Explore every episode of the podcast Reinventing Professionals

I spoke with Richard Tromans, founder of Tromans Consulting and Artificial Lawyer, which is the co-producer of the Legal Innovators Conference Series, including  Legal Innovators California in San Francisco on June 11th and 12th. We discussed the genesis of Artificial Lawyer, the inspiration for the Legal Innovators Conference, the importance of facilitating complementary conversations for law firm and legal department leaders, and best practices for balancing discussions of the practical and the promising aspects of emerging technology.

I spoke with Tom Chapman, the Co-Founder of Iceberg, a specialist recruitment firm focused on cybersecurity and e-discovery. We discussed how the demand for cybersecurity and e-discovery talent has evolved, the challenges companies face when hiring for these roles, and how AI and automation are impacting hiring in cybersecurity and e-discovery.

I spoke with Rick Campbell, the Executive Chairman and CEO of @GROUP, and Matt Winlaw, the CEO and Managing Director of @ID, one of three divisions that includes @DOCS and @SOFT, within @GROUP. We discussed open-source intelligence, why OSINT has become vital to modern legal operations, the blind spots in traditional legal risk models, predictive behavioral AI use cases, and practical ways for legal teams to integrate AI and OSINT without overwhelming their workflows.

In this 41st episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed value-based billing, driving firmwide innovation, and cultivating a willingness to be engaged.

I was lucky to have many great conversations with industry leaders at the 2025 CLOC (Corporate Legal Operations Consortium) Global Institute, which I captured in this #ReinventingProfessionals #Mixtape 😀 Thanks to the following participants for sharing their insights: 🎙️ David Blazejewski (David Blaze), Chief Revenue Officer, TruthOrLie.ai 🎙️ Tim Brady, CEO, Colligo 🎙️ Laurie Ehrlich (she/her), Chief Legal Officer, Dioptra 🎙️ James Ferguson-Mahan, Enterprise Account Executive, DeepL 🎙️ Kathleen Hoffman, Account Executive, LegalMation 🎙️ Austin Holian, Director of Marketing and Partnerships, Clarra 🎙️ Sam Kidd, CEO, LawVu 🎙️ Bryan Kimes, Director of Legal Operations and Litigation Support, Philip Morris International 🎙️ Jessica King, Vice President of Legal Innovation and Strategic Partnerships, ContractPodAi 🎙️ Henal Patel, CEO, DocJuris 🎙️ Charles Post, Executive Vice President, Cimplifi 🎙️ Tim Prowitt, Head of Sales, PromptArmor 🎙️ Mark Redmayne, Senior Director of Legal Services, TCDI 🎙️ Shaunak Turaga, CEO, Docsum

I spoke with Hilary Bowman, a healthcare attorney, who is the Founder of Querious, an application that facilitates virtual lawyer-client conversations using generative AI. We discussed how artificial intelligence can help legal professionals optimize client conversations, the value of real-time legal insights, and how the attorney-client relationship is evolving.

I spoke with Ruchie Chadha, the President of Smokeball US, an AI-powered legal practice management software platform that helps small law firms stay organized, productive, and profitable. We discussed the importance of trust accounting, empowering lawyers by partnering with state bar associations, and leveraging technology to reshape the competitive landscape for solo practitioners and small firms.

I spoke with Matthew Rasmussen, the CEO, and Ryan Frye, the Chief Innovation Officer, at ModeOne, a targeted remote smartphone data collection provider. We discussed the risks involved in extracting company data from personal devices, the biggest misconceptions about mobile data collection, and how organizations can ensure their mobile data collection processes align with evolving privacy laws and regulatory requirements.

I spoke with Ted DeBettencourt, a Co-Founder of Juvo Leads, a company that provides human-powered chat services. We discussed the benefits of human-powered chat for law firms, use cases where prospective clients prefer technology to human interaction, and the mistakes professional services firms make when deploying human-powered chat.

I spoke with Uwais Iqbal, the Founder of Simplexico, a UK-based AI consulting firm helping legal teams with AI adoption. We discussed the most common use cases for generative AI, how legal professionals can maximize their use of generative AI, whether law firms should build or buy generative AI applications, and how the use of AI in law firms is evolving.

