Inside Legal KM

join the DISCUSSION: TORONTO // MAY 21 // 2026

Automation, Agents, and Scale.

Rethinking Legal Knowledge in the Age of AI.

Super Early Bird: Confirm your place by 03.20.26 and save $300 use code ILKMTOR

KM / AI / INNOVATION / CANADA

Save the date:

Toronto, Inside Legal KM, May 21

Designing the semantic layer, governance, and retrieval architecture that makes legal AI safe to scale.


Law Firms are learning a hard truth: the limiting factor isn’t the AI model, it’s the knowledge environment the model depends on.


Inside Legal KM is a senior, practitioner-led working forum for law firms and in-house legal teams building the next generation of knowledge capability: AI-ready, governed, auditable, and embedded into real workflows.


Taking place in Toronto May 21st, this program will provide a practical, strategic discussion about Knowledge Management as the operating system of modern legal work, and as the foundation beneath drafting systems, search experiences, agentic workflows, client transparency, and defensible governance.


Join your peers, join the discussion.

SUPPORTING PARTNERS

What we’ll focus on in Toronto


  • Redefining Value & Billing: Exploring how AI reshapes client expectations, transparency, and traditional billing models, and the role of KM in supporting consistent, high-value outputs.
  • Data Security & Sovereign Governance: Navigating the critical intersection of KM and risk management, including cross-border data challenges, U.S. storage concerns, and international transfer resistance.
  • Lawyer-First AI Adoption: Moving beyond technical deployment to lead sustainable change by aligning AI tools with real practice-group needs and reducing "tech fatigue."
  • Client-Mandated Restrictions: Developing "AI-restricted" workflows and audit-ready safeguards for matters where clients prohibit or limit the use of generative AI.
  • Knowledge Infrastructure & Data Hygiene: Preparing the "clean data" foundation required to maximize AI performance.
  • Breaking Functional Silos: Strategies for cross-functional collaboration between KM, IT, Research, and Business Development to build a unified firm-wide strategy.
  • The Canadian State of the Industry: A closing strategic look at ROI, KPI setting, and the evolving skill sets required for the next generation of Canadian legal talent.

Key Details

DATE:  Thursday, 21st May, 2026

TIME:  9:00 AM - 5:30 PM EST

LOCATION: Toronto

Inside Legal KM: Toronto


Super Early Bird: Confirm your place by 03.20.26 and save $300 use code ILKMTOR

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Who Attends

Inside Legal KM Toronto is designed for senior leaders responsible for how knowledge is captured, governed, activated, and delivered across legal organizations, including:


  • Chief Knowledge Officers & KM Leaders
  • Knowledge & Innovation Directors
  • Practice Support, PSLs, Knowledge Lawyers, and Legal Training / PD leaders
  • CIOs, IT Leaders, and Enterprise / Data Architects working with KM teams
  • Legal Operations and Practice Operations Leaders
  • Information Governance, Risk, Compliance, and Security leaders involved in AI deployment
  • Partners and practice leaders shaping delivery transformation

Why Attend

This forum is built for leaders who are:


  • Being asked to prove AI value while also controlling risk
  • Navigating tool proliferation and integration complexity
  • Struggling with fragmented knowledge across repositories
  • Trying to standardize governance, retention, and quality signals at scale
  • Under pressure to move from “pilot wins” to production reliability

Our Speaking Faculty

Steering Committee Member

Kate Simpson

Senior Director, Knowledge &

 Innovation, Legal Solutions

Epiq Advisory for Law Firms

Steering Committee Member

Simon Wormwell

Chief, Strategic Enterprise Initiatives

Osler, Hoskin & Harcourt LLP

Steering Committee Member

Jessica Rubin

Director, Practice Efficiency & Innovation

Miller Thomson LLP

Steering Committee Member

Sukesh Kamra

Chief Knowledge & Innovation Officer

Torys LLP

Steering Committee Member

Thai MacDonald

Chief Knowledge and Innovation Officer

Cassels Brock & Blackwell LLP

Tania Djerrahian

Senior Director, Innovation & Knowledge Management

Davies

Sienna Molu

Founder & Principal Lawyer

Molu Law

Adriana De Marco

Senior Director, Knowledge Management, Education & Innovation

Stikeman Elliott LLP

Thomas Sander

Vice President, Product Management 

Thomson Reuters

Our Speaking Faculty


We are curating a senior, practitioner-led faculty for Inside Legal KM: Toronto and welcome proposals from those actively shaping how knowledge is designed, governed, and delivered inside legal organizations.


Would you like to:


  • Share a real-world case study on building AI-ready knowledge foundations (taxonomy, metadata, lifecycle, precedents)?
  • Lead a panel discussion on KM operating models, governance, or retrieval reliability?
  • Facilitate a practical workshop on semantic layer design, embedded KM workflows, or evaluation of retrieval systems?
  • Explore sponsorship or partnership opportunities to engage a senior community of KM, innovation, legal operations, and technology leaders?

Interested in joining us at Inside Legal KM?

Agenda

Thursday, May 21 2026, Eastern Time (ET)

8:00 AM - 9:00 AM

Registration / Breakfast

9:00 AM - 9:10 AM

Chair Persons Opening Remarks

Chairperson

Kate Simpson

Senior Director, Knowledge & Innovation Legal Solutions

Epiq Advisory for Law Firms


9:15 AM – 10:00 AM

Redefining Value in the Age of AI:

Billing, Client Expectations, and Knowledge Strategy in Law Firms

Explore how the integration of AI into legal workflows is reshaping traditional billing models, client communication, and perceptions of value. As clients demand faster turnaround times, increased transparency, and cost reductions driven by AI-enabled efficiencies, law firms must adapt their billing processes and knowledge strategies to meet these expectations without compromising quality or profitability. This session examines the role of Knowledge Management in supporting consistent AI outputs, guiding effective client conversations, and addressing complexities such as multilingual environments, while positioning AI as a strategic tool for delivering sustainable, client-focused value.

