Agenda at a Glance
2026 AI Native Law Conference
Morning
Arrival, Breakfast, and Networking
Opening Remarks
Patrick DiDomenico, Founder and CEO, LegalTech Connect Matt Pollins, Co-Founder and Chief Product Officer, Lupl; Founder, The AI Native Firm Index
Keynote: The Future of Legal is Built on Data
Mark Smolik, Chief Legal Officer, DHL Supply Chain Americas
Description
Data is the foundation. Without it, no technology investment will deliver the results it is capable of. Since 2009, Mark Smolik has built the DHL legal department on a P&L model founded on data aggregation and disciplined operations, bringing work in house, expanding into commercial contracts and regulatory operations, and spending the past three years deploying AI tools with IT and partners.
Designing and Structuring an AI Native Law Firm
Elliott Portnoy, Global CEO Emeritus, Dentons; Strategic Advisor for Investment Legal Sector Joshua Porte, Partner and Co-Leader, Legal Services Transactions Team, Holland & Knight Moderator: Jenn McCarron, Co-Founder and CEO, Contracts.ai
Description
What makes a law firm AI native, and what does it take to design one? The session examines what makes AI native firms different, then turns to creation: entity design, management service organizations (MSO), alternative business structures (ABS), outside capital, non-lawyer ownership restrictions, and professional responsibility considerations on independence, supervision, and fee sharing. It separates what is settled, what is state specific, and what remains open.
Morning Networking Break
Midday
The Cost of Elite Legal Representation Has Collapsed: How One Law Firm Hired AI to Replace Associates
Michael Showalter, Founder, Showalter PLLC
Description
With an AI-savvy senior lawyer at the helm, AI now outperforms the median human associate. Michael Showalter started a solo litigation boutique in March 2026 and often charges less than one tenth of what a traditional firm would cost. He shows what an AI-native firm looks like day to day and issues a challenge to every lawyer still waiting.
Midpage x Showalter: How to File Elite Briefs Without Opening Westlaw
Otto Zastrow, CEO and Founder, Midpage Michael Showalter, Founder, Showalter PLLC
Description
Using real briefs, Otto Zastrow and Michael Showalter show how Michael conducts legal research by prompting Claude in English with Midpage running underneath, rather than devising boolean searches, and how his AI tools cite-check his own briefs and flag opposing counsel's hallucinations and mischaracterizations.
Inside the AI-Native Legal Department
Laurie Basch, Associate General Counsel, McKinsey & Company Elizabeth Spector Louden, Former VP and Deputy General Counsel, Etsy; Founder and Managing Partner, Spector Louden Law PLLC Erica Swainson, VP, Legal Innovation and Strategic Initiatives, Salesforce Moderator: Ken Crutchfield, Founder and CEO, Spring Forward Consulting
Description
Corporate legal departments have run on AI-native principles for years: fixed budgets, playbooks, automation, and success measured by outcomes rather than hours. If you designed your department today, how would you build it? In-house leaders share what stays in house, what moves out, what needs to change, and what they now expect from outside counsel and vendors.
Lunch and Networking
Afternoon
Legal AI Value Stack: A Working Roadmap to "AI-Native"
Helen Fan, Chief AI Officer, MagStone Law; Founder, Legal Tech Frontier and Helen's Legal AI Lab
Description
Helen Fan gathered 50 people in Silicon Valley to wrestle with one question: what is an AI-native law firm? She shares where that conversation landed and offers her own answer through the Legal AI Value Stack, a framework refined through her hands-on 100-day agent experiment. The one thing that matters most in becoming AI-native is not the tools.
Can AI Native Law Firms Compete with Traditional Law Firms?
Avi Gesser, Partner and Co-Chair, AI, Cybersecurity, and Privacy Practice Group, Debevoise & Plimpton Sanjay Kamlani, Co-founder and Partner, FairPlay Law; Innovation Advisor, Holland & Knight Liz Paisner, Managing Partner, General Legal
Description
Can AI native firms win the trust, judgment, and relationships incumbents have built over decades? Can traditional firms defend their position against rivals with lower costs, fixed pricing, and capital to spend? The session looks at where AI-native models are gaining ground, where established firms still hold the advantage, and how the market may split, drawing on economics, client demand, regulation, and capital.
Build, Buy, or Blow It Up: The Path Is in the Math
Rob Saccone, Partner, Nexlaw Partners Jeffrey Sharer, CEO, LexShift; Founder and Principal, Sharer Law
Description
Incumbent firms, individual partners, and practices are asking what "AI-native" means for them. Rob Saccone and Jeff Sharer frame the real strategic choices: buy off-the-shelf AI, build your own capability, or rethink the model entirely. They dig into what changes the economics of legal work and what is just an old model with new software.
Afternoon Networking Break
Post-Scarcity Legal: What Happens When Legal Advice Stops Being Scarce?
Ryan Walker, Co-Founder and CEO, General Legal
Description
Legal help has always been rationed by price, and whole categories of legal work never get done because the cost is prohibitive. Ryan Walker built General Legal on a bet that this era is ending. If a high-quality contract review costs $500 and arrives before lunch, what changes for clients, for firms, and for everyone who could never afford a lawyer? He argues the second-order effects will be far bigger than the efficiency gains.
Outside Money, Inside Pressure: Funding the AI Era of Law
David Perla, Vice Chair, Burford Capital Lee Minkoff, Managing Director, Renovus Capital Partners Richard Perris, President and Co-Founder, Covenant Moderator: Patrick DiDomenico, Founder and CEO, LegalTech Connect
Description
Outside investors are backing AI-native law firms built from scratch, putting hundreds of millions behind a model designed to compete with incumbents on speed and cost. Traditional firms are spending more on AI and R&D than ever, straining a partnership structure never built to fund heavy technology investment. The session examines how outside capital is entering legal services through new ownership structures and how the pressure to fund AI is changing the economics and independence of established firms.
Open Forum Discussion
Facilitators: Rick Merrill, Managing Partner, Merrill Jen Berrent, CEO and Co-Founder, Covenant
Description
The facilitators set the stage, frame the topics, and surface open questions. Then the room takes over. Attendees bring their ideas, experiences, and conclusions. The AI Native Law Community is still being defined, so every participant has something to add.
Closing Remarks
Patrick DiDomenico, Founder and CEO, LegalTech Connect Matt Pollins, Co-Founder and Chief Product Officer, Lupl; Founder, The AI Native Firm Index
Evening
Networking Reception
Cocktails, hors d'oeuvres, and continued conversation.