network demonstrate, through their many contributions, their unwavering commitment to the advancement and success of corporate law departments. The engagement and support of these “partners of corporate counsel” assure we continue to develop and distribute the news and information this unique and sophisticated audience relies on to meet the evolving legal and business needs of their organizations.
Agiloft
American
McGuireWoods
Mitratech
Onit
Thomson
Advisors
CobbleStone Software
Diligent
Epiq
LexisNexis
LexisNexis CounselLink
NetDocuments
Purpose Legal
Contributors
Association of Corporate Counsel
Casepoint
CLOC
Consilio
DXC Technologies
Epona
Linksquares
mot-r
OpenText
Reveal
SCCE
Litigation funding continues to make significant strides toward becoming a mainstream source of legal financing, according to Bloomberg Law’s 2025 Litigation Finance Outlook. The data underscores this rapid growth, revealing that nearly twothirds (66 percent) of litigation funding clients in 2024 were utilizing these services for the first time. This influx of new clients highlights the widening acceptance of litigation finance as an alternative to traditional contingency fee structures, particularly among major law firms and corporate litigants.
Yet, even as litigation finance attracts fresh interest, challenges remain. The industry faces a fragmented regulatory environment, with recent state-level legislation in Indiana, Louisiana and West Virginia imposing restrictions on funders’ ability to influence litigation decisions. Meanwhile, federal attempts to standardize disclosure and transparency have uncertain political futures.
To further bolster confidence, the industry is turning to complementary financial tools such as insurance products, which mitigate risks and offer more flexible funding arrangements. Additionally, the emerging secondary market is introducing liquidity and competitive pricing, promising advantages for funders and litigants alike.
Ultimately, the continued mainstream ascent of litigation funding depends upon how effectively the industry addresses regulatory hurdles and client concerns about cost, procedural complexity and maintaining litigation control.
Mark Tibberts Welcomed to Moore & Van Allen’s Financial Services Practice
Zachary C. Schauf, Former DOJ Deputy Assistant Attorney General, Returns to Jenner & Block
Ashley Lynam and Jacob Sand Added to Morgan Lewis’ Two-Partner Disputes Litigation Team in Philadelphia
Welltower Announces Executive and Senior Leadership Team Promotions
Carlos Ortiz Retires After 35 Years at Goya, Jesús Vázquez Appointed New General Counsel
Aaron Wolfson, WhiteCollar Litigator, Joins Fox Rothschild in New York
Tony Torain, New Labor & Employment Partner, Welcomed at McDermott
Partners Hoyt Sze and Margia Corner Continue Sheppard Mullin’s Healthcare Team Expansion
Cahill Announces Election of Four New Partners and Two New Counsel
Errin Martin, Former Federal Prosecutor, added to Thompson Coburn’s Business Litigation, White Collar Practices
Morrison Foerster Counsels Pharma Company on Acquisition of Treatment Drug Galzin®
Vedder Price Represents Tortoise Funds in Strategic Initiative
Richmond-Based State Lobbying Practice Spins Out from Reed Smith
Buchanan to Launch Chicago Office with 17 Intellectual Property Litigators
DEI initiatives have faced increasing scrutiny through legal challenges, executive orders, and shareholder pressures. While some companies have scaled back their efforts following the Supreme Court’s ruling against affirmative action, major corporations such as Target, Nike and Costco continue to support DEI, recognizing its business value.
DEI aims to create diverse workplaces, ensure equitable hiring and promotion and foster inclusive cultures. Organizations that embed DEI into their broader business strategies, rather than limiting it to human resources, tend to be more resilient and better positioned to attract talent in an evolving demographic landscape.
Legal challenges, citing civil rights laws, are prompting businesses to reassess their DEI programs for compliance. Some companies are rebranding DEI initiatives to maintain inclusion efforts while mitigating controversy. However, multinational corporations must consider global diversity regulations, which remain robust in many regions.
Rather than a widespread rollback, the current environment presents an opportunity for companies to refine their DEI strategies. By aligning these initiatives with long-term business goals and ensuring legal compliance, organizations can maintain inclusive workplaces while adapting to shifting regulatory and political landscapes.
Source: Legal Dive
KPMG’s legal head, Stuart Bedford, predicts U.S. corporations will increasingly turn to the Big Four for legal work due to their advanced technology for handling large-scale data and contracts. He noted their ability to streamline post-merger integrations and supply chain shifts.
KPMG aims to be the first Big Four firm to launch a U.S. legal venture, pending Arizona Supreme Court approval. Arizona allows non-attorneys to operate law firms to expand legal service access.
While KPMG seeks to complement law firms, some displacement may occur. Bedford cited UBS’s Credit Suisse acquisition, where elite firms closed the deal, but Big Four firms are better suited for post-merger integration.
A former Linklaters partner, Bedford emphasized cost savings as a key advantage. Unlike law firms constrained by partnership models, the Big Four reinvest profits into superior technology. While top firms will still handle high-value deals, he sees collaboration, with firms like KPMG managing complex reorganizations.
Source: Bloomberg Law
Thanks to the law firms, technology companies, alternative legal service providers, management consultants and other supporters of corporate law departments who share their insights and expertise through the CCBJ network. Your participation is appreciated.
Crawford brings more than 35 years’ expertise to her role as General Counsel of Cimplifi. She is a respected attorney, strategic advisor, and thought leader who speaks regularly on legal operations and technology, electronic discovery, and contract analytics. Marla spent 22 years practicing law at the prestigious international firm, Jones Day. She also served as associate general counsel for Goldman Sachs for 11 years.
From restoring classic cars to serving as an accounting executive and entrepreneur in e-discovery, Sue Pellegrino has challenged the status quo around what a woman leader can be her whole life. Sue has spent her career managing organizations’ finances, ranging from publicly traded companies to regional enterprises and small businesses. Now, she runs Everest Discovery, taking the business to new heights.
Hammer is the Executive Director at the Wharton School. She leads strategic initiatives across Wharton Finance and is Founder and CEO of Wharton Cypher Accelerator. Hammer is also Adjunct Professor at the University of Pennsylvania Law School and Affiliated Scholar at the Penn Program on Regulation. Previously, Hammer was Managing Director of the Center for Innovation in Finance and Senior Director of the Alternative Investments Program at Wharton.
Pepper is the Chief Legal Innovation Counsel (CLIC) at Marsh McLennan, where she makes things… click. Farrah created and leads the company’s Legal Innovation & Technology (LIT) team, including the LIT Lab (legal innovation lab) and the legal data discovery program. Farrah is a sought-after speaker and educator in the legal community, as well as an active participant in leading industry advisory boards and organizations.
is nationally recognized in crisis management, white collar investigations and national security law. His highlevel government and business experience enables leaders to proactively manage complex risks and crises.
Evan Wong co-founded Checkbox in 2016 with James Han and Paul Wenck. At the age of seventeen, Evan founded Hero Education, an award winning education company that impacted thousands of to-be-adults. He then founded Sequoia-backed enterprise software company Checkbox (a $1B company in the making) and have helped many large enterprises empower their people to do more meaningful work through AI and automation.
Brydne Slattery Joins Captona as General Counsel to Support its Accelerated Growth in Full Acquisition and Preferred Equity Transactions
Ryan Majerus, U.S. Department of Commerce Trade Official, Joins King & Spalding’s International Trade Team
Dr. Larry Bucshon, Former Indiana Congressman, Joins Holland & Knight in Washington, D.C.
