LawNext

Five years ago, Noah Waisberg sold Kira Systems, the pioneering AI contract-analysis company he co-founded, to Litera. Even though the deal itself went well, the experience of going through the sale was hard, Waisberg now says. But that experience provided the fuel that turned into his next business. As part of the sale, he kept a copy of the underlying Kira technology and about 30 of the company's roughly 180 employees, and used them to launch Zuva.

Zuva started as an API-only company, but it has since turned its focus to the sell side of M&A. After interviewing some 200 dealmakers about the most painful parts of selling a business, Zuva built software to help sellers manage the flood of bidder questions. It also launched a tech-enabled diligence service that pairs Kira's AI with experienced former Big Law associates. Zuva says the service delivers work product comparable to Big Law at a fraction of the cost.

Waisberg was last on LawNext in 2021, marking the 10th anniversary of Kira and the release of his book, AI for Lawyers. In today's episode, he and host Bob Ambrogi discuss Zuva's new direction and what the recent expiration of his post-sale restrictions means for the company. They recorded this conversation on the day Harvey announced its latest mega-funding round, so they also talk about the prospects for Harvey and Legora against the frontier labs, and why Waisberg recently remarked that we've hit "peak legal tech." He also covers the limitations of today's AI that he thinks the market underestimates, and why the billable hour remains the biggest obstacle to efficiency tech.

Thank You To Our Sponsors

This episode of LawNext is generously made possible by our sponsors. We appreciate their support and hope you will check them out.

• Paradigm, home to the practice management platforms PracticePanther, Bill4Time, MerusCase and LollyLaw; the e-payments platform Headnote; and the legal accounting software TrustBooks.

• Briefpoint, eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner).

• CosmoLex, helping law firms manage their entire practice in one platform, from intake to payment. Try it free.

• Ajax, the AI timekeeper lawyers want to use.

If you enjoy listening to LawNext, please leave us a review wherever you listen to podcasts.

Chapters:

(00:00) Introduction

(03:16) From Kira to Zuva

(09:49) Why Selling a Business Is Hard

(17:00) Zuva's Sell-Side Strategy

(35:27) The Legal AI Market

(51:52) AI's Limits and the Billable Hour

(58:25) The Case for Selling Your Business

Legal tech company Clio has long said that its mission is to transform the legal experience for all. Until now, that "all" has largely focused on law firms and their clients, but recently Clio announced a major initiative to develop technology for the judiciary.

As part of that initiative, it hired Pablo Arredondo, the former cofounder of Casetext and developer of CoCounsel, one of the first AI legal assistants, to lead product development. Arredondo was on this show on Sept. 1 to discuss his new role.

Now, Clio has made another major hire to help lead this project: Bridget Mary McCormack, the innovative former chief justice of the Michigan Supreme Court and current president and CEO of the American Arbitration Association, who will join Clio in October as general manager, judiciary, to lead the market and commercial strategy for the judiciary business.

On the day her hiring was announced, McCormack sat down with host Bob Ambrogi to discuss why she considered this an offer she could not turn down and how she believes she, Arredondo, and Clio can transform the legal experience for the judiciary.

Thank You To Our Sponsors

This episode of LawNext is generously made possible by our sponsors. We appreciate their support and hope you will check them out.

• Paradigm, home to the practice management platforms PracticePanther, Bill4Time, MerusCase and LollyLaw; the e-payments platform Headnote; and the legal accounting software TrustBooks.

• Briefpoint, eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner).

• CosmoLex, helping law firms manage their entire practice in one platform, from intake to payment. Try it free.

• Ajax, the AI timekeeper lawyers want to use.

Chapters:

(00:00) Introductions (02:49) Bridget McCormick's New Role at Clio (08:44) Co-Designing Technology with Judges (11:11) Building Tech for the Judiciary vs. Law Firms (15:35) Addressing Court Challenges with Technology (20:28) Bottlenecks in the Court System (23:30) Improving Existing Court Technologies (25:20) Integrating Technology in Courts (28:00) The Role of AI in Judicial Processes (32:02) Addressing Self-Represented Litigants (35:50) Balancing Tradition and Innovation in Courts (40:20) Setting Goals for the Future of Court Technology

If you enjoy listening to LawNext, please leave us a review wherever you listen to podcasts.