I spoke with Katya Fisher, CEO of Aracor, a software platform to streamline M&A, private equity, and venture capital transactions. We discussed the evolving M&A lifecycle, the changing relationship between in-house counsel and outside counsel, and how AI has changed M&A and corporate transactions.

I spoke with Danny Thankachan, the Head of Partnerships at CaseGuild, an AI-powered platform that finds key evidence in litigation. We discussed how legal teams can use artificial intelligence to find crucial evidence, ways that lawyers are currently trying to solve this problem, and the ideal users of this technology.

In this 40th episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed bringing back boring, legal operations trends, and embracing automation.

I spoke with Ciprian Şaramet, Managing Director of Modular Services, a Romanian company focused on providing technical support and business services to global law firms. We discussed how law firms can strengthen their cybersecurity posture, the influence of AI on law firm security, vulnerability management, and the value of continuous education for safeguarding client data and firm operations.

I spoke with Matt Tait, the CEO of Decimal, a tech-enabled services firm focused on bookkeeping, tax filings, and tax preparation. We discussed how the economy is affecting the way law firm leaders manage their practices, the business mistakes they are making, ways to balance the application of technology and talent, and best practices for leveraging technology to maintain books and records.

I spoke with Thomas Bueler, the Co-founder and Chief Product Officer at Vecflow, a legal AI platform designed to help lawyers review and draft documents for use cases in M&A and class action litigation. We discussed the role of AI in expanding legal workflows, the importance of minimizing hallucinations in large language models, and the best practices for evaluating different AI products.

I spoke with Laurie Ehrlich, the chief legal officer, and Farah Gasmi, co-founder and chief product officer at Dioptra, an AI-powered contract redlining and playbook generation tool. We discussed the difference between RAG and Agents in AI, the challenges associated with AI adoption, and how lawyers can secure buy-in for new AI tools more effectively.

I was fortunate to speak with these leaders on the third day of Legalweek 2025 for this #ReinventingProfessionals #Mixtape:

Valerie Chan, CEO, Plat4orm Dan Ruderman, Director, Strategic Alliances, LexisNexis Legal - CounselLink   Alex Sappington, Co-CEO, Page Vault  

*Background music credit: Upbeat Indie by Lowtone Music

In this 39th episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed Legalweek 2025, Skills.Law, generative AI use cases, and accelerating innovation in legal.

I was fortunate to speak with these leaders on the second day of Legalweek 2025 for this #ReinventingProfessionals #Mixtape:

*Background music credit: Upbeat Hope by Lowtone Music

I was fortunate to speak with these leaders on the first day of Legalweek 2025 for this #ReinventingProfessionals #Mixtape:

Josh Baxter, CEO, NetDocuments

Milan Bobde, CEO, Oddr

Edward Chick, Chief Revenue Officer, NopalCyber

Dan Hauck, Chief Product Officer, NetDocuments

Brandon Hollinder, Vice President, eDiscovery and Cyber Solutions, Epiq

John Hale, Chief Marketing Officer, Consilio LLC

Scott McFetters, CEO, CoreTech

Michael Murray, Director of Technology and Creative Solutions, Veritext Legal Solutions

Anne Post, CEO, North America, Xakia

Early Stephens, CEO, Actionstep 

Rick Weber, Managing Partner, Arbor Ridge Partners

Chris Williams, Head of Ecosystem & Community, Legora

I was fortunate to speak with these leaders the day before Legalweek 2025 for this Mixtape: Bradley Collins, Co-Founder and CEO, LegalTechTalk Dan Malgran, VP, Marketing, Steno Patricia Nagy, Chief Strategy Officer, The Proxy Agency Alaa Pasha, CEO, Maptician Steven Salkin, Editor-in-Chief, Law Journal Newsletters Abhijat Saraswat, Chief Revenue Officer, Lupl Kelly Twigger, CEO, Minerva26 Beau Wysong, Chief Marketing Officer, Opus 2

*Background music credit: Upbeat Life by AudioCoffee Band

I spoke with Vincent Allen, partner at Carstens, Allen & Gourley, an IP-focused law firm that helps companies with patent, trademark, copyright, trade secrets, and intellectual property strategies. We discussed how current copyright laws address authorship and ownership of AI-created works, strategies content creators can use to protect their intellectual property when AI tools are used, and measures that can be taken to ensure that human creators are fairly compensated and protected.