Brandi Howard Returns to McGuireWoods
Timothy Reilly Joins Snell & Wilmer’s Denver Office
David Grimes and Patrick Rowe Added to Alston & Bird’s M&A and Private Equity Practice in New York
Epiq Announces Epiq AI Discovery Assistant™ and Epiq AI Labs
Epona and JustiSolutions join forces with the support of Main Capital Partners
Kevin Lanouette Named Senior Vice President and General Counsel of iRobot
Caroline Geiger and James (“Jamie”) Talbot Have Joined Simpson Thacher’s Intellectual Property/Privacy Team
David Harris Enhances Ropes & Gray’s M&A Team in New York
Jesse Nevarez, Experienced Emerging Companies Partner, Added to Morrison Foerster’s Team in New York
Jennifer Santa Maria, Former Department of Justice Attorney, Reunites with Ogletree Deakins in San Diego
We are thrilled to present our 10th Annual Directory of Leading Legal Technology and Project Management Solutions, formerly the In-House Guide to Tech, from CCBJ. Over the years, this guide has served as a solution for our many readers who look to bring new and innovative solutions into their corporate environment. We are incredibly fortunate to have access to many subject matter experts who represent any number of industries and solutions within the legal ecosystem.
JONATHAN LENZNER FENWICK & WEST LLP
Jonathan Lenzner, partner in Fenwick’s White Collar Defense & Investigations practice, discusses the ways that his background as a former U.S. attorney and chief of staff for the FBI will inform his new role at Fenwick, from helping clients avoid regulatory pitfalls to advising them about opportunities and partnerships with various government agencies. Plus, drones over New Jersey and his take on the Trump administration 2.0.
CCBJ: You recently joined Fenwick as a partner in the firm’s White Collar Defense & Investigations practice. You’ve had an interesting and high-profile career. Can you tell us a bit about your background, as well as what drew you to Fenwick in particular?
Jonathan Lenzner: I was born and raised in Washington, D.C., and after college I worked on Capitol Hill, where I was a press secretary and then a media strategist. From there, I went to law school. It’s funny, I went to law school because I thought it would help with the work I was doing on campaigns and on Capitol Hill. I thought that if I got a law degree, then in the future if a lawyer on a campaign told me that I couldn’t put something in a TV ad or a radio ad, I would be able to push back. But when I went to law school and I tried my first case, I fell in love with that.
So, from there I went to the Manhattan District Attorney’s office, where I had a chance to try a few cases, and loved that and loved public service. Then from there, I moved back down to Washington, D.C., because there was a job there that my wife wanted. I became an assistant U.S. attorney with the Maryland U.S. Attorney’s office, which I did for almost three years.
From there, I made another out-of-the-blue pivot and took over a risk advisory, corporate investigations firm that my father had founded back in the early 1980s. That was one of the more interesting and significant educational experiences that I’ve had in my career, because I’d never run a business before. I think as you get older, once you’re in a seat of responsibility, where it all falls on your shoulders, so to speak, and you feel that pressure, you can do great things, especially when you’re motivated by keeping the business going.
There were some challenging years, but by the end, it was an amazing experience. I brought in a great team, and we had some great clients. I learned a lot about how to run a business and how to grow and improve a firm and an organization. And ultimately what I found that I valued most were my relationships with the clients. Whether they called me a lawyer or a counselor or their crisis manager or investigator, at the end of the day, I just wanted them to think of me as their trusted advisor – a trusted advisor who could solve problems and anticipate and mitigate risks.
Then, out of the blue, once again – these things seem come up out of nowhere – I was asked to go back to the Maryland U.S. Attorney’s office. But this time it was as the first assistant U.S. attorney, which is essentially the deputy U.S. attorney. Even though I was back in on the government side now, I tried to retain some of that entrepreneurial spirit that I had acquired running the corporate investigations firm. In particular, within the areas of cyber and national security, I tried to bring some new solutions to the Department of Justice.
Then in 2021, Maryland’s U.S. attorney stepped down, and I took over that role, which was a great honor and a great opportunity. One of the things I did there was start the office’s first civil rights unit. Then I spent a brief period as a senior advisor to the Drug Enforcement Administration (DEA) administrator, which was fascinating because we were focused on opioids at that point. I helped the DEA think about new approaches to regulating and enforcing laws around opioids and opioid abuse.
After that, I had an opportunity to interview with the Federal Bureau of Investigations (FBI), as former director Chris Wray’s chief of staff. I jumped at that. The FBI is an amazing organization, with 38,000 full-time people. It’s a global law enforcement and intelligence agency. And since 9/11, it’s been our nation’s lead domestic intelligence agency, focusing on everything from cyber intrusions to counterintelligence, counterterrorism, public corruption, financial fraud, health care fraud and so on.
The chief of staff at the FBI is part of the senior leadership team, along with the director and deputy director. The chief of staff essentially helps the director run the agency. One of the things Director Wray made a priority was strengthening the FBI’s relationships with critical private sectors, so that we could better protect American businesses, American innovation and American technology at scale. I worked closely with Director Wray to develop those relationships.
In this context of working with companies across the country who were developing and working with emerging technologies, I realized that in my next role I wanted to make sure that I continued in that vein – working with companies that are leading the way in terms of the future of our country, whether it’s national security, energy, economic security, health care, etc.
When exploring my next chapter after the FBI, I talked to a number of different potential employers, including a number of law firms, one of which was Fenwick. What really struck me about the lawyers at Fenwick is that they are all highly competent and highly skilled in their areas. Many of them had prior careers in very technical areas – there are engineers and developers and PhDs and scientists who are now at Fenwick as lawyers. They take the work they do for their clients very seriously, and they immerse themselves in their clients’ goals, challenges and operations. And that’s how I operate too. So I really felt a natural connection to the Fenwick lawyers and the Fenwick clients.
I really relish the opportunity to work with an entrepreneurial law firm like Fenwick that works closely with entrepreneurs who are developing new technologies,
whether it’s in artificial intelligence and machine learning or different areas of cyber technology – drones, counter drones, counter unmanned systems, for instance. Looking over the horizon, based on my experience at the FBI, those are areas that are going to be very impactful for our country. So the opportunity to help these companies and their founders grow, to help them succeed – I thought that was a very attractive, unique opportunity, and very different from other opportunities I had explored.
We don’t hear often enough about attorneys with this kind of elevated technical competency, especially when it comes to working with startups. When you were talking about political campaigns earlier and what you can and can’t put into ads, and then about opioids, it made me think about the idea of unintended consequences – the way people can sometimes create a fantastic product that suddenly makes a left turn, especially in the eyes of the government, instead of the path that was originally intended. And they’re going to need a trusted advisor, as you said, to help them either avoid that turn or navigate their way through it.
That’s right. That’s exactly right. And that’s one of the things that I thought would be interesting from the perspective of developing a practice. I’ve run a business. I’ve been the CEO of a company. I’m familiar with the challenges and pressures of running a business. So, my goal is always to be a trusted advisor who is a problem solver for clients – someone who helps clients see around corners, someone who helps them anticipate and mitigate situations. In the last few years, having been on the government side, I know that the companies that are working on these developing technologies are increasingly relevant to what’s happening in D.C. Even if the company itself doesn’t care as much about what’s happening in D.C., there are plenty of agencies that care about what the company is doing, for all sorts of reasons.