Call it Alex Su, redux. We do not usually have the same guest on LawNext twice in the same year, but there is good reason to have Alex back, as he has just been named president of Latitude Legal, the flexible legal staffing company.

Last February, Alex and host Bob Ambrogi recorded a live episode of this podcast over lunch in a Cambodian restaurant in Alex's hometown of Alameda, Calif., as part of our LawNext on Location series. They talked about his winding career, from Sullivan & Cromwell associate to federal clerkship to legal tech startups and finally to chief revenue officer at Latitude.

In that interview, Bob asked Alex what was coming next. His answer was that as AI got better, the demand for lawyers with real judgment — to direct it, check it, and own the work — would only grow. Seven months later, that prediction is proving prescient. In just the first half of this year, Latitude says it has seen a 52 percent jump in new law firm and corporate clients.

So with Latitude's promotion of Su to president, he returns to LawNext to discuss why he thinks AI is driving more demand for experienced lawyers, not less. He also talks about how Latitude's client-service model relies on former law firm partners and senior in-house counsel, why he pushes back on labeling flex talent as "contract attorneys" or calling Latitude an ALSP, and why he expects the market for flexible legal talent to keep expanding as law firms and legal departments sort out what AI can and cannot handle.

Thank You To Our Sponsors

This episode of LawNext is generously made possible by our sponsors. We appreciate their support and hope you will check them out.

• Paradigm, home to the practice management platforms PracticePanther, Bill4Time, MerusCase and LollyLaw; the e-payments platform Headnote; and the legal accounting software TrustBooks.

• Briefpoint, eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner).

• CosmoLex, helping law firms manage their entire practice in one platform, from intake to payment. Try it free.

• Ajax, the AI timekeeper lawyers want to use.

If you enjoy listening to LawNext, please leave us a review wherever you listen to podcasts.

Chronologies have become one of legal tech's hottest categories, with a wave of AI startups promising to turn a messy evidentiary record into a structured timeline in minutes. Jeff Kerr and his company Casefleet were more than a decade ahead of the pack.

Kerr finished law school in 2010 and made what he calls the crazy decision to start a law firm as his first job after graduating. Running an employment practice, he found that winning cases came down to knowing the chronology cold. But the only tools for building one were a Word document and a lot of patience. So he taught himself to code, left practice in 2015, and founded Casefleet.

On this episode of LawNext, Kerr joins host Bob Ambrogi to discuss what a decade of building fact-management software looks like now that AI has arrived. Last month, Casefleet launched Casey, a conversational AI agent that proposes facts, links them to legal issues, and drafts documents — with a citation engine that rejects any citation not matching the exact text of the underlying document.

Kerr deliberately draws a hard line on what he will let his AI do. Casefleet's agent is fully agentic in the sense of researching and iterating on its own, he says, but it stays read-only – it will not send emails, make calls, or file anything.

Among the other topics they cover:

• Why Casefleet's pre-AI data model turned out to be the right foundation for AI, and why classic Casefleet still runs alongside Casey.

• The company's move back toward e-discovery, including newly added document production, and why Kerr isn't chasing terabyte-scale cases.

• What happens to specialized litigation tools if the frontier AI labs push further into legal.

• Why Casefleet, profitable since 2018 and largely bootstrapped, may raise outside capital in the coming year.

Thank You To Our Sponsors

This episode of LawNext is generously made possible by our sponsors. We appreciate their support and hope you will check them out.

• Paradigm, home to the practice management platforms PracticePanther, Bill4Time, MerusCase and LollyLaw; the e-payments platform Headnote; and the legal accounting software TrustBooks.

• Briefpoint, eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner).

• CosmoLex, helping law firms manage their entire practice in one platform, from intake to payment. Try it free.

• Ajax, the AI timekeeper lawyers want to use.

If you enjoy listening to LawNext, please leave us a review wherever you listen to podcasts.

Pablo Arredondo, the Casetext cofounder who helped build some of the earliest and most influential applications of AI in legal practice, is joining Clio as senior vice president, judiciary, where he will lead the company's strategy for extending its technology into the courts. In this episode, recorded just ahead of the announcement, Arredondo tells host Bob Ambrogi why he is turning his attention to the judiciary — and why he believes the challenge starts with the sheer torrent of material flooding into the courts. "On Monday, somewhere on the order of three billion tokens are going to hit court dockets," he says.