I spoke with Adam Philipp, the founder of AEON Law, an intellectual property law firm. We discussed the benefits of fixed-price legal services, how a fixed-price model expedites the adoption of new technology, and best practices for law firms interested in pursuing and implementing innovation-focused initiatives.

I spoke with Edward Chick, the Chief Revenue Officer at NopalCyber, a managed security service provider that offers outsourced cybersecurity support, seeking to democratize enterprise-level security for law firms and organizations in other sectors. We discussed best practices to help law firm leaders identify cyber threats, mistakes they are making with their cybersecurity protocols, how often they should test and update their cybersecurity procedures, and where to leverage artificial intelligence and machine learning to enhance cybersecurity.

I spoke with the following chief executive officers in a CEO Roundtable discussion about challenges and opportunities ahead of Legalweek 2025:

Ray Biederman, Proteus Discovery Group Chris Cartrett, Aderant James Ding, DraftWise Tom Dunlop, Summize Sirisha Gummaregula, QuisLex Scott McFetters, CoreTech Renee Meisel, UnitedLex Sarai Schubert, Hanzo Joey Seeber, Level Legal Todd Smithline, Bonterms

I spoke with Amy Juers, the CEO of Edge Marketing, a marketing and PR agency serving the legal, accounting, and professional services industries. We discussed the benefits of leveraging artificial intelligence in public relations and marketing, how it enhances client service, and the best practices for AI implementation.

I spoke with Jack Weinberger, the Co-Founder of Ajax, an AI company that helps lawyers manage their time. We discussed the need to secure data in AI timekeeping applications, the promise of capturing more time in legal services, and how legal timekeeping is evolving.

I spoke with William Dougherty, the Co-founder and CEO of Capacity, a work allocation solution designed to help law firms optimize their resources. We discussed how Capacity addresses the most common inefficiencies in law firm resourcing, the benefits of optimal work allocation to lawyers and their clients, and how the distribution of legal work is evolving in an AI era.

I spoke with Ray Biederman, the Co-Founder and CEO of Proteus Discovery Group, which is celebrating its 10th anniversary, and is a founding partner of Mattingly Burke Cohen & Biederman. We discussed the genesis of Proteus Discovery Group, the benefits of simultaneously managing a law firm and a legal services company, and how e-discovery is evolving.

In this 38th episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed achieving work-life balance, building momentum in 2025, and preparing for Legalweek.

I spoke with Douwe Groenevelt, Vice President, Deputy General Counsel & Head of Legal at ASML, and a featured speaker at the Lexpo Conference, taking place in Amsterdam on June 16th and 17th. We discussed the mission of Law & Ops, the Tech in Legal initiative, the most significant opportunities for in-house legal teams to innovate, and how AI is reshaping corporate law departments.

I spoke with Doug Kaminski, the Chief Revenue Officer at Infinnium, a data governance platform. We discussed how information governance affects an organization's data security, best practices for organizations to build better data hygiene, and ways that artificial intelligence is affecting these efforts.

I spoke with Lynn Tubalinal, the Director of Litigation Support at Dykema, and Julia Voss, the Director of Litigation Support and eDiscovery at UB Greensfelder. Both are among the industry leaders who contributed to the recently published report - Advancing Litigation Support to Fuel Growth in a Changing Legal Market - supported by Opus 2. We discussed the effect of the increasing volume and variety of data, how a team knows that it is time to upgrade its technology, successful strategies for driving adoption, and effective generative AI use cases.

I spoke with Renee Meisel, the CEO of UnitedLex, a tech-enabled legal services provider. We discussed what differentiates UnitedLex from other providers of legal services, how leaders can promote a culture emphasizing innovation, collaboration, and a unified sense of purpose, and trends driving the most significant change in legal.

I spoke with Daniel Booter, the Director of Marketing of MacroAgility Systems, an iManage partner specializing in integrating tailored solutions and implementations for law firms. We discussed how MacroAgility Systems provides tailored technology solutions for law firms, the problems iSyncKit and Uplift Migration solve, ways to streamline document management, and best practices for optimizing a firm's legal tech infrastructure.