Fenwick has a long-established history of relationships and credibility in the startup community in Silicon Valley, so I knew it would be a great place to grow a practice. We want to be a solution for those companies – a solution in Washington. Fenwick knows those companies, knows their culture, knows their operations, knows their
My goal is always to be a trusted advisor who is a problem solver for clients – someone who helps clients see around corners.
challenges. And Fenwick is also invested in lawyers like me in Washington, people who come out of the government and have been in the room when critical decisions have been made at the highest levels of government. So, at Fenwick, you get the long history and relationships and technical expertise of lawyers who work in Silicon Valley with startups and public companies, but you also get that expertise in Washington.
That’s important, not just when there’s an issue that comes up with a government investigation or congressional scrutiny – it also provides clients with an opportunity to go on the offensive, especially as we’re heading into a new administration and a new congressional term. There are these developing technologies, in different sectors, and there are also a lot of questions about who will be leading various agencies, what their priorities will be from a regulatory standpoint. That can create uncertainty, and as a prior business owner I know that what they want is certainty. So, being able to help companies navigate that landscape of uncertainty is one of the really attractive opportunities at Fenwick.
You were talking earlier about unmanned vehicles –drones, for instance – and how they are regulated. They were primarily considered recreational for many years, basically toys for hobbyists, but recently the technology has greatly improved, to a point where lately it seems like people aren’t even sure what these things are currently capable of. I’m thinking of the all the drama here in the Northeast during the last couple of months with the drones over New Jersey, where people are really wondering, “What are they, where did they come from, and what are they capable of?” And obviously there are also huge concerns there in terms of national security
and some of the other things we’ve been discussing. So, when you look at these kinds of tech companies, how are you advising them about what’s coming around the bend in terms of government regulations, trade secrets, staffing, etc.? What industry norms are they following? It seems like all these areas are evolving very rapidly.
It’s interesting. Whatever companies I’ve worked with –whether high-tech or otherwise – I’ve always tried hard to spend time getting to know them. I want to understand their operations, their goals, their challenges. Then I try to bring my knowledge and expertise from working in Washington to help the company see potential issues they may not be focused on yet. They’re primarily focused on growing their business, as they should be. But I can help them look for additional opportunities and even go on the offensive. And that can mean a lot of things. People mainly think about government enforcement, regulatory enforcement, and that’s obviously an area that I know well, but there are also opportunities the government presents that can advance your business.
The most basic opportunity is a government contract –working for the government as a client. But the government is also constantly looking for opportunities to help certain businesses and sectors, so I look for areas where we can leverage those relationships. We might have clients, for instance, whose business can help advance the FBI’s intelligence and law enforcement mission. That’s just one example. Across the various executive agencies, there are all kinds of opportunities for companies to benefit, whether it’s through relationships, or through funding, or through various kinds of projects. It’s helpful to provide clients with those perspectives that they may not be aware of – not only the potential problems but also the potential opportunities.
How the client is defined from a business perspective is something that I try to understand, so that I can help them advance their business goals. If you’re dealing with a regulator or a congressional committee or a law enforcement agency, the goal is to resolve that issue in a way that does not disrupt the business. The best advocates are the ones who really understand their client’s business
challenges and goals, so that they can keep those goals in mind as they work to resolve whatever the issue is in Washington and get the best outcome for the client. That’s what I try to do.
Let’s broaden the scope a bit further, beyond the governmental concerns, whether it’s avoiding regulatory enforcements or, on the other side, taking advantage of opportunities for partnerships like you mentioned. What about the public relations side? Is it part of your role to convey concerns about optics or public perception – as in the case of the drones, for instance?
Well, that’s an aspect of it, but it’s really just one piece on the chessboard. There has been a lot of public attention, as you noted, paid to these alleged drone sightings. The regulatory framework for drones – as well as for counterdrone technology – is continuously evolving. And even though people may think of the government as monolithic, it has many, many parts. There’s Congress, there are the executive agencies, there are state and local governments, there’s the Federal Aviation Administration, and so on. And yes, as you said, there’s also public perception. All those things are intertwined.
What I do is work with clients to help them see how all those different pieces on the chessboard fit together – and in 2025, there are many different adjacent pieces that may seem unrelated to the client but which can greatly impact one another. That’s definitely something that we are expected to do for our clients. Beyond knowing what to file with a court or what to send back to an agency, we also need to think about the other implications, whether it’s the public relations aspect or whether some potential civil litigant might grab ahold of this or that later. Will Congress latch onto it later? There are a lot of different potential factors.
So, yes, I have to think about all the potential pieces on the chessboard, including the ones the client is not even aware of, to help them anticipate and take decisive action. I want to offer the client as much information as I can to help them think about these issues in different ways.
Great. Let’s wrap up with your perspective on the new Trump administration, particularly in terms of them opening some regulatory doors. There’s certainly a lot of activity there – and a lot of enthusiasm and optimism on one hand, but also skepticism and pushback, depending on how people feel about the importance or necessity of certain regulations. What’s your take on that?
From a business perspective, there have been signals from the new administration about their openness to working with certain industries – artificial intelligence being a big one, for instance. But that doesn’t mean the rules will be suspended. Fraud is still fraud, and there are still regulations that companies need to follow. But there are opportunities to shape the way forward in terms of the regulatory landscape. There are also opportunities to work with the various agencies in this new administration to find opportunities that are good, that make sense for the business but also help the country.
That is something that people don’t always understand from the outside. The government, by and large, is fairly probusiness. When I was at the FBI, we were very motivated to work with companies to help us achieve our mission. And I know other agencies are looking to do that as well. So I think there will be a lot of opportunities in the next few years for businesses to continue to develop their products, systems and platforms –and to do so in a way where Washington is working with them.
MARLA CRAWFORD CIMPLIFI FARRAH PEPPER MARSH MCLENNAN
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
Legal has obligations to the court, and under the rules of evidence and civil procedure. - Marla Crawford
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
Marla Crawford brings more than 35 years’ expertise to her role as General Counsel of Cimplifi. She is a respected attorney, strategic advisor, and thought leader who speaks regularly on legal operations and technology, electronic discovery, and contract analytics. Marla spent 22 years practicing law at the prestigious international firm, Jones Day. She also served as associate general counsel for Goldman Sachs for 11 years.
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 volunteerbased 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.
Pepper is the Chief Legal Innovation Counsel (CLIC) at Marsh McLennan, where she makes things…click. Farrah created and leads the company’s Legal Innovation & Technology (LIT) team, including the LIT Lab (legal innovation lab) and the legal data discovery program. Farrah is a sought-after speaker and educator in the legal community, as well as an active participant in leading industry advisory boards and organizations.
SARAH HAMMER WHARTON SCHOOL
Sarah Hammer on leadership, AI and shaping the future of financial systems
CCBJ: Can you share your career journey and what led you to Wharton?
Sarah Hammer: I’ve had the privilege of leading organizations through major financial sector events, shaping the regulatory frameworks that govern our financial systems, and mentoring the next generation of leaders at the intersection of finance, technology and innovation. These experiences have deeply shaped my perspective on what effective leadership truly means.