Arredondo cofounded Casetext in 2013 and helped develop CARA, the first brief analyzer, and CoCounsel, the product that brought generative AI into everyday legal workflows. After Thomson Reuters acquired Casetext for $650 million in 2023, he joined that company, leaving at the end of last year. In this conversation, he traces how his interest shifted toward the courts — from watching judges organically adopt Casetext's Parallel Search to a recent project at Cornell's Legal Information Institute using LLMs to annotate the U.S. Code of Conduct for Judges with centuries of judicial ethics thinking from rabbinic, Islamic and Roman Catholic traditions.

Arredondo also explains why courts need "judiciary grade" technology rather than tools built for lawyers, how AI is driving a surge in pro se filings, whether AI could ever replace judges (his short answer: "absolutely not"), and where he plans to start when he officially begins the role Aug. 31. This is Arredondo's second appearance on LawNext this year, following a February conversation at his home in Tiburon, Calif., about his career and what would come next. Now we know.

Thank You To Our Sponsors

This episode of LawNext is generously made possible by our sponsors. We appreciate their support and hope you will check them out.

• Paradigm, home to the practice management platforms PracticePanther, Bill4Time, MerusCase and LollyLaw; the e-payments platform Headnote; and the legal accounting software TrustBooks.

• Briefpoint, eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner).

• CosmoLex, helping law firms manage their entire practice in one platform, from intake to payment. Try it free.

• Ajax, the AI timekeeper lawyers want to use.

If you enjoy listening to LawNext, please leave us a review wherever you listen to podcasts.

This week, LexisNexis announced the opening of its Customer Innovation Lab in New York City — a physical space where legal professionals, LexisNexis engineers, and AI companies such as OpenAI and Amazon Web Services sit in the same room and build legal AI together, in real time.

The company is calling it a new model for how legal AI gets built and shipped: Instead of developing products internally and asking customers to validate them afterward, customers bring their pain points into the lab, engineers code against them on the spot, and prototypes that pass muster can move into Lexis+ with Protégé in a matter of weeks.

Our guest today is the person leading that effort: Greg Dickason, chief technology officer of LexisNexis Legal & Professional. Dickason joined LexisNexis in 2019 and previously ran the company's Asia-Pacific business, where he launched Lexis+ AI in that region. Before LexisNexis, he was chief technology officer at CoreLogic.

In a conversation with host Bob Ambrogi recorded just ahead of the launch, Dickason explains what actually happens inside the lab as engineers code live alongside customers, and how this differs from the customer input LexisNexis has always said drives its product development. They also discuss what has already come out of the lab, including a multimedia Protégé Vault that lets a lawyer query a video deposition; why legal drafting is the lab's first priority; and how Dickason sees agents reshaping legal work.

Thank You To Our Sponsors

This episode of LawNext is generously made possible by our sponsors. We appreciate their support and hope you will check them out.

• Paradigm, home to the practice management platforms PracticePanther, Bill4Time, MerusCase and LollyLaw; the e-payments platform Headnote; and the legal accounting software TrustBooks.

• Briefpoint, eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner).

• CosmoLex, helping law firms manage their entire practice in one platform, from intake to payment. Try it free.

• Ajax, the AI timekeeper lawyers want to use.

If you enjoy listening to LawNext, please leave us a review wherever you listen to podcasts.

SurePoint Technologies, a company that provides practice-management, finance and growth technology products for mid-sized law firms, named Jeff Steinberg its chief executive officer on July 23, elevating Eric Thurston, who had led the company since 2023, to executive chairman. Two weeks into the job, Steinberg joins LawNext to speak with host Bob Ambrogi about what his appointment means for the company's customers.

His answer to that question is direct: This is a mandate for change, not business as usual. Steinberg is candid that SurePoint still has integration work ahead of it after acquiring four companies in four years — Coyote Analytics and ContactEase in 2022, Leopard Solutions in 2024, and ZenCase in 2025 — and he says the company will keep looking at acquisitions while it does that work.

