Senior Legal Counsel, Labour & Employment in North York, ON

July 21, 2025

This is an excellent opportunity for an experienced and highly skilled lawyer to join a competent, high-functioning and professional in-house Legal Department, reporting to the Executive General Counsel and Head of Legal Services of the Toronto Catholic District School Board (“TCDSB” or “the Board”).

The TCDSB is one of the largest school boards in Canada and the largest Catholic school board in the world, serving approximately 87,000 students in nearly 200 Catholic schools in the City of Toronto.

At TCDSB, the Executive General Counsel is responsible for the Legal Services department and ensures most of the Board’s legal work is done in-house. The Legal Services team functions like a boutique law firm, providing advice and representation on a variety of legal areas – labour and employment law, contracts, litigation, privacy, real estate, administrative and constitutional law, corporate governance and more.

Job Description – Senior Legal Counsel, Labour & Employment

Reporting to and under the direction of the Executive General Counsel, the Senior Legal Counsel will provide legal advice and representation on a broad range of labour and employment law files.

As Senior Legal Counsel, Labour & Employment, you will be responsible for representing the Board at labour mediations and arbitrations, preparing legal submissions, researching case law, and advancing the Board’s interests at mediations, settlement discussions and arbitration. You will also be responsible for providing legal advice on legal issues arising from day to day with respect to the Board’s employees – both unionized and non-unionized.

As the ideal candidate, you will have a minimum of fifteen years of labour law experience and at least ten years of experience independently conducting labour mediations and litigating labour arbitrations. Public-sector experience is strongly preferred.

Key Accountabilities and Responsibilities

· Represent the Board at labour grievance mediations and arbitrations.
· Prepare legal submissions for filing at various labour and other related tribunals.
· Provide legal advice to Board leadership (e.g. Superintendents, Principals, Vice-Principals, Business Leaders and Human Resources professionals) on legal matters related to their rights, responsibilities and duties as leaders in a highly unionized environment (i.e. working with collective agreements and applicable legislation), and as leaders supervising non-unionized staff.
· Advise on the implementation of resolutions in labour matters from a legal perspective.
· Provide legal advice on disciplinary matters and the implementation of discipline as appropriate.
· Provide legal advice as needed to support the development of negotiation strategies and bargaining activities.
· Research and prepare legal opinions and memoranda for the Executive General Counsel on labour and employment law matters.
· Collaborate with the Executive General Counsel in supporting the vision for the Board’s legal services.
· Assist in drafting reports on legal matters as directed by the Executive General Counsel to support Board functions.
· Remain current on developments of relevant legal updates and issues.
· Adhere to the highest standards of professional and ethical conduct.
· Perform such other duties and tasks as directed by and to support the Executive General Counsel.

Education and Professional Skills/Knowledge

· LL.B. or J.D. degree (or equivalent).
· Good standing with a Canadian Law Society.
· Minimum of 15 years related experience practicing labour law, including collective bargaining and labour arbitrations.
· Proven track record of attending and advising on labour arbitrations.
· Ability to work in a fast paced and rapidly changing environment.
· Ability to analyze legal risk in context of business realities and provide practical advice focused on the ‘big picture’ goals of the Executive General Counsel and the Board.
· Experience with management-side labour law in the public sector is preferred, as is experience with multi-unionized environments.
· Exceptional communication and interpersonal skills.
· Ability to work independently while being an effective member of a team.
· Prepared to contribute, learn and develop with a flourishing, high-functioning legal team focused on excellence in service delivery and results.

The TCDSB is strongly committed to fostering and creating a diverse and inclusive workplace that reflects the stakeholders and communities we serve. As such, we welcome and encourage applications from candidates who self-identify as members of groups protected by the Human Rights Code (including but not limited to racialized persons, persons with disabilities, Indigenous and Aboriginal peoples, and women).You are invited to voluntarily indicate if you identify as one or more of the aforementioned groups. This information will be kept confidential.

This is an exclusive search.

The Counsel Network (part of Caldwell) is committed to building a diverse legal community through our inclusive business and recruitment practices. We value diversity of experience, expertise, and background, and strive to eliminate barriers historically encountered by marginalized groups. We recognize that an equitable, diverse, and inclusive workforce benefits and enriches both the legal profession and the greater community.

To apply for this position: https://caldwell.thriveapp.ly/job/1247

For more information or to apply for this position, contact:
Meaghan Loughry, Consultant
mloughry@caldwell.com
647.417.4720