Early in my career, I worked in research at Tudor Investment Corporation, a global macro hedge fund, where I was exposed to macroeconomic analysis and investment strategy. I also worked at BlackRock’s Portfolio Analytics Group, where I focused on building quantitative models. These early roles helped me understand how markets, economics, and quantitative analysis intersect in driving financial decision-making.
I then joined JP Morgan, initially in New York and later in Tokyo, structuring and marketing fixed-income derivatives for large hedge funds. I eventually transitioned to managing the credit derivatives trading book in Tokyo, which was particularly challenging during the aftermath of September 11, 2001. Tokyo was the first market to open after the attacks, and that experience taught me invaluable lessons about crisis management and leadership under pressure.
I then moved to PIMCO, where I worked in portfolio management, developing and implementing fixed-income and FX strategies for institutional clients. After PIMCO, I joined Vanguard, focusing on investment strategy and regulatory matters, particularly around nonbank systemic risk designation.
In 2017, I had the opportunity to serve as Deputy Assistant Secretary for Financial Institutions at the U.S. Treasury.
I led the development of a comprehensive report on the U.S. financial regulatory framework, collaborating with business leaders, regulators and key stakeholders in the financial sector.
I joined Wharton in late 2017 as Senior Director of the Alternative Investment Program, focusing on private equity and venture capital. When we received funding to launch the Center for Innovation and Finance, specializing in digital assets and financial technology, I took on the additional role of Managing Director.
Last year, I took a leave of absence to serve as Secretary of the Pennsylvania Department of Banking and Securities, where I led the Department through the 2023 Banking Crisis, overseeing 290,000 financial entities with $3.5 trillion in assets. It was a deeply intense experience.
Upon returning to Wharton, I stepped into my current role as Executive Director. Now, I lead several strategic initiatives, including the Wharton Cypher Accelerator, which launches emerging technology companies, particularly those in AI and blockchain, and the Wharton Future of Finance Initiative, which brings together leaders from finance, technology, policy, and government to address critical issues in the financial sector.
I’m also actively involved in shaping policy across the global financial ecosystem. I teach financial regulation and alternative investments at the University of Pennsylvania Law School and participate in several international organizations. For instance, I co-chair the International Expert Consortium on Artificial Intelligence (RECSAI), where I lead global discussions on AI regulation and implementation. I’m also active with the Bretton Woods Committee, where I co-chair the AI in Finance Working Group, focusing on policy and best practices at the intersection of AI and financial services.
It’s incredibly rewarding to be involved in these global conversations and to collaborate with remarkable people from around the world.
What important traits do you believe define a leader, and how has your diverse experience contributed to your leadership capabilities?
Throughout my career, I’ve learned that exceptional leadership requires a balance of steadfast principles and dynamic adaptability. Leadership excellence is something that’s intentionally developed. It involves being open to coaching, embracing new experiences, and continually learning.
Leadership is more than just management. While good management ensures operational efficiency, true leadership involves setting a bold vision and inspiring others to achieve what might seem impossible. This requires courage, especially in times of transformative change. Take artificial intelligence, for example—it’s fundamentally reshaping society, and embracing this level of change requires intellectual curiosity, wisdom, and sound judgment to guide us forward.
Leaders must also be able to consider problems from multiple viewpoints and build relationships with diverse stakeholders. Early in my career, I often used the phrase “connecting the dots” to describe how different parts of an ecosystem interact. I think of it as a three-dimensional chessboard: you need to understand how relationships work, what motivates people and organizations and which patterns are emerging. In my world, which involves finance, economics, geopolitics, regulation and innovation, understanding these interconnected systems is essential for making informed choices.
In both business and government, I’ve had the chance to dive deep into emerging developments—whether it’s technological advances, geopolitical shifts or societal changes. For example, AI is already transforming industries—from data processing to client services. But AI’s dual nature requires careful leadership. It presents immense opportunities for innovation but also exposes vulnerabilities that malicious actors could exploit. Leaders need to balance these possibilities while ensuring robust defenses against misuse.
While technology may change, the core legal obligation to protect client information remains unchanged.
Effective communication and resilience are also key leadership traits. Communication isn’t just about speaking; it’s about listening to stakeholders, staying attuned to signals both inside and outside your organization, and engaging with diverse audiences. Resilience is more than bouncing back from setbacks—it’s about embracing challenges as opportunities for growth. That’s the mindset I strive to bring to my work and the culture I aim to cultivate in my teams.
Can you discuss some of the challenges you’ve faced and how you overcame them?
Leadership challenges vary widely, but two distinct categories stand out: crisis situations and large-scale, mission-critical initiatives. Both test a leader’s capabilities but require different approaches.
In crisis situations, leaders need to make swift, informed decisions and remain resolute once those decisions are made. Preparation and expertise are crucial, but in the heat of a crisis, leaders must act decisively and with purpose. During my time trading credit derivatives at JP Morgan in Tokyo during the 9/11 attacks, we had to respond to an unprecedented situation with limited information. Tokyo was the first market to open after the attacks, and our team had to act with urgency while being mindful of the human tragedy unfolding. That experience shaped my approach to decision-making in high-pressure situations.
A more recent challenge was leading the Pennsylvania Department of Banking and Securities through the banking crisis of 2023. Unlike a market crash, this involved managing the collapse of regional banks with significant systemic reach. In today’s digital age, information spreads
quickly, and leaders must be prepared to make fast, yet carefully considered decisions. Once a choice is made, it’s vital to remain steadfast and act with purpose.
Leading large-scale, mission-critical projects demands a different approach. These projects often focus on longterm goals, involve multiple stakeholders, and have broad industry implications. At Treasury, I led a team tasked with evaluating the U.S. financial regulatory framework. It was an intricate task that involved synthesizing policy considerations, managing diverse stakeholder interests, and maintaining clarity and focus throughout the process.
In 2013-2014, I worked on the regulatory examination of non-banks for systemic risk designation. The work was complex and required deep analysis and extensive coordination between industry stakeholders and regulators. Success in these kinds of initiatives hinges on understanding the full scope of the challenge, breaking it down into manageable tasks, and maintaining team motivation and focus.
How do you see the legal industry evolving in the next few years, and how can attorneys prepare for it?
We’re at a fascinating moment in time, with technology, particularly AI, fundamentally reshaping industries. As the Academic Director of the Executive Education AI Program at Penn Law, I’m working to prepare lawyers for this transformation.
Lawyers in industry-specific practices need to understand how AI will impact their sectors. For example, in healthcare, AI is revolutionizing diagnostics and treatment planning. In finance, it’s transforming everything from compliance reporting to trading strategies. It’s essential for lawyers to grasp not only what AI can do but also its limitations. AI can’t replace human judgment, and strategic, analytical decision-making will always require human expertise.
AI also presents new legal challenges. Issues like “hallucinations” (when AI models produce misleading results) and AI bias are already on the radar. As the law
evolves to address these issues, lawyers need to stay informed and engage with the technology. Liability is another critical area, especially as AI systems become more autonomous. Lawyers will need to rethink traditional concepts of liability to navigate these complexities.
Lastly, data governance and ethics will become increasingly important. While technology may change, the core legal obligation to protect client information remains unchanged. Lawyers must stay abreast of these developments and ensure they’re equipped to offer sound legal advice in an AI-driven world.
What’s your approach to developing and leading teams?