I spoke with Joseph Frantz, the Founder of TimeSentry, an AI native time tracking solution for hourly billing professionals. We discussed how law firms can use artificial intelligence to capture more value from clients and work smarter, ways that organizations currently approach this process, and where legal technology is headed in 2025.

In this 37th episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed the market moves in January 2025, the accelerating pace of change in legal, and AI pitfalls to watch.

I spoke with Josh Smith, the Information Security Manager at Ogletree Deakins, and Ken Jones, a Lecturer at the Seton Hall University Stillman School of Business and the Principal Consultant with Xerdict Group, the technology subsidiary of Tanenbaum Keale. The two leaders are the co-chairs of ILTA's 2025 EVOLVE conference. We discussed how the event will address the unique challenges law firms have with protecting sensitive client data, practical and actionable AI topics, and speakers who will focus on emerging cybersecurity threats. 

I spoke with Chris Williams, the Growth and Partnership Lead at Leya, an AI-powered legal workspace that integrates with firm knowledge systems to automate tasks like due diligence and legal research. We discussed how law firms are implementing generative AI, how they overcome the fear of using AI, best practices for getting started with generative AI, mistakes to avoid when deploying AI, and tips for earning buy-in for new initiatives.

I spoke with Melissa Rogozinski, the founder of RPC Strategies, a growth marketing consulting firm specializing in due diligence, revenue operations, and B-to-B growth marketing, including for organizations in the legal sector. We discussed how legal teams can evaluate the security and compliance of AI products, the risks associated with AI deployment in law firms, the value of a comprehensive security questionnaire in mitigating risk, what investors should consider when assessing the revenue growth potential of legal tech startups, and her eBook.

I spoke with Peter Collins, Chief Revenue Officer of Posthire, a company specializing in continuous workforce screening. We discussed how continuous workforce screening differs from traditional background checks, its advantages for ongoing risk management, and its impact on an organization’s overall security posture.

I spoke with Shashank Pande and Rachita Maker, the co-founders of ekamm8, a new legal innovation and consulting firm. We discussed how technology is transforming traditional legal practices, ways that ekamm8's agentic AI services are revolutionizing contract management and compliance, how leaders in legal should encourage technology adoption, and where innovation in legal is headed.

I spoke with Christian Geyer, the Founder and CEO of Actfore, a provider of artificial intelligence-powered data mining tools for cyber breach incident response. We discussed the most common causes of cyber breaches in legal, the convergence of legal, security, and privacy, and where cyber breach incident response is headed.

I spoke with Daniela Semeco, the Founder of LegalType, a keyboard designed specifically for legal professionals. We discussed the benefits of an adaptable SMART keyboard to a lawyer, how the software behind LegalType integrates with existing legal tech tools to enhance productivity, and how innovation in legal tech is evolving.

I spoke with Elisa Silverglade, the Director of Intelligent Automation at Techromatic, which builds software robots to perform manual tasks for law firms. We discussed the benefits of robotic process automation in legal, skills legal professionals should develop to maintain the distinction between their tasks and those robots can perform, and the limits of robotic process automation.

In this 36th episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed reimagining legal in 2025, showcasing practical innovation, and executing strategic plans.

I spoke with Kara Peterson, the co-founder of descrybe.ai, a free legal research tool that uses AI to democratize access to the law. We discussed how descrybe.ai differs from similar tools, the challenges of using AI in legal, best practices for leveraging AI safely, and the legal problems AI can effectively support.

I spoke with Bruce Kuennen, the CEO of doeLEGAL, an enterprise legal management (ELM) software and e-discovery services provider recently acquired by Paris-based DiliTrust, which offers integrated solutions for corporate governance, secure data management, and legal operations. We discussed the benefits of the merger, the connection between ELM and corporate governance, and the future of the ELM market.

I spoke with Rick Hellers, the CEO of Scan Logic, the provider of BillSync and APSync, designed to simplify law firm finances. We discussed common law firm financial challenges, how law firm leaders are leveraging technology to address those challenges, and ways they are balancing their clients' interests in e-billing with their billing protocols.