Tilly Gray

Tilly Gray;
Telephone: 416 869 5408
Fax: 416 350 6901

Suite 2100, Scotia Plaza
40 King Street West
Toronto, ON M5H 3C2

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Tilly Gray is a partner at Cassels Brock and co-founder and lead of its FourLines business division.

Tilly’s multi-disciplinary team focuses on continually seeking to improve both the quality and timeliness of the legal advice and related services provided by all of the firm’s practice and industry groups. Acting as the firm’s process improvement incubator and change agent, FourLines is responsible for identifying opportunities to gain efficiency, including through the assessment, pilot, and implementation of specialized staffing models, streamlined workflows, and technology. FourLines team members are currently responsible for due diligence/contract analysis, document automation/preparation, and transaction/case management. In addition, Tilly consults directly with clients of the firm regarding innovative approaches to legal service delivery and the implementation and adoption of new technologies.

Tilly was formerly the firm’s Director of Practice Excellence – Practice Support, where she was responsible for enhancing the culture of knowledge sharing and collaboration among the firm’s members (including through training and mentoring, developing policies and procedures, developing and enhancing precedents and other practice resources, and facilitating the design and implementation of organizational and technical structures to create efficiencies and capture and disseminate the intellectual capital of the firm’s members). Tilly remains active in the legal knowledge management community in Toronto and is a member of the Toronto Legal KM Group.

Prior to that, Tilly was a senior associate in the Financial Services Group. Her practice focused on general corporate, reorganization, and finance matters, representing both borrowers and lenders in a variety of domestic and cross-border secured and unsecured lending transactions. Tilly was involved in the following notable transactions:

  • Acting for the administrative agent and a cross-border syndicate of lenders in a $100 million financing of an NHL team, and a $265 million financing of another NHL team and arena; Acting for an NHL team in a $130 million financing of the team and arena
  • Acting for the administrative agent and syndicate of lenders in a $150 million construction financing for an international hotel chain 
  • Acting for property management and the developer in a $122.5 million financing for construction of a downtown Toronto shopping and entertainment complex

Wanting to provide the same support and mentoring that she received early in her career, Tilly was an inaugural member of the Women’s Practice Development Committee, is an award-winning mentor for her work with the Student Committee, acts as a mentor for many young legal professionals, and is actively involved in mental health initiatives both within the firm and her community.

Tilly frequently presents on topics such as process improvement, legal service delivery, knowledge and change management, innovation, and legal technology and has taught as a sessional professor at Queen's University, Faculty of Law.


Certified Yellow Belt in Legal Lean Sigma and Project Management

Business Essentials for Lawyers (Cont. Ed.), University of Toronto, 2008

LL.B., Queen's University, 2003

B.A., Laurentian University, 1997

Conferences, Speaking Engagements, Events

Ann Watterworth and Tilly Gray Presenting "Innovation in Client Service Delivery"

Tilly Gray Discussing "Going the Extra Inch: Small Solutions with Big Impact" at ILTACON 2019

Tilly Gray, Panelist, Looking at "Disruption in Large Firms and In House Contexts"

Call to the bar

Ontario, 2004


  • International Legal Technology Association (ILTA)
  • Corporate Legal Operations Consortium (CLOC)
  • Women in Sports and Events (WISE)
  • Canadian Bar Association
  • Ontario Bar Association


  • Finalist, "Outstanding Lawyer of the Year," Changing Lawyer Awards (2018)