I’ve had the privilege of leading teams across diverse contexts, from large institutional teams to high-velocity environments like our accelerator program. While every team is unique, I’ve identified a few key principles that work across the board.
First, aligning team purpose with performance is critical. When everyone understands how their work fits into
broader strategic goals, it boosts focus and motivation. From the outset, it’s essential to establish this alignment.
Next, fostering a culture of accountability is vital. Trusting your team to take ownership of their work and decisions is crucial for high-functioning teams. While intuition is important, data-driven decisions are equally essential. Staying informed about how challenges are evolving helps boost team confidence and morale.
Recognizing that people are driven by different factors— whether it’s recognition, challenge, or stability—is also important. Tailoring your approach to individual motivations helps ensure sustained engagement. Finally, an outcomes-focused approach, paired with opportunities for growth, is key. Leaders should invest in team members’ development, matching them with learning opportunities and assignments that stretch their skills and broaden their perspectives.
Any final thoughts on career and leadership?
Looking back on my career, I’m incredibly grateful for the opportunities and challenges that have shaped my leadership journey. While the financial sector continues to evolve, some principles remain timeless: building trust, fostering meaningful relationships, and developing the next generation of leaders. I’m energized by the combination of technology and human judgment, and I truly believe that our greatest achievements come from uniting people to tackle complex challenges together.
She leads strategic initiatives across Wharton Finance and is Founder and CEO of Wharton Cypher Accelerator. Hammer is also Adjunct Professor at the University of Pennsylvania Law School and Affiliated Scholar at the Penn Program on Regulation. Previously, Hammer was Managing Director of the Center for Innovation in Finance and Senior Director of the Alternative Investments Program at Wharton.
EVAN WONG CHECKBOX.IO
Evan Wong, co-founder and CEO of Checkbox, discusses the important role of legal intake software in the quest for greater visibility and efficiency across legal workflows—including the benefits of dedicated “no-code” systems that allow legal teams to respond nimbly to an organization’s evolving needs.
CCBJ: Let’s talk about the history of legal organizations and technology. They’ve traditionally been wary of adopting new technology, due to concerns around disruption. But that may be changing. What shifts are you seeing that have made legal technology more appealing to in-house teams?
Evan Wong: One of the key drivers I’m seeing in the market is that the workload in-house teams are faced with tends to outpace the growth in headcount. While I think legal teams have historically been resistant to technology, I don’t think it’s any longer a choice. To produce more output and continue the turnaround times that legal teams pride themselves on, without having the headcount to do so, they must develop better processes—and at some point, that must involve technology. When you think about why that’s the case, there are macro trends.
When companies are growing, the amount of work that’s coming into legal is also growing. But like I said, the headcount probably isn’t scaling accordingly, so they need to find ways for every lawyer to be more productive. Regardless of the type of work—whether it’s reviewing contracts, registering trademarks, advising on potential M&A transactions, etc.—legal teams are starting to ask whether there are ways to use technology to increase that capacity. There’s pressure to be more efficient.
Legal teams have historically been seen as a cost center, but over time they’ve become more embedded in the enterprise. Many business processes involve legal. If the company is buying a product or service, at some point legal is involved. Or maybe there’s a labor dispute, or human resources dispute. Legal is involved.
With legal at the center of so many of today’s business processes, the general counsel has evolved from simply being the most senior lawyer to also having to be a business operator. Technology is such a key part of being able to run an efficient department—and legal is no different.
As we see more legal departments embracing technology at greater depth, how do you see them approaching their need for greater visibility into operations and workflows across the board?
There is definitely a strong desire at the moment for chief legal officers and general counsel to get more visibility into what’s coming into the legal department—who is working on what, where it’s coming from. Every function in the business has its control center, where they’re able to see workload and allocation of resources. In terms of legal, what they are looking at today is really this concept of legal intake.
But to get an understanding of what’s happening in the legal department, you need to somehow capture that data. Often that data problem—or that visibility problem—really starts as an intake problem. Before you have the data to even create the dashboards or generate the insights to make decisions around operations and resources, you first need to solve for your intake.
That’s where I’m really seeing legal teams embrace technology. In the past, intake had been a tricky area to apply technology to because there was fear about too much change being introduced to the business, especially in terms of getting people to go to a centralized “legal front door” where they’d have to fill out a form.
But technology has come a long way in being able to meet people where they are—in Slack, in Teams, in email, where people naturally come to legal already—and legal is now able to implement its own technology accordingly. Checkbox, for instance, which is a legal intake tool, is one of those technologies that lives in those existing enterprise tools, whether it’s the communication tools I just mentioned, or in tools like Salesforce for commercial teams, or in procurement tools for procurement teams.
The idea is to be able to automatically capture requests, triage them, categorize them and assign them for the legal team to work on—and then ultimately to have the dashboards and reporting capabilities to see exactly what is happening throughout the legal department.
While visibility is incredibly important to legal teams, so is efficiency. How do technologies like legal intake and artificial intelligence (AI) help organizations scale the impact of increased visibility without also increasing the workload?
You’re right, visibility isn’t the same thing as efficiency. In fact, when teams implement matter management or legal intake tools, they often find that while they now have the data to understand what’s coming in, it doesn’t necessarily help them do the work.
So, when we look at efficiency and creating more capacity, we also need to start looking at technologies that actually help lawyers do some of their work. Now, it’s not going to be all of the work. This is not a situation where AI and automation tools are replacing lawyers. It’s about replacing the low-value, high-volume work that lawyers frankly overqualified to do.
For example, self-service technologies can play a key part in creating capacity or improving efficiency in the context of contracting—such as with self-service nondisclosure agreements (NDAs). A lot of legal teams that work with Checkbox will completely automate their NDAs, so that it becomes what they call a “no-touch legal process.”
But it doesn’t have to be contracting. There are other use cases. It can also be regulatory. Or it can be around privacy, or conflicts of interest. We have customers that use AI chatbots to answer questions around gifts and entertainment and travel. Every organization has policies in these areas, and their legal teams are probably spending a lot of time answering a bunch of questions that someone should really just be able to read from policy. Training an AI chatbot to answer those questions as a first line of defense creates more time for the lawyers to spend on more important and
high-impact work. And when something comes up that the AI realizes is outside of the comfort zone of automation, it can escalate to getting an actual lawyer involved. Again, it’s not about removing the humans. It’s about reserving humans for more impactful and complex work.
Talk to us about whether legal teams really need dedicated systems and why they can’t—or maybe won’t— leverage existing enterprise level tools.
The reality is that, functionally speaking, legal teams can use existing enterprise or information technology (IT) tools. The nature of these tools is that they are designed to be enterprise-wide. However, just because you can doesn’t necessarily mean you should. I would say there are really three good reasons why legal teams should consider finding a dedicated legal system rather than using an IT one.
The first is that IT tools tend to be more transactional in nature than what legal really needs, which is relational. When we think about an IT ticketing system, often it’s about resolving a request involving not being able to sign in to your laptop, for instance—something like that. Now, that doesn’t require a lot of context. It doesn’t require
much of a relationship to get that solved. Compare that to legal counsel, where the relationship with the business, understanding the business context and being a trusted advisor are very important: The technology needs to reflect and enhance that relationship as opposed to degrading it.
