AI x
MIDSIZE

Mid-sized law firms occupy the fastest-moving segment of the legal AI market. With 86% already experimenting, the question is no longer whether to adopt — it is how to adopt strategically, govern responsibly, and convert efficiency into competitive advantage.

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Mid-sized firms using AI tools

86%

Clio Legal Trends Report, 2026

More likely to see AI benefits

with a strategic plan

3.9x

Thomson Reuters

2025

1day

Intensive Format

OUR EVENT PARTNERS

EIGHT CORE THEMES

What We're Examining

From market opportunity to operational workflow, the eight dimensions shaping AI strategy for mid-sized law firms.

01 / 08

The AI Market Opportunity

The legal AI market hit $5.47 billion in 2025 and is accelerating. Mid-sized firms are uniquely positioned: nimble enough to move fast, large enough to invest meaningfully, and client-close enough to see immediate ROI.

  • How will our firm capture a share of the $5.47B legal AI market?
  • As mid-sized firms adopt AI tools, what is our plan to stay competitive?
  • How can you leverage AI-related lateral hiring to strengthen your talent pool?

02 / 08

AI Stack Selection: Build, Buy, or Integrate

The mid-market stack decision is the most consequential technology choice in a generation. Embedded AI within existing platforms vs. specialist point solutions vs. custom-built — each path carries distinct risk, cost, and capability profiles.

  • Has your firm formally adopted generative AI?
  • Should you invest in specialist point solutions or broader platforms?
  • How does the Clio/vLex acquisition change your perspective on unified research and practice management?

03 / 08

Governance That Fits

Only 44% of firms have governance policies for AI, yet ~500 AI hallucination cases have already surfaced globally. Mid-sized firms need governance that is proportionate, practical, and embedded — not borrowed from Big Law compliance playbooks.

  • How can you lead the way on governance policies?
  • What is your AI hallucination risk mitigation strategy?
  • Is our formal AI policy robust enough to meet rising industry standards?

04 / 08

Workflow Wins: Drafting, Research, Discovery, Intake

The immediate ROI from AI sits in four workflow categories. Firms reporting 80%+ daily AI usage are already seeing transformative efficiency gains across drafting, legal research, document review, and client intake.

  • Can you achieve a reduction in due diligence time through automation?
  • What infrastructure is needed to reach daily AI usage?
  • How will we manage the increase in work volume enabled by AI?

05 / 08

Knowledge & Precedent Modernization

AI is only as good as the knowledge infrastructure underneath it. Mid-sized firms that invest in taxonomies, precedent libraries, and structured work product now will compound those advantages as AI capabilities expand.

  • How are you ensuring knowledge quality, given it is the #1 determinant of AI success?
  • What steps can we take to achieve structured KM?
  • How quickly can you implement precedent banks to accelerate drafting?

06 / 08

Pricing & Profitability in an AI Era

If AI cuts drafting time by 50%, hourly billing means you just halved your revenue on that task. Mid-sized firms must rethink pricing models — moving toward value-based, fixed-fee, and outcome-driven structures that capture the productivity dividend.

  • How will you use AI as a competitive differentiator?
  • Can you boost client satisfaction?
  • How do you transition to value-based pricing?

07 / 08

Adoption & Change Management

Technology selection accounts for only 20% of successful AI deployment. The remaining 80% is change management — training, incentive alignment, workflow integration, and sustained cultural reinforcement across the firm.

  • How do you engage your professionals already using AI tools?
  • What is our roadmap to achieve the ROI?
  • How will training investment directly impact the depth of the firm's adoption?

08 / 08

AI-Driven Differentiation

AI is becoming the primary axis of competitive differentiation for mid-sized firms. Those that move from efficiency gains to client-facing AI products, predictive analytics, and proactive advisory will pull ahead permanently.

  • In what ways will AI become your primary differentiator?
  • How can we develop client-facing AI products?
  • Are you securing first-mover advantages as AI models continue to compound?

CONFIRMED SPEAKERS

Speaking Faculty

Practitioners, founders, and researchers defining the new legal landscape.

