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Tilly Gray Picture

Email to Tilly Gray Tilly Gray

Partner & Director of Transaction Services


t: 416 869 5408
f: 416 350 6901
e: send email

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

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Year of Call

Ontario, 2004


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

Tilly Gray

Tilly Gray is a partner and Director of Transaction Services at Cassels Brock.

Tilly leads the firm’s Transaction Services team, which focuses on continually seeking to improve both the quality and timeliness of the firm’s corporate and transaction-based legal advice and related services. In this role, Tilly co-founded and is responsible for the oversight of FourLines, a business division of Cassels Brock, that assesses, pilots, and implements specialized staffing models, streamlined workflows, and technology.

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, and has taught as a sessional professor at Queen's University, Faculty of Law.

  • Finalist, "Outstanding Lawyer of the Year," Changing Lawyer Awards (2018)
  • International Legal Technology Association
  • Canadian Bar Association
  • Ontario Bar Association
Conferences, Speaking Engagements, Events Conferences, Speaking Engagements, Events