Deputy City Solicitor, Planning, Development & Real Estate Law

Job Summary

Reporting to the Director, Legal Services and serving as a member of the Legal Services Management Team, the Deputy City Solicitor provides leadership to the Real Estate, Planning & Development Law Section and oversees the delivery of legal services in support of the City's growth, development and strategic priorities.

This position combines people leadership, legal expertise and strategic business leadership. The successful candidate will lead a team of lawyers, law clerks and legal assistants, fostering a collaborative, respectful and high-performing culture while ensuring the delivery of timely, practical and risk-informed legal advice. The Deputy City Solicitor is a trusted advisor who builds strong relationships across the corporation, provides strategic counsel to senior leaders and Council, and supports the ongoing development of a modern, client-focused legal practice. The role requires strong judgment, political acuity, exceptional interpersonal skills and a demonstrated commitment to mentoring and developing people.

Duties and Responsibilities

Leadership and People Management

• Lead, mentor and support a team of lawyers, law clerks and legal assistants, creating an inclusive, respectful and high-performing work environment.
• Foster employee engagement, accountability, collaboration and professional growth through coaching, mentoring and open communication.
• Promote employee well-being and a positive, respectful and high-performing workplace culture that reflects the City's values and strategic priorities.
• Manage workload distribution and resources to ensure effective service delivery while supporting employee development and success.

Strategic and Operational Leadership

• Participate as a member of the Legal Services Management Team and contribute to the strategic direction, business planning and operational leadership of the division.
• Support modernization initiatives, process improvements and the adoption of technologies that enhance legal service delivery.
• Monitor service levels, operational priorities and emerging risks to ensure responsive and effective client service.
• Contribute to budget planning and the oversight of external legal service expenditures.
• Support divisional and corporate initiatives requiring legal leadership and strategic advice.

Legal Services and Client Advisory

• Maintain a portfolio of complex legal matters while providing strategic oversight of significant planning, development, real estate and Ontario Land Tribunal matters.
• Provide strategic legal advice and representation on planning, development, real estate and growth-related matters, including major development applications, development agreements, land transactions and Ontario Land Tribunal proceedings.
• Advise senior leadership, Council and City staff on matters involving legal, operational, financial and reputational risk.
• Retain and direct external counsel where appropriate.
• Prepare reports and opinions for Council and Committees and attend meetings as required.
• Represent the City in negotiations, mediations, hearings and other proceedings as required.

Relationship Building and Collaboration

• Build and maintain strong working relationships with City departments, senior leadership, Council, external partners and industry stakeholders.
• Represent Legal Services on corporate initiatives, working groups and strategic projects.
• Communicate complex legal issues to diverse audiences in a clear, practical and accessible manner.

Skills and Qualifications

• LL.B. or J.D. and membership in good standing with the Law Society of Ontario.
• Minimum 10 years of progressively responsible legal experience, including significant experience in planning, development and real estate law within a municipal or public sector environment.
• Demonstrated experience leading, developing and managing professional teams in a complex, client-service-driven organization.
• Proven ability to build and sustain a positive, inclusive and high-performing team culture through effective leadership, coaching and mentoring.
• Exceptional interpersonal, communication and relationship-building skills, with the ability to establish credibility and influence with staff, senior leaders, elected officials, clients and external stakeholders.
• Strong political acuity, organizational awareness and judgment in managing sensitive, complex and high-profile matters.
• Strategic and solutions-oriented mindset, with the ability to balance legal risk, operational realities, business objectives and client service expectations.
• Thorough knowledge of municipal planning, development and real estate law, including development approvals, development agreements, land transactions and growth-related matters affecting Ontario municipalities.
• Demonstrated experience negotiating, drafting and advising on complex planning, development and real estate agreements.
• Significant experience providing strategic legal advice on major development applications, planning matters and growth-related initiatives.
• Experience appearing before administrative tribunals, including the Ontario Land Tribunal, and directing complex litigation and external counsel.
• Demonstrated ability to maintain a sophisticated legal practice and manage complex files while leading a team and overseeing a diverse legal portfolio.
• Municipal government experience is strongly preferred.