Lead Legal Strategy for One of Canada’s Fastest-Growing Communities
Nestled on the shores of Lake Ontario, an hour east of Toronto, Whitby is projected to grow from 140,000 to more than 200,000 residents by 2031.
That kind of growth demands a legal leader who can keep pace with the community: someone ready to shape policy, guide Council through complex decisions, and help build the framework for a Town in transformation.
This is your opportunity to serve as the Town’s principal legal counsel and Town Solicitor, a role in which your expertise directly shapes the future of a thriving, sophisticated municipality that still holds onto its small-town heart.
Two heritage downtowns, an award-winning marina, growing employment lands, and an ambitious Official Plan: you’ll be at the table as it all comes to life.
The Opportunity
Reporting directly to the Chief Administrative Officer, the Commissioner of Legal and Enforcement Services/Town Solicitor serves as the Town’s principal legal counsel across all areas of municipal law, leading a full-service legal practice for the Corporation and overseeing Municipal By-law Enforcement, Parking Enforcement, and Animal Services.
You’ll lead a team of four direct reports (Associate Solicitor, Senior Law Clerk/Law Clerk-Assistant, Real Estate Law Clerk, and Manager of Enforcement Services) and manage 28 employees within your broader portfolio.
You’ll be a trusted advisor to Council, the CAO, and the Senior Leadership Team, someone whose judgment is sought daily, not just requested. You’ll make an impact by:
- Serving as principal legal counsel on all matters of law affecting the Town (excluding labour/employment), reviewing and advising on the legal implications of Corporate and Council decisions.
- Advising Council and Town officials on statutes, by-laws, and complex legal situations, partnering with staff to resolve issues before they become obstacles.
- Ensuring Council and Corporate actions are grounded in law, safeguarding the Town’s jurisdiction and legal integrity.
- Building and leading a high-performing legal team, including direct oversight of the Municipal By-law Enforcement and Animal Services Divisions.
- Managing and maintaining a full-service legal practice (excluding Labour/Employment) that supports Council, Senior Leadership, and staff across the Corporation.
- Retaining, instructing, and managing external counsel and consultants for major litigation, tribunal matters, and specialized legal work.
- Staying ahead of the curve in municipal law, translating legislative change into practical policy and operational guidance.
- Representing the Corporation before the Ontario Land Tribunal, the courts, and other legal bodies, and leading the Town’s position in alternative dispute resolution.
- Representing the Corporation at community events involving legal and enforcement matters, building the Town’s profile and relationships.
- Advising Town law enforcement officials and negotiating high-value real estate and leasing transactions on the Corporation’s behalf.
- Shaping legislative strategy and bringing recommendations directly to the CAO and Council on proposed legislation and on where new policy is needed.
- Drafting and reviewing agreements, by-laws, and legal instruments that keep the Corporation moving.
- Preparing reports on service delivery, litigation, and other legal matters affecting the Corporation.
- Attending Council meetings as a core voice in municipal decision-making.
- Owning and actively managing the annual budget for Legal and Enforcement Services and setting the department’s strategic goals and priorities.
- Helping shape the corporate policies, plans, and procedures that support the Town’s biggest initiatives.
What You Bring
You are:
- A strategic, self-motivated legal executive who thrives on complexity.
- You build trust quickly (with Council, staff, and external partners) through sharp communication, tact, and sound judgment.
- You don’t just solve legal problems; you anticipate them and bring innovative solutions to the table before they’re requested.
Your credentials include:
- A Juris Doctor or Bachelor of Laws (JD or LL.B.) from a recognized university
- Admission to the Bar in the Province of Ontario
- Good standing membership with the Law Society of Ontario (formerly LSUC)
Your experience includes:
- 10+ years as a solicitor, ideally in a municipal or government environment, with a deep grounding in municipal law, land development, and real estate matters.
- Extensive, hands-on knowledge of municipal, real estate, and land development law, as well as the provincial authorities that govern them.
- Working familiarity with construction law, procurement law, insurance and risk management, litigation, and general commercial law.
- Fluency in the statutes, regulations, and by-laws that shape municipal decision-making, paired with strong research and analytical skills.
- Demonstrated ability to build and manage a departmental budget and to retain and oversee external legal counsel across a range of matters.
- A track record of persuasively communicating (orally and in writing) with Councils, senior leaders, staff, and the public, securing understanding and buy-in for policies and programs.
- Superior presentation, negotiation, and conflict-management skills, backed by strong research capabilities.
- The ability to juggle a varied, demanding workload, draft airtight legal documents and by-laws, think on your feet, and advocate with confidence.
- Experience preparing and presenting matters before courts and tribunals, particularly planning matters before the Ontario Land Tribunal.
- Comfort and proficiency with standard computer applications.
- A valid, unrestricted Ontario Class “G” driver’s licence and access to a personal vehicle.
What Whitby Offers You
- Compensation: $221,072 to $251,218 per annum (Salary Band 3 of the Management/Exempt/Non-Union group).
- A comprehensive benefits and pension program designed to support both your career and your life.
- Flexible work arrangements that put you in control of your time.
- A seat at the leadership table in a municipality where your work visibly shapes the community’s future.
- A culture grounded in Collaboration, Accountability, Respect, and Engagement (CARE), where your leadership sets the tone.
- Hours: Monday to Friday, 8:30 a.m. to 4:30 p.m. (35 hours per week); additional hours as needed.
- Union Affiliation: None.
Whitby is an Equal Opportunity Employer
At the Town of Whitby, our values guide everything that we do.
We celebrate our differences, which is why we are committed to building an inclusive and barrier-free environment for our team.
If you need a specific accommodation during the recruitment process, please let us know, and we will be happy to provide.
Any information received regarding accommodation will be handled confidentially.
Personal information provided is collected under the authority of The Municipal Act, 2001 and the Municipal Freedom of Information and Protection of Privacy Act.
How to Apply
To express interest in this exciting opportunity, email your cover letter and resume to
Patrick Rowan, Partner
Email: prowan@feldmandaxon.com
This job posting is for an existing position with the Town of Whitby.
We do not use artificial intelligence (AI) tools to screen, assess, or select applicants at any stage of the hiring process.
All applications will be reviewed and evaluated by the Feldman Daxon team.