The second reason involves ownership. Legal workflows tend to be more complex than IT workflows. They also tend to change a lot more than those in other parts in the business, because legal work is often a reaction to business changes or regulatory changes. As laws change, as regulations change, and as business grow into new areas, the ways that legal reacts and supports the business tend to change. It’s quite dynamic. So, the tools legal uses also need to be dynamic. If legal needs to submit a ticket to IT every time it needs to change a workflow, it’s going to be too slow. What legal needs is a system that the legal team owns and that it has control over and can customize easily.
Now, of course, the legal team is not going to consist of “tech people,” so often what that means is adopting what is known as a “no-code platform.” A no-code platform— which is what Checkbox provides—allows those custom workflows or pieces of software to be built without needing a developer, or an IT person, or even any coding background at all.
The third reason legal needs its own tools involves confidentiality or “legal privilege,” to use a legal phrase, because if you’re using an IT tool, its access controls often aren’t as robust as you’d need in a legal context. Legal teams deal with things like labor disputes, strategic projects, litigation, M&A transactions, etc., all of which should really stay within the legal department and maybe even be restricted to specific people who are working on those matters. But often the systems from IT aren’t designed to allow things to be privileged or confidential—especially if IT is managing the system, in which case they probably have access across all the data.
Like I said, legal teams can use enterprise and IT tools, functionally speaking. It’ll get them maybe 80 percent of the way there—but for those three key reasons, legal teams
Legal intake and workflow tools connect all of your people, processes, knowledge and systems—they are the interaction layer between your business users and the legal department.
often aren’t best suited to using IT tools in a practical sense. They would be better off using a dedicated legal tool. The challenge for legal departments, however, isn’t so much in knowing that they need to do that, but more so in convincing IT that it’s truly what they need.
We’ve talked about some of the new technologies out there and how they can help legal teams specifically. But still, when it comes to new technology, legal teams have traditionally been cautious about introducing too much change to their business. Have you seen this mindset shifting? Or is it more that people just see it as inevitable, given the macro trends you mentioned earlier, which are creating greater demands in terms of productivity and efficiency?
That mindset hasn’t necessarily shifted. There are still concerns around change management, but it’s important to recognize the ways in which today’s technology has reduced the risk of change management—or even the need for it.
One of the major reasons is the advent of generative AI. To use the example of legal intake again, previously you would have had to ask your business to completely change the way that they request help from legal. If you wanted people to stop sending emails or Slack messages to legal, for instance, they would have to be told, “Stop doing that. You now need to go to this bookmarked internet page, where you’re going to have to fill out a form with all these fields before we’re going to help you out.”
If you do that in an organization of thousands of people, it’s a tall task to get that many people to suddenly change the way that they approach legal, especially if it’s something
they only do occasionally. But this is an area where generative AI has made a big difference, since AI can now live in all those various areas of the business. AI can monitor Slack channels. It can live in Teams chats. It can live in email inboxes. And as requests come in, AI can automatically respond to them—and, if a lawyer is required, the AI is able to take the original conversation and extract the key information that’s required to either create a matter or generate a brief for a lawyer.
So, while the mindset hasn’t necessarily changed in terms of that fear of change, the new technology has dramatically reduced the friction—or even the nature of the change itself—so that legal teams are now able to roll out technology with more confidence.
Let’s talk about contract lifecycle management (CLM) tools, which tend to be widely adopted among most centers of an organization. Can legal departments just use CLMs as they have been doing to solve some parts of the visibility and efficiency issues they’re facing?
Yes, but not holistically. CLMs are powerful technologies that are great at handling the contract lifecycle. And with CLMs, you can definitely get visibility into your contracts and their data. You can gain efficiencies by providing selfservice for some of the contracting work that you’re doing or even just in terms of searching for things in your repository.
But CLMs, as the name suggests, are solely focused on contracts. There is a lot more to legal work than just contracts. Depending on your organization, contracts might make up anywhere from 40 percent to 60 percent of the work that the legal team does—but what do you do about the rest of it? To address visibility across the entire legal department and provide efficiencies for things beyond contracting, you’ll need other tools to complement your CLM technology.
There are really three fundamental pieces of technology that run legal departments. CLM is one of them, but there are also e-billing tools that handle interactions with outside counsel. And the third category is legal intake and workflow,
which we’ve been discussing. That’s the part that fills in the gaps and does the things that CLM and e-billing tools are not able to achieve. It’s the tool that connects all your people, processes, knowledge and systems—the interaction layer between your business users and the legal department.
As we see legal teams scale and adopt new tools, how important is it for these solutions to remain flexible and adaptable to the changing needs within the business?
Very important, because legal is a reactive function that has to be supportive of the business strategy and business environment. So, the tools and technologies that legal uses must also be adaptable and flexible, allowing the team to pivot as the organization grows into new products and new markets or as the external business environment changes. As I mentioned before, legal will often want to have a very flexible no-code tool, because they need to be able to react quickly.
If we think back to just a few years ago, for instance, when the world was flipped upside down by COVID-19, we had a legal team that used Checkbox and was therefore able to quickly build a workflow that allowed their frontline staff to rapidly communicate changes in supplier payment policy to all of its customers. They were able to roll that out in a single day, because of the flexibility and adaptability of the legal technology stack that they had.
Without a tool like that, it would be very difficult. Either you don’t have the tools at all and you’re just trying to create solutions with people, which is sometimes impractical. Or you’re relying on IT, which has many other priorities and often doesn’t really get around to addressing the needs that legal has on the technology front.
Looking ahead, what trends and/or innovations do you believe will most significantly shape the way in-house legal teams operate in the future?
The obvious answer is AI—it has so many applications in so many different areas of legal work. Even today, it’s already playing a big role in knowledge management. It is able to
consume an organization’s historical and institutional knowledge and use that information to speed up some of the requests that are coming into legal. It plays a critical role in removing a lot of the administrative and manual data entry work lawyers typically have had to do. We also see AI playing a role in invoice review for outside counsel. When someone sends in an invoice, AI can automatically read it and match it against the outside counsel guidelines to ensure that it’s compliant and flag it if not.
Beyond that, AI is able to impact not only the administrative aspects of legal work but also legal judgments around contract reviews. It’s able to look into an organization’s playbooks and previously agreed-upon contracts and then look at a new contract and flag where positions are different—maybe even auto redlining and suggesting changes as well.
These are just some examples. There are many more. The point is that AI is going to fundamentally change both the practice of law, which is the area of actual legal judgment and expertise, and also the business of law. If people fear AI—fearing, perhaps, disruption in their jobs— it’s important to keep in mind that AI doesn’t have to do the same work that lawyers are doing. It can just do the operational and administrative aspects, so that the lawyers can be lawyers. At Checkbox, that’s what we’re focusing on.
Evan Wong co-founded Checkbox in 2016 with James Han and Paul Wenck. At the age of seventeen, Evan founded Hero Education, an award winning education company that impacted thousands of to-be-adults. He then founded Sequoia-backed enterprise software company Checkbox (a $1B company in the making) and have helped many large enterprises empower their people to do more meaningful work through AI and automation.
SUE PELLEGRINO EVEREST DISCOVERY
CCBJ: How did you decide that this was where you wanted to be?
Sue Pellegrino: My husband Tom was in the litigation support space, running Copy Secure, a successful paper discovery company in Philadelphia. At the time, I was in the accounts payable department of a pharmaceutical company, and I would help him with his books as he grew. I loved looking at the whole financial statements of a small business instead of just seeing one line on the balance sheet of a big company. After surviving a series of mergers and their subsequent challenges, I finally said, “Okay, I’m done with corporate life. I’m out.”