Steinberg is no stranger to legal technology. He founded Redwood Analytics in 2000, an early innovator in helping law firms use their own data to understand their profitability, and sold the company to LexisNexis in 2008 (which then sold it to Aderant in 2014). He spent the years since in medical records retrieval for litigation and in other sectors, and served as a senior advisor to Aquiline Capital Partners, the private equity firm backing SurePoint. He arrives at a company whose roots go back to 1982.

Among the topics Jeff discusses:

• Why he distinguishes between machine learning and generative AI when it comes to developing systems firms need to trust completely.

• What he is hearing in his early conversations with customers about AI adoption.

• How SurePoint decides whether to build, buy, or partner.

• Why he thinks the mid-sized firm market has proven more resilient than many had predicted.

• The three priorities he has set for his first year.

For an interview with outgoing CEO Thurston, see: On LawNext: SurePoint CEO Eric Thurston on Acquiring ZenCase and His Vision for Mid-Market Practice Management.

Thank You To Our Sponsors

This episode of LawNext is generously made possible by our sponsors. We appreciate their support and hope you will check them out.

• Paradigm, home to the practice management platforms PracticePanther, Bill4Time, MerusCase and LollyLaw; the e-payments platform Headnote; and the legal accounting software TrustBooks.

• Briefpoint, eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner).

• CosmoLex, helping law firms manage their entire practice in one platform, from intake to payment. Try it free.

• Ajax, the AI timekeeper lawyers want to use.

If you enjoy listening to LawNext, please leave us a review wherever you listen to podcasts.

As chief technology officer at Casetext, Ryan Walker helped build CoCounsel, one of the first and most consequential generative AI legal assistants — a product so significant it led to the company's $650 million acquisition by Thomson Reuters. But Walker came away unsatisfied. Although the legal tech tools kept getting better, he believed, clients were seeing no benefit. Billing rates kept climbing and the efficiency gains never reached them.

That spurred him to pivot from building products to forming a practice — General Legal, an AI-native law firm he cofounded and leads as CEO, built on the premise that the fastest path to transforming legal services is not retrofitting AI onto traditional firms, but rebuilding the law firm from the ground up on an AI-forward foundation. Just six months out of Y Combinator, the firm has some 400 clients, a newly launched venture financing practice, and, in what may be a first for a law firm, an MCP server that lets clients' AI agents engage the firm directly.

In this episode of LawNext, Walker — not a lawyer but a PhD mathematician — tells host Bob Ambrogi why he believes AI can now automate 95% of routine legal work, how the management services organization structure allows an investable technology company to operate alongside a law firm, and why an AI-native firm paradoxically depends on hiring highly experienced lawyers rather than supercharging junior ones. He also explains the "second brain" approach that lets the firm's work product reflect each client's strategy, what earlier failed innovators like Atrium and Clearspire got wrong, and why he thinks the real reckoning will come when major clients simply refuse to pay for work AI can do.

Walker cofounded the firm along with two other Casetext colleagues, Javed Qadrud-Din, who was head of AI at Casetext and is now General Legal's chief technology officer, and J.P. Mohler, who was an LLM engineer at Casetext and is now chief product officer and managing partner. Their ultimate ambition, Walker says, is to make General Legal the biggest provider of legal services in the world and, along the way, to break the scarcity model that keeps legal help out of reach for the people and companies who need it.

Thank You To Our Sponsors

This episode of LawNext is generously made possible by our sponsors. We appreciate their support and hope you will check them out.

• Paradigm, home to the practice management platforms PracticePanther, Bill4Time, MerusCase and LollyLaw; the e-payments platform Headnote; and the legal accounting software TrustBooks.

• Briefpoint, eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner).

• CosmoLex, helping law firms manage their entire practice in one platform, from intake to payment. Try it free.

• Ajax, the AI timekeeper lawyers want to use.

If you enjoy listening to LawNext, please leave us a review wherever you listen to podcasts.

Martin Luther King famously said, "The arc of the moral universe is long, but it bends toward justice." My guest today quoted his words in her 2024 book, Law Democratized: A Blueprint for Solving the Justice Crisis. But now, two years after that book's publication — at a moment when many see the rule of law under strain and speak openly of democratic backsliding — it is fair to ask: Are we still arcing toward justice?

That is the question LawNext host Bob Ambrogi put to Renee Knake Jefferson at the start of today's conversation. Jefferson is a professor of law and the Joanne and Larry Doherty Chair in Legal Ethics at the University of Houston Law Center, and her work sits at the intersection of legal ethics, judicial ethics, lawyer regulation, legal education and access to justice.

