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.
Confirm your place by 08.28.26 save $400 use code MIDSIZE
Mid-sized firms using AI tools
86%
Clio Legal Trends Report, 2026
ROI multiplier: strategic vs
ad hoc AI
3.9x
Thomson Reuters
2025
1day
Intensive Format
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 leveraging AI-related lateral hiring to strengthen our 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 we 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?
COMING SOON
Speaking Faculty
Practitioners, founders, and researchers defining the new legal landscape.
We will be announcing our full faculty in the coming weeks.
Want to speak?
Have a case study to share?
Contact Us

David Hambourger
Chief Information Officer
Chapman & Cutler
MARKET OPPOURTUNITY
STRATEGY
DIFFERENTIATION

Roy Saxton
Chief Information 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 OPPOURTUNITY
ROI
STRATEGY
WORKFLOWS
DIFFERENTIATION

Linda Moss
Chief Business Development and Marketing Officer
Dykema
MARKET OPPOURTUNITY
STRATEGY
ROI
ADOPTION & CHANGE
DIFFERENTIATION

Sivan Galinsky
Chief Marketing Officer
Barack Ferrazzano Kirschbaum & Nagelberg LLP
MARKET OPPOURTUNITY
STRATEGY
ROI
ADOPTION & CHANGE
DIFFERENTIATION

Melissa Marshall
Industry Specialist
Former Chief Marketing Officer
MARKET OPPOURTUNITY
ROI
STRATEGY
WORKFLOWS
ADOPTION & CHANGE
DIFFERENTIATION

James Wang
Co-Founder
Postilize
STRATEGY
WORKFLOWS
ADOPTION & CHANGE
DIFFERENTIATION

Mark Levin
Chief Marketing & Business Development Officer
Marshall, Gerstein, and Borun LLP
STRATEGY
WORKFLOWS
ADOPTION & CHANGE
DIFFERENTIATION

Brooke Loucks
Director of Strategic Marketing, Communication and Brand
Winston Taylor
MARKET OPPOURTUNITY
STRATEGY
WORKFLOWS
ADOPTION & CHANGE
DIFFERENTIATION

Rachel Shields Williams
Director of AI and Knowledge Management
Bass, Berry & Sims
MARKET OPPOURTUNITY
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 OPPOURTUNITY
ROI
STRATEGY
WORKFLOWS
DIFFERENTIATION
Expert Voices
Build Your Day
Filter by interest and save your personal agenda.
As technology and AI continue to reshape the legal industry, firms face increasing pressure to make strategic investment decisions that drive efficiency, growth, and competitive advantage. But determining where to invest, and whether to build internally or buy externally, requires more than selecting the newest tool on the market. It demands a structured approach that aligns technology decisions with firm goals, budgets, and measurable outcomes.
This session will explore the full lifecycle of successful technology and AI adoption, from budget planning and evaluating build-versus-buy decisions to vetting solutions, piloting new tools, and selecting the right fit for your organization. Attendees will also examine best practices for onboarding, defining KPIs, and measuring ROI to ensure technology investments deliver meaningful and measurable business impact.
Large law firms often have greater resources, larger technology budgets, and dedicated innovation teams, but many of the strategies driving their success can be adapted by firms of any size.
This session will examine how leading firms are leveraging technology, operational excellence, and strategic planning to strengthen client service, improve efficiency, and drive growth. Attendees will explore practical ways to achieve similar outcomes within the constraints of a mid-sized firm budget and staffing model. Through real-world examples and actionable frameworks, participants will learn how to identify competitive gaps, uncover new opportunities for value creation, and develop an internal checklist for evaluating initiatives that align with organizational goals.
The discussion will focus on building sustainable competitive advantages, maximizing technology investments, and finding innovative ways to compete in an increasingly sophisticated legal marketplace.
Mid-size firms compete in a field that is anything but level. The largest firms arrive with deeper benches, bigger budgets, and established brands; advantages no mid-size firm can simply outspend. What a mid-size firm can do is out-think them. Creativity is the great equalizer: it costs little, scales with imagination rather than headcount, and moves faster than a large firm's layers of approval ever could. Creativity is also the bastion of human talent in an AI world.
This session reframes creativity as a discipline anyone can practice on purpose, using brain hacks and processes. Attendees will leave with practical ways to ask sharper questions, borrow boldly from industries the legal world ignores, and turn their firm's size into a feature nimbleness, distinctiveness, and a willingness to try what the giants would never risk. For mid-size firms, original thinking isn't a luxury. It's the most affordable, and mainly untapped, competitive advantage they have.
For the past two years, the legal industry has been focused on adopting AI. Within a few years, however, capabilities like drafting, research, and document review will become table stakes. Every firm will have access to similar technology.
So what happens when AI no longer differentiates firms?
This session explores the next question: how do mid-sized firms build a competitive advantage when everyone has the same AI tools?
Rather than focusing on technology selection, we’ll discuss how firms can use AI to eliminate low-value work while investing more deeply in the things clients actually value, including professional judgment, stronger client relationships, better attorney development, and proactive business development.
Attendees will leave with practical frameworks for evaluating where AI should automate work, where it should augment lawyers, and where firms should deliberately preserve human expertise as a competitive advantage.
What can mid-sized law firms learn from Big Law, and what advantages should they never give up?
In this candid discussion, legal industry leaders who have transitioned between mid-sized and large firms will share firsthand experiences, examining the differences in technology, operations, culture, and client service.
Attendees will gain practical insights into how mid-sized firms can adopt the best practices of larger organizations while leveraging the agility, collaboration, and personalized approach that often make them uniquely competitive.
In an era of rising costs and increasing client expectations, law firms must ensure every investment delivers measurable value.
This session examines how firm leaders can strategically allocate resources across talent, technology, and operations to maximize performance and support long-term growth. Panelists will share approaches for identifying high-impact investments, leveraging AI and automation to increase efficiency, and empowering teams to accomplish more without expanding headcount.
Attendees will learn how to eliminate operational waste, and create a framework for making smarter spending decisions that align with organizational objectives while maintaining a people-first culture.
Client experience has become one of the most important differentiators for law firms, regardless of size. For mid-sized firms in particular, delivering a consistent and exceptional client experience is critical to strengthening relationships, increasing retention, and driving long-term growth.
This session will explore how firms can move beyond simply providing legal services and create a client-centric culture embedded throughout the organization.
Attendees will hear from award winning law firms on strategies for training and educating teams to build stronger client relationships, aligning internal processes with client expectations, and implementing best practices that proactively identify and meet evolving client needs. Learn how intentional client experience strategies can become a competitive advantage and transform satisfaction into lasting business growth.
Confirm your place by 08.28.26 Save $400 use code MIDSIZE
Registration Options
Law Firm /
Legal Services
Registration
Full Conference Pass
Networking Access
Community Membership
$995
In-house /
Legal Operations
Registration
Full Conference Pass
Networking Access
Community Membership
$795
Solution Providers
Registration
Full Conference Pass
Networking Access
Community Membership
$1,495
Team, Student and Non Proft Rates available
Contact: Have questions or need assistance with the registration process?
Please contact us: contact@insidepractice.com
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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
Heads-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
Register Your Interest
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