I worked with Tom until he was at a point where it was time to move on or sell. He sold to a bigger outfit, which kept me on as the CFO for the transition. I stayed on until they decided to dissolve the business altogether. Then, an opportunity arose to acquire Everest Discovery, a provider of e-discovery and litigation support services. It had been in existence since 2005, primarily based out of Florham Park, NJ. The owner was a colleague of my husband, and he just called us one day and said, “I’m retiring. I bought a boat, and I’m moving to Alabama. I want you to take over the business. Put a team together and come up and meet me.”
So, we did that. I remember the call was in October, and we had our first meeting the Friday after Thanksgiving. Two weeks later, we had another meeting, and on December 31, 2017, at around 11 p.m., we signed the closing documents because the seller didn’t want to enter a new year for tax reasons.
Everest Discovery provides both electronic discovery and paper discovery services. The latter involves scanning documents, trial boards, exhibits, binders and preparation for attorneys. I knew that side of the business because that’s primarily what Tom did at Copy Secure. But the e-discovery side was a whole new world for me. I had no idea what I was doing, but I just said, “You got this,” and put my all into it
by delving into the computer technology world—reading, learning and reaching out to colleagues for help.
There were many ups and downs in the beginning, but the company has been on an upward trajectory for some time. Next year, it will celebrate its 20th birthday, and we have some exciting stuff coming up.
Talk to us about your communication style with your team.
I’m a talker—I’m Italian— so I talk regularly with my team. I prioritize having meaningful conversations. I hold monthly meetings with my management team, and an agenda is always sent out in advance, so it keeps the meetings organized, productive, and quick. We don’t want to be bogged down talking for hours and hours and hours. My operations team has a daily “scrum call”—a quick check-in to align with the day’s workload and see what everyone has on their plate.
Additionally, the sales team has weekly meetings to discuss potential leads, pipeline strategies, upcoming events, or just as a learning session. The topic du jour might be, “How did you handle this challenging client request?” or “How did you scope out a project? What were the steps you took?” Those conversations are happening more often. I feel these touchpoints are important to ensure everyone’s aligned with the company’s goals and has the opportunity to be heard and share updates.
We also have communication technology, SharePoint, to maintain our documentation and HubSpot for our CRM. We have a time tracker to record my operations team’s daily activities. But communication is about more than tools and meetings. Everybody talks about having an open-door policy, but it’s often mere lip service. I want to actively foster transparency, accessibility, and open dialogue with my team. Even though we work remotely and there’s no real door to knock on, I encourage my team to text, call or shoot me an email when they need some time with me. I want everyone to feel they have a safe space to express their concerns or share their ideas.
I don’t want people to be like, “Oh my gosh. She’s the president of the company. I can’t call her.” I want communication to be open and honest. I also believe in active listening so that expectations from both ends are clear.
How do you work with your team to analyze risks and make major decisions for the organization?
I’ve always approached analyzing risks with a balance of data and instinct. I can overanalyze things, which then delays my decision or hinders progress moving forward, so I sometimes just go with my gut. That is an indicator to dig deeper because when something doesn’t feel right, that’s my sign to step back, analyze the situation, reflect on past experiences, look at the current reality, and then try to move forward. I also put pen to paper, weighing the pros and cons, literally writing them down. Occasionally, I’ve used methods like SWOT analysis, such as when I decided to acquire Everest in ‘17. I needed to write out a straightforward list of pros and cons and see the bigger picture. SWOT analysis provided a framework for assessing internal and external factors as well as current and future potential.
The other thing I don’t do is make decisions alone. I consult with my management team, particularly if it concerns significant changes such as adding team members, working with outside resources, or fostering our company culture. It’s a group effort. For anything technical, I turn to my operations team for input. When it comes to risks, I like to hit them head-on and do so immediately so we can keep our goals on track because ignoring risks will make it harder to manage them later. Once I have clarity and we develop a strategy, we can implement controls, policies and procedures and continue to monitor those risks. This approach has proven to be effective over time.
How do you define success, and what role does company culture play in achieving that?
Positive team culture starts with our core values of respect, kindness and teamwork. These are intertwined with everything we do at Everest on a daily basis. Recognition also plays a huge role in maintaining a positive environment. Because you don’t want someone to sit there and be like, “Oh, man, I went above and beyond but it doesn’t seem like anyone recognized it.” I’m a big believer
in saying thank you. Just those words can go a long way. And when a team member achieves something significant, like earning an industry certification or completing a major initiative within Everest, we celebrate them—monetarily and sometimes even publicly. For example, one of our newer team members passed the Relativity Certified Administrator exam within eight months of joining us. It’s a difficult exam and he didn’t have much industry experience. We rewarded him with a bonus and shared a nice memo company-wide. The ensuing emails from his colleagues, “That’s awesome,” “Great job,” etc., still make me smile.
Our team is remote and across different states, so we work hard to stay connected. As I mentioned, we hold regular virtual meetings, but we also bring everyone in for faceto-face contact. This past summer, we flew in everybody who’s not in Pennsylvania for three days of working group meetings and employee-appreciation events, including a Phillies game and a nice dinner. It was the first time that some of the team members met each other in person. I loved seeing the camaraderie. After the out-of-towners took off for the airport, but before boarding their flights, I received emails and text messages saying, “That was fantastic,” and “You can tell how much effort you put into organizing everything.”
When challenges or conflicts arise—which are very few, I have to say—I am very blessed to have the team that we have and that everyone works so well with each other. Everyone knows they can come to me or any member of management with concerns. We’ll discuss them. We’ll support each other. We’ll collaborate to find solutions. It’s not about the titles; I’ve never been about titles. I don’t even like being called president or owner. I want my team to know I’m a team member too. I think that mutual respect keeps us strong.
You mentioned the certification and I’m interested in knowing more about how you support your employees’ professional development.
I’m a big believer in having a plan for each person. We recently completed year-end performance reviews, and in each of the reviews, we ended with, “Okay, here’s what you
need to get to the next step, and here’s the support you’ll receive from us. So, supporting professional development is key for me. We start by having those conversations about their own development goals, and then, based on their role, we explore the programs or other next steps. I like to provide employees with both the time and the resources to achieve their goals, whether that’s allowing time during the workday for studying or offering financial incentives to pursue certifications. Our hosting providers offer certifications, so they’re tied directly to their roles, and I’m always encouraging participation in such certifications and making training as accessible as possible. Again, we further motivate the team to pursue these opportunities for professional development through bonuses and other incentives.
We also have a set of metrics based on various aspects of a team member’s operational performance, such as problemsolving abilities, communication skills and willingness to take on more responsibility. That helps me determine whether they’re ready to take on more responsibility. Mentoring is another aspect. While my management team and I like to think of ourselves as equals to any staff members, we also make ourselves available to help them with any tools or resources they may need. Listening to their goals and offering a clear development path helps keep them engaged, which also helps us achieve our long-term goals as a company.
From restoring classic cars to serving as an accounting executive and entrepreneur in e-discovery, Sue Pellegrino has challenged the status quo around what a woman leader can be her whole life. Sue has spent her career managing organizations’ finances, ranging from publicly traded companies to regional enterprises and small businesses. Now, she runs Everest Discovery, taking the business to new heights.