She is also the coauthor of the acclaimed book Shortlisted: Women in the Shadows of the Supreme Court, an elected member of the American Law Institute, and a former co-reporter for the ABA Commission on the Future of Legal Services. In 2013, the ABA Journal named her a Legal Rebel for co-founding the ReInvent Law Laboratory at Michigan State together with Daniel Martin Katz. More recently, she was elected to the American Bar Association's Council for the Section on Legal Education and Admission to the Bar, the body responsible for accrediting J.D. programs — so, as she puts it, she's gone from offering constructive criticism from the outside to working on the inside

In her "spare time" (as if she possibly has any), she writes the Substack newsletter Legal Ethics Roundup, a weekly review of all things related to legal and judicial ethics.

In today's conversation, Renee and Bob talk in depth about the access to justice crisis and what can be done to narrow the justice gap, including why the biggest barrier to legal help may be that people do not even recognize they have a legal problem. They also discuss the promise and peril of AI as a tool for closing the justice gap, why regulatory reform has not produced the domino effect many once predicted, and what lawyers, law schools, regulators and innovators can each do to move the needle.

Spoiler alert: Jefferson remains a glass-half-full optimist — and by the end of this conversation, you may be too.

Thank You To Our Sponsors

This episode of LawNext is generously made possible by our sponsors. We appreciate their support and hope you will check them out.

• Paradigm, home to the practice management platforms PracticePanther, Bill4Time, MerusCase and LollyLaw; the e-payments platform Headnote; and the legal accounting software TrustBooks.

• Briefpoint, eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner).

• CosmoLex, helping law firms manage their entire practice in one platform, from intake to payment. Try it free.

• Ajax, the AI timekeeper lawyers want to use.

If you enjoy listening to LawNext, please leave us a review wherever you listen to podcasts.

When Anthropic launched Claude for Legal in May – more than 20 MCP connectors and a dozen practice-area plugins built specifically for legal work – it marked the company's biggest and most explicit commitment yet to the legal industry. It also reignited a debate that's been simmering since Anthropic's first legal plugin briefly rattled the stock prices of Thomson Reuters, RELX and Wolters Kluwer back in January: Is Anthropic's entry into the legal market a major step forward for legal productivity? Or is it a threat to trust, governance and the existing legal-tech infrastructure?

In today's episode, Mark Pike, associate general counsel at Anthropic and product lead for Claude for Legal, joins host Bob Ambrogi to share the inside story of Claude for Legal and his own unconventional path into leading its development. Pike, who went from Facebook to Slack to building internal tools for Anthropic's own legal team, talks about how that work turned into a product that has ignited both excitement and concern throughout the global legal industry. Among the topics they discuss:

• Why Anthropic decided legal deserved its own dedicated launch, and why now.

• What plugins, skills, connectors, cookbooks and agents actually mean in plain English.

• Why lawyers have become Claude's most active power users.

• Anthropic's decision to partner, rather than compete, with major legal tech vendors such as Thomson Reuters.

• How Anthropic thinks about human oversight and professional responsibility.

• Confidentiality, data training policies, and what firms need to know before adopting these tools.

• Anthropic's commitment to access to justice.

• What Claude for Legal might look like a year from now.

Whether you're excited about what this technology could mean for legal innovation, wary of what it means for the future of legal work, or just have questions about how it all works, this conversation offers insights.

Background links:

• Announcement: Claude for the Legal Industry.

• Webinar: How Legal Teams Put Claude to Work.

• Claude for Legal Github Repo.

• LawSites: Anthropic Goes All-In on Legal, Releasing More Than 20 Connectors and 12 Practice-Area Plugins for Claude.

Thank You To Our Sponsors

This episode of LawNext is generously made possible by our sponsors. We appreciate their support and hope you will check them out.

• Paradigm, home to the practice management platforms PracticePanther, Bill4Time, MerusCase and LollyLaw; the e-payments platform Headnote; and the legal accounting software TrustBooks.

• Briefpoint, eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner).

• CosmoLex, helping law firms manage their entire practice in one platform, from intake to payment. Try it free.

If you enjoy listening to LawNext, please leave us a review wherever you listen to podcasts.