Arrive early so you can fully enjoy a wonderful breakfast and network with the brightest minds in the AI Native Law Community. 

Patrick DiDomenico, Founder & CEO, LegalTech Connect 
Matt Pollins, Co-Founder & Chief Product Officer, Lupl / Founder, The AI Native Firm Index

Don't send in the crew before you order the lumber.

Data is the foundation. Without it, no technology investment will deliver the results of which it is capable. That philosophy separates organizations that extract real AI value from those that accumulate expensive tools that underdeliver.

Since 2009, Mark Smolik has built the DHL legal department on a P&L model founded on data aggregation and disciplined operations. He brought work in-house, expanded to commercial contracts and regulatory operations, and spent the past three years deploying AI tools with IT and partners. Under Mark’s leadership, his legal department’s use of data and AI is widely recognized as among the most innovative in the legal industry.

Mark Smolik, Chief Legal Officer, DHL Supply Chain Americas

What makes a law firm AI native, and what does it take to actually design one? This foundational session sets the stage for the day. It starts by examining what makes AI native firms different: designed around AI from day one, with agentic workflows, legal engineering, structured knowledge, and pricing tied to outcomes rather than hours. It 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 that shape decisions. We will separate what is settled, what is state specific, and what remains open. Attendees will leave with a practical road map for building, or becoming, an AI-native law firm.

Elliott Portnoy, Global Chief Executive Officer Emeritus, Dentons | Strategic Advisor for Investment Legal Sector
Joshua Porte, Partner & Co-Leader, Legal Services Transactions Team, Holland & Knight LLP
Moderator: Jenn McCarron, Co-Founder & CEO, Contracts.ai

Enjoy refreshments and network with the brightest minds in the AI Native Law Community.

With an AI-savvy senior lawyer at the helm, AI now outperforms the median human associate by a long shot. When Michael Showalter realized this in March 2026, he started a solo litigation boutique. Other law firms continue to charge for teams of associates—and even paralegals and secretaries, remarkably enough—with a billable-hour model that disincentivizes productivity gains. But Showalter PLLC is destroying litigation expense, often charging less than one tenth of what a traditional law firm would cost. That is possible because the firm is aggressively leveraging AI.

In this talk Mr. Showalter shows what an AI-native firm looks like day to day—and issues a challenge to every lawyer still waiting: the tools to build the practice you want are already here. All that’s left is the nerve to make it happen.

Michael Showalter, Founder, Showalter PLLC 

Otto Zastrow, CEO of Midpage, joins Michael Showalter, Founder of Showalter PLLC, to discuss how he handles legal research. Using real briefs, they will 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 not only cite-check his own briefs but also flag opposing counsel’s hallucinations and mischaracterizations. 

Otto Zastrow, CEO & Founder, Midpage
Michael Showalter, Founder, Showalter PLLC 

Corporate legal departments have quietly run on AI-native principles for years: fixed budgets, playbooks, automation, and success measured by outcomes rather than hours. Now, as AI copilots and agents reshape legal work, in-house leaders face a new question: if you designed your department today, how would you build it? General counsel, legal operations, and innovation leaders share what an AI-native legal department really looks like.  They'll explore and share: what stays in-house, what moves out, what needs to change, and what they now expect from outside counsel and vendors.

Laurie Basch, Associate General Counsel, McKinsey & Company
Elizabeth Spector Louden, Former VP & Deputy General Counsel, Etsy / Founder & Managing Partner, Spector Louden Law PLLC
Erica Swainson, VP, Legal Innovation and Strategic Initiatives, Salesforce
Moderator: Ken Crutchfield, Founder & CEO, Spring Forward Consulting

Enjoy a delicious lunch and network with new friends and colleagues in the AI Native Law Community.

This past May, Helen Fan gathered 50 people in Silicon Valley to wrestle with one question: What is an AI-native law firm? Everyone uses the term, few can define it. Helen shares where that conversation landed and offers her own answer through the Legal AI Value Stack, her framework that began as a theory about defensibility in a post-SaaS world and evolved, through her hands-on 100-day agent experiment, into a working map of AI transformation. She'll cut through the hype to the one thing that matters most in becoming AI-native, and it isn't the tools. A sharp take from a practitioner and community builder, on a term everyone uses but few truly understand.

Helen Fan, Chief AI Officer, MagStone Law | Founder, Legal Tech Frontier & Helen's Legal AI Lab

Can AI native firms win the trust, judgment, and relationships that incumbents have built over decades? Can traditional firms defend their position against rivals with lower costs, fixed pricing, and capital to spend? This session examines both sides of the competition. We will look at where AI-native models are gaining ground, where established firms still hold the advantage, and how the market may split between them. The discussion will draw on economics, client demand, regulation, and capital. Founders, firm leaders, and investors will leave with a sharper view of who is positioned to succeed, and what each must do to thrive in an uncertain future.

Avi Gesser, Partner and Co-Chair of the Artificial Intelligence, 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

"AI-native" isn't just for boutiques or startups with a clean slate. Incumbent firms, and increasingly individual partners and practices, are asking what it means for them. Rob Saccone, Partner at Nexlaw, is joined by Jeff Sharer, CEO of LexShift and Founder of Sharer Law, to frame the real strategic choices: buy off-the-shelf AI, build your own capability, or rethink the model entirely. Jeff has lived all three, from inside Big Law to launching an AI-native practice before anyone used the phrase, while Rob has spent his career helping firms apply new technologies and stand up new models. Together they dig into what actually changes the economics of legal work, and what's just an old model with new software.

Rob Saccone, Partner, Nexlaw Partners
Jeffrey Sharer, CEO, LexShift / Founder & Principal, Sharer Law 

Enjoy refreshments and network with the brightest minds in the AI Native Law Community.

For most of history, legal help has been rationed by price. Whole categories of legal work simply never get done because the cost is prohibitive. Ryan Walker built General Legal on a bet that this era is ending: his AI-native firm delivers senior-lawyer contract work at a flat fee, in hours instead of days, at a fraction of traditional cost. This talk takes that shift seriously and asks what follows. 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 at all? Walker argues the second-order effects will be far bigger than the efficiency gains, and that the scarcest things in law will no longer be legal knowledge or lawyer time.

Ryan Walker, CoFounder & CEO, General Legal 

Two forces are reshaping how legal work gets funded. 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. At the same time, traditional firms are spending more on AI and research and development than ever before, straining a partnership structure that was never built to fund heavy technology investment. This session examines both sides: 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.

David Perla, Vice Chair, Burford Capital
Lee Minkoff, Managing Director, Renovus Capital Partners
Richard Perris, President & Co-Founder, Covenant
Moderator: Patrick DiDomenico, Founder & CEO, LegalTech Connect 

After a full day of amazing conversations, let's have one more. Our Facilitators will set the stage, frame the topics, and surface open questions. Then the room takes over. Attendees discuss the issues and bring their ideas, experiences, and conclusions. The full nature of the AI Native Law Community is still being defined, so every participant has something to add. This session is designed to capture the insights, opinions, and ideas of this community.

Facilitators:
Rick Merrill, Managing Partner at Merrill
Jen Berrent, CEO & Co-Founder, Covenant

Patrick DiDomenico, Founder & CEO, LegalTech Connect
Matt Pollins, Co-Founder & Chief Product Officer, Lupl / Founder, The AI Native Firm Index

Cocktails, hors d'oeuvres, and continued conversation.