RICHARD TORRENZANO & STUART R. LEVINE THE TORRENZANO GROUP
The question is no longer just about risk mitigation—it’s if leadership can adapt fast enough to thrive, or risk not only liability but extinction.
The next two to three years will radically redefine “high stakes” and risk for boards and CEOs as sprouting challenges driven by artificial intelligence (AI), cybersecurity and stakeholder communications escalate and demand more than traditional action and oversight.
Board legal advisors will no longer merely focus on how to mitigate risks; they will guide organizations through AI’s uncharted territory, where business decisions increasingly intersect with emerging domestic and international regulations, as well as ethical complexities, coupled with heightened immediacy.
As domestic and international laws evolve, legal teams must proactively stay ahead, anticipating changes and ensuring strategies align with compliance, innovation and regulation. Lawyers should see this as an opportunity to participate in various trade association legislative initiatives.
The development and use of AI is evolving at ludicrous velocity, becoming a thrusting force behind technological change. Traditional leadership priorities—profit margins and operational efficiency—must now coexist with a complex array of new technology challenges that demand immediate understanding and faster decision making.
Concerns are not abstract—they are already at the boardroom table.
AI is reshaping business and governments in ways that require a sophisticated understanding of new potential liability, compliance requirements and increased regulatory oversight emerging with AI. Business leaders will increasingly rely on legal advisors to navigate this uncharted territory.
The question is no longer just about risk mitigation—it’s if
leadership can adapt fast enough to thrive, or risk not only liability but extinction.
As Peter Drucker famously stated, “The greatest danger in times of turbulence is not the turbulence—it is to act with yesterday’s logic.”
Therefore, to stay ahead, counsel must guide boards and leaders through six key critical challenges that will redefine risk management, governance and legal strategies in today’s global business and financial markets.
Embedding AI: Negotiating legal loopholes without tripping over algorithms
AI’s potential extends far beyond operational efficiency, with strategic implications that corporate counsel must understand and address. Last quarter, 36 percent of S&P 500 companies mentioned AI in earnings calls, but only 13 percent of them have AI expertise on their boards
Boards must engage experienced advisors to elevate AI literacy, ensuring it’s treated as a strategic asset rather than just a tool.
Tip for Success: Push boards to adopt an AI governance framework, including an AI Code of Conduct , and structure capital deployment strategies through a legal lens.
Meltdown to mellow: Navigating legal shields in the age of viral oops
In this digital arena, reputation is not just a stakeholder communications issue—it’s a legal one.
Counsel should ensure companies treat reputation as a strategic asset underpinned by strong legal safeguards. Data breaches, ESG failures and privacy violations are not just business risks—they lead directly to liability and public nightmares.
Fast, authentic communication is key to managing reputational damage. Slow responses laced with
legalese or jargon create additional risks. Corporate social responsibility (CSR) initiatives should be backed by measurable, legally sound commitments to avoid litigation.
Tip for Success: Help create a strategy that ensures fast, transparent and accurate communication to protect operations, revenue and reputation that addresses all stakeholders. Work closely with communications professionals to align messaging with legal obligations and participate in scenario-based crisis training sessions.
Shareholders to stakeholders: New rules of success
The shift toward stakeholder capitalism means boards and CEOs must consider a broader set of interests beyond shareholders.
Corporate counsel now face the challenges of adapting and evolving AI regulations while managing rising stakeholder expectations.
As laws develop, legal teams must ensure compliance and ethical alignment, shaping strategies that not only foster
innovation but also meet the demands of employees, customers and regulators.
Tip for Success: Develop a stakeholder engagement strategy that aligns with legal obligations and supports transparent communications. Ensure leadership is well-versed in how stakeholder capitalism affects corporate governance and review the legal frameworks guiding these interactions.
Digital gold rush: transform without leaving doors open for cybercriminals
The SEC’s 2023 cybersecurity rules mandate greater cybersecurity transparency and risk management, governance and incident reporting.
This creates a significant new area of responsibility for corporate counsel, who must ensure the company complies with regulations and discloses material cybersecurity incidents accurately and on a timely basis.
With new SEC Regulations, cybersecurity is no longer an afterthought—it must be integrated into a digital
transformation strategy. Counsel should work to conduct regular audits, ensure robust incident response plans and align digital growth with evolving legal standards on cybersecurity.
Tip for Success: Advise on the creation of a legally sound incident response plan that satisfies SEC requirements. Ensure board members are regularly briefed on cybersecurity risks and integrate AI-driven threat detection strategies to mitigate legal exposure.
How agile and inclusive cultures are shaping tomorrow’s legal landscape
Rigid hierarchies can’t keep pace with today’s fast paced global markets.
Leadership must adopt inclusive practices, and legal counsel ensures these frameworks comply with current and emerging regulations. Counsel plays a key role in preventing governance failures.
Inclusion is both a strategic and legal necessity, driving innovation while ensuring compliance with diversity and anti-discrimination laws.
Tip for Success: Establish governance processes that are not only legally compliant but help to drive strategic initiatives that exceed legal standards while keeping the company competitive.
From remote to robots: navigating new workplace frontier
As companies expand remote work and automation, corporate counsel must navigate the legal intricacies of this workforce transformation.
Strategies need to adjust emerging labor laws, reflecting the impact of automation on jobs…and evolve with new workforce expectations. While current regulations cover employee reductions, no laws yet address liability for replacing humans with robots or AI.
Remote work introduces new challenges in workplace privacy, intellectual property, and employee surveillance— all are rapidly evolving.
Upskilling and reskilling programs are crucial to retaining a competitive workforce while ensuring hybrid models comply with employment laws.
Tip for Success: Guide leadership through legal complexities of remote work and automation, ensuring compliance with emerging labor laws and creating forward-thinking workforce policies that minimize risk.
“What we do in life echoes in eternity.” – Maximus, Gladiator
Companies and boards that stick to outdated approaches will fall behind. Lead decisively through complex challenges, ensuring compliance, resilience, and long-term success.
helps organizations take control of how they are perceived. For nearly a decade, he was a member of the New York Stock Exchange management (policy) and Executive (operations) committees. His new book was released in August: CEO Playbook: 101 AI and Communications Game-Changing Stakeholder Strategies
He has served on fifteen boards and continues to counsel CEOs across multiple industries. He focuses on governance and board assessments, organizational culture, strategic planning/communication and transactions. He is a bestselling author, including The Six Fundamentals of Success and Cut to the Chase… and was CEO of Dale Carnegie & Associates
HQ: Cocoa, FL
# of Employees: 22 Total Raised: $0.35M
Institutional Investors:
Beresford Ventures
Activat voicescript.ai/
Description:
2.34x
MEDIAN
SIZE MULTIPLE
Developer of court reporting software designed to modernize the court reporting industry and legal industries. The company’s software offers separate audio recording channels with optimized recording functionality for remote videoconferencing, video recording capabilities, reporter annotation features with simple-to-use UI, and customizable hotkey functionality, enabling digital reporters to deliver rough draft transcripts immediately after a proceeding and real-time streaming transcripts with readbacks as well as playback options during a proceeding.
The company raised venture funding in a deal led by Beresford Ventures on November 1, 2023. Other undisclosed investors also participated in the round.
Source: Pitchbook (As of August 2024)
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