Additional speakers will be announced.

Want to speak?

Have a case study to share?

Contact Us

David Hambourger

Chief Information Officer

Chapman and Cutler LLP

MARKET OPPORTUNITY

STRATEGY

DIFFERENTIATION

Roy Sexton

Chief Marketing & Client Development Officer

Vedder

STRATEGY

ADOPTION & CHANGE

DIFFERENTIATION

Alex Schnepf

Head of Legal Engineering

Harvey 

AI

STRATEGY

ROI

GOVERNANCE

ADOPTION & CHANGE

WORKFLOWS

Michael Dov Nogroski

Chief Innovation Officer

Chapman

AI

STRATEGY

ROI

GOVERNANCE

ADOPTION & CHANGE

WORKFLOWS

Morgan Llewellyn

AI Practice Director

HIKE2

AI

MARKET OPPORTUNITY

ROI

STRATEGY

WORKFLOWS

DIFFERENTIATION

Linda Moss

Chief Business Development and Marketing Officer

Dykema

MARKET OPPORTUNITY

STRATEGY

ROI

ADOPTION & CHANGE

DIFFERENTIATION

Sivan Galinsky

Chief Marketing Officer

Barack Ferrazzano

MARKET OPPORTUNITY

STRATEGY

ROI

ADOPTION & CHANGE

DIFFERENTIATION

Melissa Marshall

Chief Branding Marketing & Business Development Officer

 Riley Safer Holmes & Cancila LLP

MARKET OPPORTUNITY

ROI

STRATEGY

WORKFLOWS

ADOPTION & CHANGE

DIFFERENTIATION

Rachel Shields Williams

Director of AI and Knowledge Management

Bass, Berry & Sims

MARKET OPPORTUNITY

STRATEGY

WORKFLOWS

ADOPTION & CHANGE

DIFFERENTIATION

James Wang

Co-Founder

Postilize

STRATEGY

WORKFLOWS

ADOPTION & CHANGE

DIFFERENTIATION

Mark Levin

Chief Marketing & Business Development Officer

Marshall, Gerstein & Borun LLP

STRATEGY

WORKFLOWS

ADOPTION & CHANGE

DIFFERENTIATION

Brooke Loucks

Director of Strategic Marketing, Communications and Brand

Winston Taylor

MARKET OPPORTUNITY

STRATEGY

WORKFLOWS

ADOPTION & CHANGE

DIFFERENTIATION

Jennifer Musser

Director of Business Development

Chapman and Cutler LLP

MARKET OPPORTUNITY

STRATEGY

WORKFLOWS

ADOPTION & CHANGE

DIFFERENTIATION

Sally Rouse

President of Business Operations

Oliva Gibbs

ROI

PRICING & PROFIT

AI

STRATEGY

WORKFLOWS

ADOPTION & CHANGE

Paula Smith

Controller

Oliva Gibbs

ROI

PRICING & PROFIT

AI

STRATEGY

WORKFLOWS

ADOPTION & CHANGE

Jeanne Hammerstrom

 Chief Marketing Officer

Benesch Friedlander Coplan and Aronoff LLP

MARKET OPPORTUNITY

ROI

STRATEGY

WORKFLOWS

DIFFERENTIATION

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Join AI x Midsized in Chicago

A focused day for managing partners, CIOs, COOs, and innovation leads at mid-sized law firms — the practical playbook for AI that delivers measurable ROI.

Practitioner-Led Sessions

Managing partners and CIOs from firms share what actually works — and what doesn't.

Live Platform Demonstrations

Hands-on time with today's leading AI and Legal Tech solution providers

ROI Workshop

Interactive session: building the business case and measuring AI returns for the mid-market.

Peer Roundtables

Structured discussion by firm size, practice area, and implementation stage.

Inside Practice Research Pack

Full market analysis delivered pre-event; session recordings and resource library post-event.

EVENT DETAILS


📅 November 5, 2026
📍 Offices of Chapman and Cutler in Chicago, IL

👥 100+ Mid-Sized Firm Leaders

🎫 Law Firm, In-House, and Vendor passes available

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