Speaker

Jessica Rubin

Director, Practice Efficiency & Innovation

Miller Thompson LLP

10:00 AM - 10:45 AM

From Knowledge to Control:

Governing Client Data Security and Risk in AI-Enabled Law Firms

As law firms integrate AI into knowledge management and legal workflows, the governance and security of client data has become a critical concern. This session examines how KM leaders, IT, and risk teams can collaborate to establish strong governance frameworks that protect sensitive client information while enabling AI adoption. It will explore cross-border data challenges, including client concerns around data being stored in the U.S., notification and consent requirements, resistance to international data transfers, and the growing impact of cyber risk. Attendees will gain practical insight into aligning knowledge strategies, security controls, and AI tools to ensure client data remains secure, transparent, and well-governed without slowing innovation.

Speakers

Sienna Molu

Founder & Principal Lawyer 

Molu Law


Tania Djerrahian

Senior Director, Innovation and Knowledge Management

Davies


10:45 AM – 11:15 AM

Networking AM Coffee Break

11:15 AM - 12:00 PM

A Knowledge-Led, Lawyer-First Approach:

Driving AI Adoption in Law Firms

AI adoption in law firms succeeds or fails at the lawyer level. This session explores how Knowledge Management teams can lead sustainable AI adoption by aligning tools to real lawyer needs, embedding AI into daily workflows, and designing education programs that respect time pressures and reduce fatigue. Attendees will learn how to use KM strategies, prompt education, practice-group champions, and targeted change management to ensure AI delivers practical value, without overwhelming end users.

Speakers

Thomas Sander

Vice President, Product Management 

Thomson Reuters


Sukesh Karma

Chief Knowledge and Innovation Officer

Torys LLP


Adriana De Marco

Senior Director, Knowledge Management, Education & Innovation

Stikeman Elliott LLP

12:00 AM - 12:45 PM

Session to be announced

Coming Soon

Speaker

TBA

12:45 PM - 1:45 PM

Networking Lunch

1:45 PM - 2:30 PM

Leveraging KM When Clients Say No to AI:

Building Governance, Oversight, and Audit-Ready Safeguards

As client expectations around AI usage continue to evolve, law firms must be prepared to support matters where AI use is restricted or prohibited altogether. This session explores how firms can establish clear governance frameworks, internal guidelines, and oversight mechanisms to ensure compliance with client requirements. Attendees will learn practical approaches for designing AI-restricted workflows, auditing and documenting work to confirm non-use of AI, and managing client expectations while minimizing risk and preserving trust.

Speaker

TBA

2:30 PM - 3:15 PM

Clean Data, Smart AI:

Preparing Knowledge Infrastructure to Maximize AI Outcomes for Lawyers

As law firms accelerate the adoption of AI tools, the quality and structure of their underlying knowledge data has become mission-critical. This session explores why clean, well-governed data and a strong knowledge infrastructure are essential to delivering accurate, reliable, and scalable AI outcomes for lawyers. Attendees will learn how data hygiene directly impacts AI performance, how to prepare knowledge assets for AI-enabled workflows, and how firms can leverage employee expertise alongside AI tools to enhance legal work product, efficiency, and confidence in AI-driven results.


Speaker

Thai McDonald

Chief Knowledge & Innovation Officer

Cassels

3:15 PM - 3:45 PM

Networking Break

3:45 PM - 4:30 PM

Breaking Silos:

Building a Multi-Functional Knowledge Management Strategy in Law Firms

Effective knowledge management in law firms cannot live within a single department. This session explores how cross-functional collaboration between Knowledge Management, IT, Practice Innovation, Research, Business Development, and attorneys is essential to building a cohesive and scalable KM strategy. Attendees will learn practical approaches to breaking down silos, aligning priorities across teams, and fostering collaboration that improves knowledge quality, accessibility, and firm-wide outcomes.

Speaker

Simon Wormwell

Chief Strategic Enterprise Initiatives

Osler, Hoskin & Harcourt LLP

4:50 PM - 5:15 PM

Future-Proofing Canadian Legal KM:

AI Strategy, Tooling, and Measurable ROI

Canadian law firms are facing rapid shifts in how knowledge is captured, delivered, and applied, driven by accelerating AI capabilities and changing client expectations. This session explores what it takes to future-proof Knowledge Management by building an AI strategy that is practical, fundable, and measurable. We’ll cover financial investment considerations, how to select and vet tools, onboarding and change management approaches, and how to set KPIs that demonstrate value. Attendees will also examine how AI is influencing client outcomes, reshaping KM strategy (both positively and negatively), and changing hiring and skill requirements for the next generation of KM and legal operations talent.

Speaker

TBA


5:15 PM - 5:30 PM

Chairperson’s Closing Remarks

Chairperson

Kate Simpson

Senior Director, Knowledge & Innovation Legal Solutions

Epiq Advisory for Law Firms

5:30 PM - 6:30 PM

Networking Reception


Join the Discussion

Join your peers and fellow KM, innovation, and legal operations leaders at Inside Legal KM Toronto to:


  • Gain ready-to-implement frameworks for designing KM as firm-wide infrastructure, not a standalone function.
  • Learn from senior practitioners who are already moving beyond pilots to operational, AI-ready knowledge systems embedded in real workflows.
  • Build your network with KM, innovation, IT, and legal operations leaders shaping the future of governed retrieval, semantic layers, and knowledge delivery in legal practice.

Stay tuned, speakers and panels coming soon!


Super Early Bird: Confirm your place by 03.20.26 and save $400 use code ILKMTOR

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