Assistant Town Solicitor

Oakville; Oakville; Hybrid; CAD 120,000 - 180,000; Full time

Benefits offered by this job

Health plan

Life and disability insurance

Work-life balance

Job summary

The Town of Oakville is seeking an Assistant Town Solicitor to provide strategic legal services to staff and Council on municipal and planning matters. The role involves representing the Town in litigation, negotiating agreements, and drafting by-laws with a focus on public interest and governance.

Qualified candidates hold a Law degree, be licensed in Ontario, and have strong advocacy, negotiation, and leadership skills. A CRJMC check will be required.

Qualifications

• LL.B. or J.D. and licensed to practice law in Ontario.
• Minimum 8 years of related municipal and planning and development law experience.
• Active in good standing with the Law Society of Ontario.
• Experience advocating before the Ontario Land Tribunal is an asset.
• Experience advising municipal and/or broader public sector clients.

Responsibilities

• Provide timely, strategic legal services and advice to Town staff and Council on municipal and planning law.
• Represent the Town in arbitrations, mediations, and litigation before courts and tribunals (e.g., Ontario Land Tribunal).
• Negotiate and draft legal documents reflecting applicable policies; advise on by-laws and agreements.
• Develop legal strategies, gather evidence, conduct research, and present arguments and opinions.
• Instruct external solicitors as needed; advise across multi-disciplinary teams.

Skills

Leadership

Negotiation

Advocacy

Communication

Interpersonal

Presentation skills

Analytical

Problem-solving

Education

LL.B./J.D. (Ontario licensure)

Job description

Posting Status

Open to all current Town of Oakville employees and external applicants

Closing Date

Applications for this position must be received at oakville.ca by no later than 11:59 p.m. on November 1, 2026

This job posting is for an existing vacancy and therefore will be filled accordingly.

We offer

• Comprehensive health plan complemented with life and disability insurance
• A progressive work environment that promotes a work/life balance and strives to be a great place for great people to do great things

Reporting to the Town Solicitor, as a member of the in-house Legal Department, the Assistant Town Solicitor serves to safeguard and advance the public interest of the municipal corporation by providing legal services and advice to staff and Council, including representing the Town in litigation and hearings, providing oral and written legal opinions, drafting and reviewing legal documents, including agreements and by‑laws, preparing and reviewing reports, and attending Council meetings.

What can I expect to do in this role?

Responsible for providing timely and strategic legal services and advice relating to all facets of municipal and planning law to Town staff and Council.

Represent the Town in arbitrations, mediations, and litigation proceedings before the courts and administrative tribunals, including the Ontario Land Tribunal.

Negotiate and draft legal documents that reflect applicable policies.

Develop legal strategies, gather and prepare evidence, conduct legal research, and prepare and present legal arguments and opinions.

Make and explain decisions with respect to interpretations of legislation and by‑laws.

Act as instructing counsel to external solicitors.

Work with multi‑disciplinary groups to determine the best way to regulate matters and deliver municipal services.

A Bachelor of Laws (LL.B.) or Juris Doctor (J.D.) and qualified to practice law in Ontario.

Amember in good standing with the Law Society of Upper Canada with a minimum of 8 years’ related experience in municipal and planning and development law.

Experience in advocacy before the Ontario Land Tribunal is considered an asset.

Experience providing legal services and advice to municipal and/or broader public sector clients.

Experience negotiating, structuring, drafting, interpreting, and providing legal counsel and services on various types of legal documents, including agreements and by‑laws.

Your strengths include demonstrated leadership, interpersonal, communication, and advocacy skills, as well as the ability to manage multiple tasks effectively amidst conflicting demands and tight timelines.

Ability to work both independently and as a collaborative member of a hard‑working and collegial team of professionals with a commitment to excellence and client satisfaction.

Strong negotiation, facilitation, mediation, and presentation skills, adaptable for a diverse audience.

Advanced analytical, problem‑solving, research, and decision‑making abilities.

A well‑developed capacity to interpret, anticipate, and convey complex, technical, and abstract information is crucial.

Ability to exercise authority and influence while handling sensitive information and highly confidential matters.

The successful candidate must hold a valid and unrestricted Ontario Driver’s License Class G minimum and will be required to supply their own personal vehicle for performing job duties/corporate business.

Please note that this position requires a satisfactory criminal record and judicial matters check (CRJMC) dated within the last 60 days as a condition of employment.

Core Knowledge Required for Success

You have good knowledge of municipal and planning law legislation, including the Municipal Act, 2001, Planning Act, Building Code Act,1992, Development Charges Act, 1997, and other statutes and regulations pertaining to the work of a municipal lawyer, good knowledge of applicable common law, and an ability to learn and apply corporate and departmental policies and procedures.

In addition, your experience demonstrates the following leadership competencies:

• Strategic Thinking –thinking things through
• Engagement –working effectively with people, organizations, and partners
• Management Excellence –delivering results through own work, relationships, and responsibilities
• Accountability and Respect –serving with integrity and respect

Corporate Values

• Teamwork
• Accountability
• Dedication
• Honesty
• Innovation
• Respect

DATED: October 9, 2026

The Town’s recruitment software includes elements of artificial intelligence to assist in the screening and short‑listing of qualified candidates.

This job profile reflects the general requirements necessary to perform the principal functions of the job. This does not include all of the work requirements of the job. Applicants are required to demonstrate through their application and in the interview process that their qualifications match those specified. Applicants may also be required to undergo testing.

We thank all applicants and advise that only those selected for an interview will be contacted.